50 for 50: pocketmap — A Printable Reference for a Long Day of Walking

While planning the 50-for-50 walk, I built a custom routing tool that took in a plain-text route file and generated whatever I needed: a .gpx for my watch, a .kml for my phone's navigation, an HTML Street View preview to spot-check the route. In that spirit, I started wondering: could it also generate a printable reference card? Something I could fold up and keep in my pocket.

Version one generated an index card-sized map. I printed it, got out the scissors, trimmed it down — and threw away most of the paper. That's when it hit me how absurd the index card idea was. It was more work for something less useful, all to meet some arbitrary size requirement.

So the goal shifted: pack as useful a reference as possible onto two pages — a single sheet, double-sided. No cutting required. That became the challenge, and pocketmap is the result.

Two Sheets, Two Jobs

pocketmap takes the same plain-text .pois file used by geoassist and generates a two-page PDF:

pocketmap day1.pois > day1.pdf

Page two is the simpler one: a waypoint table showing each stop, its cumulative distance from the start, and the distance to the next stop. Combined with a distance reference chart (centimeters on the printed map → km and miles), it doubles as a checklist. With six waypoints spaced 2–4 miles apart, a 17-mile day starts to feel doable — just a short list of stops to check off. Shira — a seasoned skeptic of my "this will make things easier" projects — actually used it, treating the waypoint table as a table of contents for the day. That's when I knew I was really onto something.

The 1 cm Rule

Page one is the map, and it's more useful than it first appears. The map is scaled so that the entire route fits on a single page, always expressed in a clean ratio: 1 cm = 1 km, or 1 cm = 2 km, or whatever it takes to fit. The scale bar is on the page.

That simple cm rule connects directly to UTM coordinates, which are printed along the edges of the map just like a USGS topographic quad. A GPS device — phone, Garmin watch, or an InReach you're already carrying for messaging — can display your current UTM coordinates. Find those numbers on the map edge, locate the intersection, and you know exactly where you are.

The useful part: this works without a data connection. Your GPS receiver uses satellites, not cell towers. You can be somewhere with no signal and still find yourself on the map in seconds. If UTM is new to you: it initially looks complex, but it's actually straightforward — and a remarkably simple way to jump between a paper map and a digital device. This video is a quick intro.

I carry a small fresnel lens with centimeter markings along the edge. With the map, that lens becomes a measuring tool: lay it down, count centimeters, multiply by the scale. I can estimate how far I've come, or how far to the next stop, in a few seconds.

How It Actually Went

Honestly, the map was more of a satisfying curiosity than a critical tool on our trip. We were in Knoxville, not the backcountry — if something went wrong, we would call an Uber. But there's something genuinely satisfying about making the leap from digital coordinates to paper in a few moments, and having something physically in my pocket that represents the day ahead.

One thing I hadn't anticipated: the fixed scale. On your phone, you zoom in and out constantly, always seeing the same 2–3 inches of map regardless of zoom level. The printed map doesn't do that. At 1 cm = 1 km, you always see the same stretch of ground. That consistency helps maintain a sense of the whole day — something that gets lost the moment you zoom in on your phone.

One real limitation: the map is useless at micro-navigation. Come to a trail fork — left or right? The scale is way too zoomed out to help. For that, you need your phone.

Low Effort, High Value

If you're using geoassist to build your .pois file, the PDF is a free byproduct. Print it, fold it, put it in your pocket. It won't replace your phone — but it gives you something your phone can't: a fixed, at-a-glance view of the whole day that works anywhere.

Download Pocketmap

pocketmap is free to use and modify. Source code on GitHub: github.com/benjisimon/code/tree/main/pocketmap

50 for 50: The Route to a Better Route

Planning the 50 mile walk to mark my 50th birthday proved to be an interesting challenge. The walk would span three days in an unfamiliar city and had a laundry list of needs: scenic and interesting stretches, resupply stops along the way so we could travel light and stay fueled, and as much sidewalk as possible to keep things safe. And of course, strategic bathroom stops. We also wanted a route that made geographic sense across three days — no backtracking, or covering the same ground twice. And the total distance needed to land just under 50 miles, knowing the total would naturally creep up as we went. That's a lot to ask. Here's the tool that helped us pull it off.

AI: Enthusiastic, But Faking It

Like many travel-related tasks these days, we started our planning in ChatGPT. ChatGPT signaled that Knoxville was not just a reasonable location to complete a 50-mile birthday walk, but an ideal one. It heaped praise on Knoxville's greenways, green spaces and of course us for choosing Knoxville. With the scene set, it asked if we wanted it to generate a route we could follow. Yes, please. It provided official-looking GPS coordinates, and when asked, it created an XML-based GPX file we could import into Google My Maps to visualize the route.

This is where things went off the rails. The GPX file had no actual routing data — just a series of random-looking straight lines between points.

We pressed ChatGPT, which sheepishly admitted the file wasn't much use. But it promised it could do better. Around and around we went, failure after failure — like a GPS that confidently calls out a turn, then immediately announces it's recalculating. We should have taken the hint sooner.

The fundamental issue, I suspect, is that ChatGPT has no routing engine. It knows quite a bit about Knoxville, but it doesn't know the street-level details needed to compute an actual walking route the way Google Maps does. Its general knowledge was enough to promise us the world — but without a routing engine, it was never going to deliver.

Existing Tools: Close, But Not Quite

Next up, we explored Google's My Maps. This tool lets you create your own Google Map and, unlike ChatGPT, it actually computes walking routes. Real promise.

My Maps tripped us up in two ways. First, its drag-to-adjust routing is a great feature for casual use — but for the kind of careful, iterative planning we were doing, it became a liability. One errant mouse click or screen tap and a carefully built route would shift. Control-Z helped, but it made the whole process feel precarious.

Second, My Maps buries the route's total distance under several clicks. For most users that's fine. For us, checking distance was something we did constantly — a couple of miles either way could make or break the whole route. Having to dig for it every time wore thin quickly.

We tried sites like onthegomap.com, which shows distance prominently and makes route creation easy. But once a route was set, it was fixed — no way to go back and tune it. Perfect for mapping out a run; not quite right for planning three days of walking that needed to hit an exact distance target.

These are genuinely good tools. They just aren't built for our use case: a route that would be revised dozens of times, with distance and route shape constantly being reconsidered.

Rolling Our Own: geoassist

Ultimately, I decided to build my own tool. I give you: geoassist.

geoassist is a Unix-style script that takes in a plain-text route file and generates any number of outputs — some useful for quick planning previews (distance, a rough JPG), others for detailed navigation (GPX, KML). Under the hood it uses OpenRouteService — a real routing engine — to compute actual walking paths between your points. A route file consists of three entry types:

• Waypoints — primary established points you plan to route through. These entries start with an X, as in X marks the spot.
• Routing Hints — points fed to the routing engine to enforce a specific path, but invisible in the final map. These entries start with a V, which you can think of as an arrow into the Earth saying go here.
• Points of Interest — off-route points you may or may not end up visiting, like a Dunkin' Donuts. These entries start with a @, as in where is this business 'at'?

A point can be a latitude/longitude pair or a plain address. You can give a point a label by appending # label text.

Here's the route file for day 1 of the trip:

X SpringHill Suites by Marriott Knoxville at Turkey Creek, Turkey Drive, Knoxville, TN # SpringHill Turkey Creek

# Concord Park
X 35.86069620962343, -84.13600339974661 # Concord Park
V 35.86093969069506, -84.13496272359271
V 35.86261479769068, -84.12830087899738

X 35.874780833187806, -84.09541418622682 # Dunkin
X 35.89377609396486, -84.06858403222535 # Donato's Pizza
X 35.92390020189228, -84.03230975977412 # Food City

X Courtyard by Marriott Knoxville West/Bearden, Brookview Centre Way, Knoxville, TN # Marriott Bearden

We're starting at the SpringHill Suites, making our way to Concord Park, hitting a few resupply stops, and finishing at the Courtyard by Marriott. The routing hints steer the route through specific trails inside Concord Park that the routing engine would have skipped.

Here's what that looks like in practice:

  # Preview
  $ geoassist -a distance -f day1.pois
  17.049
  $ geoassist -a export -t image -f day1.pois > day1.jpg

  # Detailed Route Generation
  $ geoassist -a export -t kml -f day1.pois > day1.kml
  $ geoassist -a export -t gpx -f day1.pois > day1.gpx

Slow Is a Feature

The workflow for creating the route wasn't glamorous: I sat next to Shira with the file open in emacs while she pored over Google Maps. She'd pass me coordinates through chat; I'd update the file, run geoassist, and either generate a rough JPG preview or pass her a KML file to load into Google My Maps for a closer look.

Compared to dragging lines on a slick web interface, this felt slow. And it was. But that slowness turned out to be a feature. Because the route lived in a plain text file, we could experiment freely: comment out a segment with a #, try an alternate version in a new file, revert instantly. There were no accidental edits, no mystery undo states. The file was always exactly what we intended it to be. Every decision was deliberate.

Once our route was finalized, geoassist generated a GPX and KML file that we imported into our navigation tools of choice. I loaded the route into Backcountry Navigator on my phone; Shira used the Google My Maps version. Here's what both looked like loaded up:

Know Your Route Before You Walk It

One question that nagged at us as we planned was just how pedestrian-friendly the route would be. Sure, the routing engine computed a walking path — but could it be trusted? A "walking route" to a routing engine just means no highways. It says nothing about shoulders, sidewalks, or traffic.

I considered leaning on sidewalk datasets, but sidewalk data is notoriously incomplete and unreliable. I feared using this data would only give us a false sense of security.

After dropping into Google Street View manually on a number of occasions to check individual roads, it hit me: why can't geoassist do this for me?

The result is geoassist -a export -t streetview: an HTML preview of the route powered by embedded Google Street View images, one every half mile. Scroll through it and you're essentially walking the route from your laptop before you ever lace up your shoes.

We could see at a glance which stretches had real sidewalks, which were quiet neighborhood streets where that didn't matter, and which were the kind of busy arterial roads that would send us hunting for an alternate path. We rerouted at least one segment specifically because the Street View preview made it obvious the road had no shoulder and heavy traffic. That single catch was worth the whole exercise.

There's No Shortcut to a Quality Route

The through-line of all this: the time we spent deliberately poring over the route was time well spent. It's tempting to want to hand this off — to AI, to a slick web tool, to anything that feels faster. But the route was the walk. A bad route wouldn't have just been inconvenient; it could have derailed the entire project.

Part of why delegation is hard is that our route had to satisfy several competing constraints at once. It had to hit close to 50 miles — not 45, not 55. It had to pass bathrooms and resupply stops at the right intervals. It had to be safe to walk. And ideally, it would take us through interesting and beautiful places. A routing engine can optimize for one or two of those. Threading all of them takes experimentation and human judgment.

geoassist didn't speed up our planning. It gave us a process we could actually trust — stable, inspectable, and with a Street View sanity check built in. The walk went beautifully, and I think the route had a lot to do with that.

One more note for the technically inclined: because geoassist is command-line driven, it's trivial for an AI tool like Claude Code to run it. Unlike ChatGPT — which talks about routes but can't compute them — Claude Code could in principle call geoassist, evaluate the output, tweak the file, and iterate. This opens the door to having AI plan and optimize a route. I have yet to experiment with this, but the hard part of the process is now taken care of.

50 for 50: An Adventure Half a Century in the Making

To mark my 50th birthday, we walked 50+ miles around Knoxville, Tennessee. It was awesome! Here's 5 reasons why.

Terrain

The goal for 50-for-50 had always been simple: cover 50 miles, ending on my birthday. As we tried to figure out the logistics of how we might do this, I braced myself for a slog through uninspiring surroundings. Ultimately, we landed on Knoxville, TN to pull off this stunt. To my delight, Knoxville over-delivered.

We walked through quaint suburban neighborhoods, down historic boulevards and into a storied historic district. We hiked along remote-feeling trails and Knoxville's impressive greenway system. We experienced a bit of UT college life, enjoying the campus's impressive gardens and student-run creamery. We traveled on rural-vibes backroads, passing at least one horse farm. We passed two shuls, both with deep historic roots, multiple historic signposts and one very bubbly water treatment plant.

We passed by creeks, swamps, a pristine quarry and a sprawling lake. We crossed the mighty Tennessee river (twice!) and marveled at her bluffs. We passed palatial estates, densely packed subdivisions and a mobile home community. We passed what may be the longest driveway I've ever seen on a house, and an impressively camouflaged campground.

Wildlife sightings were limited, so the turtles, millipede and even statues of Smokey immortalizing past UT mascots were appreciated. Of course there was roadkill. We saw soaring ospreys, plenty of neighborhood robins, a few Canadian geese and one very confused juvenile woodpecker trying to peck a concrete wall.

We delighted in Dunkin's donuts, Bruster's ice cream, Whimsy's cookies and one perfectly prepared smoked salmon benedict. We even enjoyed a cup of homemade lemonade a father and two daughters were selling on their front lawn. We learned about the magic of Weigles, with their clean bathrooms and delicious hot chocolate.

We passed an impressive sculpture garden, the remarkable Strong Alley where majestic murals live side by side with sharp-edged graffiti and the beacon-like Sunsphere. We stood at the foot of the otherworldly Pier 865 sculpture and pondered why it was present in a park named 'the Cradle of Country Music.'

Sure, not all the walking was interesting. But I'd say easily 80% of it was. Go Knoxville!

History

Knoxville also delivered on the history front. We unexpectedly passed by and explored Pleasant Forest Cemetery, a historic cemetery founded in 1796. We got to pay our respects to Archibald Roane, a Continental Army soldier who was present at Cornwallis's surrender in 1781, and ultimately became Tennessee's 2nd governor. We also paid our respects to Lt. Thomas Boyd, who served at Valley Forge under George Washington.

We walked down the same street that General Longstreet's men did when they besieged the Union Army in Knoxville. We stood at the gun emplacements at Fort Dickerson, where Union soldiers defended Knoxville from this same assault.

We walked by Temple Beth El, a shul whose origin story stretches back to 1864 and the death of a single Confederate soldier. It was this death that helped form the area's Hebrew Benevolent Society, which ultimately morphed into the congregation we passed.

We passed the site of the historic Staub Theatre where a young Adolph Ochs served as its first chief usher. Ochs, a local paperboy and printer's apprentice, would go on to purchase and transform the New York Times into a national institution. Ochs' dad, Julius, was a founding member of Temple Beth El, where he officiated Jewish ceremonies.

We passed a marker noting Lizzie Crozier French's role as being instrumental in Tennessee's women's suffrage movement. Tennessee was the 36th state to ratify the 19th Amendment — the last state needed to reach the magic number. The vote was 49-47, with the deciding vote cast by 24-year-old legislator Harry Burn, who changed his vote after receiving a note from his mother urging him to "be a good boy and help Mrs. Catt." Lizzie was known as Knoxville's "silver-tongued suffragist" for her remarkable oratory. She was on the speaking circuit across the South, performing recitations to packed audiences who demanded encores — audiences who described her delivery as "a continuous, vivid picture before the hearers."

Discovery

Our walk served up a number of delightful mysteries for us to noodle over as we knocked out the miles. Some we teased out ourselves, some took the help of our on-demand tour guide, Gemini, and others took deeper research after the fact. All made the walk anything but a slog. Here are a few of our favorites. How many do you know?

What are these pink lines for?

When I asked Gemini about the random pink street markings we were seeing in a Knoxville neighborhood, I expected a hedge. Instead, it nailed it: we'd stumbled onto a Dogwood Arts Trail. Cool, but it gets even better. In 1947, author John Gunther called Knoxville "the ugliest city in America." Knoxville's response: pink paint. Starting in 1955, the city began marking Dogwood Trails — routes through featured gardens, ~90 miles across 13 neighborhoods, repainted each April with ~100 gallons of custom-blended pink.

Was President Herbert Hoover really the first civilian to break the sound barrier?

Uh, no. The marker is about Herbert Hoover the test pilot, not the president. A different Herb — and one with nerves of steel. Take the time the canopy came loose mid-flight and bashed him in the face, stunning him and blinding him with his own blood. He recovered and landed the plane safely. He may not have been a president, but he was a boss.

Why does this statue look familiar?

A nearly identical one stands at the entrance to Arlington Cemetery — four minutes from home. The statue is called "The Hiker," created in 1906 by sculptor Theo Alice Ruggles Kitson, honoring Spanish-American War veterans. In 1921, Gorham Manufacturing bought the casting rights and produced 50+ copies, now spread across 23 states — who knew statues came in editions? The name pairs well with the 50-for-50 theme. But wait, there's more: 37 of them serve as air-pollution monitors — identical statues placed in different climates, letting scientists measure environmental wear on the same source material. A twins study in bronze.

What type of bird is this, and why did we see so many of them?

Eastern Bluebirds — common on the East Coast, but a rare sight in DC. Why? From 1920 to 1970, the local population collapsed, going from as common as a robin to near-local-extinction. The culprit: House Sparrows and European Starlings, introduced in the 1800s, which outcompeted them for nesting cavities and ultimately displaced them. DC readers: a Silver Spring resident wrote to the Evening Star in 1956 about exactly this problem in his own backyard.

What's up with this woke sign, 'Unity in Diversity'?

Before women could vote, women organized. The General Federation of Women's Clubs — founded 1890 — was the national infrastructure for that organizing: at its peak, ~2 million members building libraries, fighting child labor, pushing for public health. "Unity in Diversity" was their motto, coined at the 1889 founding meeting — 130 years before it became a woke battle cry. The sign sits next to Lizzie French's marker because French founded the Ossoli Circle — Knoxville's women's civic club, est. 1885 — and personally attended the GFWC's 1889 organizing meeting as Ossoli's representative, making it the first federated women's club in the South.

Why does this street sign sound familiar?

Shira went to college in Philly, and I visited her more times than I can count. When we spotted Walnut Street in downtown Knoxville, then Locust a block over, both of us thought of her college days. I pulled out Gemini and asked what felt like a long-shot question: is there any actual connection between these Knoxville street names and Philadelphia's? I fully expected "fun coincidence, but no." Instead: "You've got a sharp eye! There actually is a connection." Charles McClung, who surveyed Knoxville's original 64 lots in 1791, had previously lived in Philadelphia — and brought the names with him. Walnut, Locust, and Church are all deliberate Philadelphia echoes. Gemini's verdict: "18th-century hometown nostalgia that became the permanent map of downtown Knoxville." Bonus: Gay Street in Knoxville is thought to be named after Gay Street in Baltimore — our neighbor to the north.

Gear MVPs

No blog post about a foot-powered adventure would be complete without a nod to the gear that made it work.

Shira's MVP: KT Tape. Over the years, Shira has been plagued with knee and ankle pain. We followed this tutorial for ankle support, and this one for knee support. And just like that, Shira had no pain at either location.

On day 2, Shira awoke with pretty severe pain at the top of her left foot. It hurt enough that she imagined it might be a stress fracture. We followed this top-of-foot pain taping guide, and the pain subsided.

How a couple of strips of well-placed tape can make such a difference is beyond me. But it worked. KT Tape takes some practice to apply, so if you're interested, try it before the big day. That said, it's awfully forgiving: my results never look as nice as the video versions, and yet they're still effective.

Ben's MVP: Shira's Mom's (z"l) 20,100 mAh battery pack. I relied on three devices for this walk: my Garmin Venu 2 Plus for real-time stats, my now-retired Galaxy S22 Ultra running Backcountry Navigator to reliably record our GPS track, and my new Galaxy S26 Ultra for photos, mile-marker voice notes, and Gemini field research. The Garmin and S22 held up fine on battery. The S26, thanks to all the photos, did not.

We inherited from Shira's Mom's estate a massive Ankur 20,100 mAh battery. Day one, I reluctantly schlepped it as a just-in-case item — heavy enough that I almost left it at the hotel on day two. I brought it anyway. When my phone hit 33% around 10am, I knew I was in trouble. That's when I grabbed Mom's powerbank. As luck would have it, the shorts I was wearing had a cell-phone pocket that fit the battery perfectly. I dropped it in, ran a cable to my phone in the front pocket, and charged on the go.

For the remainder of the walk, I kept my phone charged and smiled as I got to bring Shira's Mom along on our walk in an unexpected way.

The Why

As we ticked off the miles, I mulled over why we were even doing this. No doubt, the idea had its roots in my ego. I wanted my 50th birthday marked by a physical accomplishment. However, as we neared completion of the route it occurred to me that our undertaking had morphed into far more than a show of strength. We'd spent significant time planning our route, tuning gear and food lists. We breezed through some parts of the walk, while other parts were a challenge. We had the joy of discovery and moments of perfect timing, interspersed with pain and the hint of failure. Ultimately, we crushed our goal (52 miles!), even finishing on speaking terms.

In short, I'd given myself the gift of adventure. More than that, it was a right-sized adventure. This was a real challenge, with real payout, all without turning into a burden.

Hovering in the back of my mind since we committed to the 50-for-50 were two simple questions: was it going to be worth it? And was this the desperate act of an aging man? Was it worth it? Absolutely. A desperate act? Not even close. Thanks to all Knoxville had to offer, this was the real deal, an adventure to be proud of.

Time to start planning 60-for-60!

I captured a selfie and some voice notes at each mile marker. Find these field notes here.

50 for 50 - Notes From The Field

To mark my 50th birthday, Shira and I walked 50 miles in Knoxville, Tennessee. A full blog post is on my TODO list, but here are the notes I captured at every mile marker. We had a blast and it was the perfect way to mark this milestone. It goes without say, but Shira's amazing for playing along with this craziness.

Mile 0 — Departure

Day 1  ·  6:06 AM  ·  35.90394, -84.15015 ↗

• Left the hotel in the dark, chilly and beautiful
• Ben had hot chocolate in hand
• Triple navigation redundancy: Shira on Backcountry Navigator, Ben on a second phone running Backcountry Navigator, plus Ben's GPS watch
• Officially "off and running"

Mile 1

Day 1  ·  6:28 AM  ·  35.89720, -84.15615 ↗

• Pre-dawn, still dark, cool and slightly humid — quite nice
• Birds just starting to chirp; walking on sidewalk
• Suburban HOA-style neighborhood, but the empty streets and birdsong made it feel green and natural
• Small routing glitch at the very start, quickly resolved

Mile 2

Day 1  ·  6:47 AM  ·  35.88684, -84.15025 ↗

• Main road with stores — suburban Brighton / Rochester, NY vibe
• First unofficial green space: a trail-like cut-through (not a designated path, but a welcome break from road walking)
• First encounter with Turkey Creek — worth tracking as a recurring landmark

Mile 3

Day 1  ·  7:12 AM  ·  35.87799, -84.14841 ↗

• Overcast morning, sun just starting to come up; wide quiet road
• Spotted a historic marker for Pleasant Forest Cemetery — fell directly on the route, no detour needed
• Found the grave of an early Tennessee governor / frontier judge (late 1700s / early 1800s; name to look up) — described as "an absolute gem of a find"
• Lesson noted: add historic cemeteries to future route waypoints; same logic applies to public gardens

Mile 4

Day 1  ·  7:31 AM  ·  35.86465, -84.14289 ↗

• Pleasant downhill stretch on a wide sidewalk, approaching Concord Park
• ChatGPT had recommended Knoxville over Washington D.C. for this walk, calling it a "sleeper hit" for greenways — verdict at mile 4: correct
• Printed UTM pocket map paired with GPS device is working as hoped

Mile 5

Day 1  ·  7:57 AM  ·  35.86131, -84.13497 ↗

• ~8am, overcast
• First obstacle: a bridge with no sidewalk — short and manageable; Tennessee drivers gave a friendly finger wave
• First views of Fort Loudoun Lake — overcast, some fog, calm and beautiful
• Wildlife: several Canadian geese and one blue heron
• Entered Concord Park: trail system felt like true wilderness despite the park's size — highlight of this leg
• First ProBar Meal Bar (chocolate chip peanut butter, ~400 cal): delicious
• Note: KT-taped Shira's knees and ankles the night before — will evaluate effectiveness at end of journey

Mile 6

Day 1  ·  8:22 AM  ·  35.86347, -84.12054 ↗

• Concord Park rated 10/10 — real green space, legit trail, felt like genuine wilderness; some car noise audible but visually excellent
• Unexpectedly passed a historic cemetery along the route
• Current stretch: narrow road, no sidewalk, minimal shoulder — a bit sketchy, but no regrets given the overall experience
• Aside: recently migrated to Samsung Galaxy S26 Ultra; migration fast; cameras and speed noticeably better; one outstanding issue — Bluetooth shutter on the JJ02 tripod not yet paired

Mile 7

Day 1  ·  8:43 AM  ·  35.87041, -84.10577 ↗

• Busy road with no sidewalk or shoulder; must step into grass when cars pass — "luck has officially run out" for infrastructure
• Setting is suburban but feels almost rural: very large lawns, large homes, lots of green, a pond/lake inlet — quite beautiful, would be ideal with a path
• Dunkin' Donuts less than half a mile ahead — first tagged restaurant on the route

Mile 8 — Dunkin' Donuts

Day 1  ·  9:35 AM  ·  35.87753, -84.09348 ↗

• GPS ticked to 8.0 miles while seated inside Dunkin' — counts anyway
• Ben: everything bagel (good, needed more toasting, needed lox)
• Shira: avocado toast with egg ("good enough"); egg described as the weirdest-looking egg Ben has ever seen
• Departed with 25 munchkins and a Cream Supreme donut
• Tables had outlets; devices charged; logistics "dead on perfect"

Mile 9

Day 1  ·  9:55 AM  ·  35.88601, -84.08034 ↗

• Left Dunkin'; brief sketchy intersection, then full sidewalks
• Passing A.L. Lotz Elementary School
• Temperature: 62°F around 10am — much cooler than anticipated; taking the win
• Supreme Cream Donut verdict: fantastic; wedding cake munchkins: delicious
• Hot chocolate at the hotel > tea: still hot, has calories, no diuretic effect (fewer bathroom needs on a route with few facilities)
• Notable exchange: passed a house flying a pink "It's a Girl" flag instead of an American flag. Ben: "charming old-fashioned way to announce a new baby." Shira: "You're just announcing to the world there's a baby to kidnap." — a perfect encapsulation of the Ben-vs-Shira worldview gap

Mile 10

Day 1  ·  10:17 AM  ·  35.89306, -84.06793 ↗

• One-fifth of the project complete — significant on any day
• Sidewalks throughout; passed palatial mansions and more clustered subdivisions; "easy breezy" mile
• Both wearing matching blue sun hoodies — unintentional but noted as potentially adorable
• Approaching a fork: left toward stores (and a restroom) or right to continue the adventure

Mile 11

Day 1  ·  10:43 AM  ·  35.88966, -84.05811 ↗

• Quiet residential neighborhood: large lots, mature trees, temperature warming up
• Donato's Pizza waypoint arrived before opening hours; Shira spotted a K-Brew adjacent — first visit; very nice, clean, large space
• Ben skipped the cheesy jalapeño bagel — long line formed while in the bathroom; they left impatient
• Time ~10:40am; sun beginning to peek through clouds

Mile 12

Day 1  ·  11:12 AM  ·  35.89861, -84.04718 ↗

• Transitioned from neighborhood to a country two-lane road: no shoulder, some traffic — a bit sketchy but scenic with lots of green space
• Some elevation gain — notable since the trip hasn't had much
• Shira scolded Ben for looking at a notebook while on a shoulderless road
• Next: mile 13, "the bar mitzvah mile marker"

Mile 13

Day 1  ·  11:41 AM  ·  35.90971, -84.04222 ↗

• Back on neighborhood roads after a stretch of busy road; safe but required attention
• Weather: overcast, slightly warmed, less humid — good walking conditions
• Stopped to tape two of Shira's blisters
• Spotted cactuses used as yard decorations — a surprise in Tennessee
• Street View route preview (HTML with Google Street View at every half-mile, generated during planning) paid off: gave real confidence about which segments were safe before they arrived
• Shira primarily using the waypoint distance table on the pocket map rather than the map itself; Ben using the UTM grid for broad position
• Limitation noted: the pocket map's scale is useless for micro-navigation at junctions — not enough detail to decide left vs. right in the moment

Mile 14

Day 1  ·  12:03 PM  ·  35.91953, -84.03197 ↗

• Weather improving: clouds parting, blue sky, large white fluffy clouds — "a very nice moment"
• Found a larger road with a sidewalk; next major stop: Food City
• Lemonade stand: dad with daughter and son selling from their front lawn; bought a pint of pink lemonade — delicious
• One member of the group officially announced feet hurting

Mile 15

Day 1  ·  12:39 PM  ·  35.92576, -84.03424 ↗

• Missed the mile 15 check-in and selfie during a foot care stop at Food City — got distracted and walked straight through without noticing
• Mile 16 note covers both miles

Mile 16

Day 1  ·  1:12 PM  ·  35.93491, -84.03043 ↗

• Hit mile 16 post-Food City; Shira's feet "definitely cooked"
• Concern is more about tomorrow than finishing today
• Took ibuprofen at Food City as preventative
• Sun shining, blue sky, white clouds, walking on sidewalk through residential neighborhood with lots of trees — "a perfect moment"
• Recovery plan for the evening: feet up on wall 15–20 min (tip from Shira's co-worker), protein-heavy food, charge all devices
• ~2.5 miles remaining for the day

Mile 17

Day 1  ·  1:31 PM  ·  35.93264, -84.01825 ↗

• Noticed pink painted arrows and lines on the road; asked Gemini about them
• Gemini identified it immediately as the Knoxville Dogwood Arts Festival trail — a marked neighborhood route through areas with notable dogwood gardens
• Impressed by Gemini's ability to identify the markings from just two data points (city + color)
• Under a mile from the hotel; debating whether to stop for lunch first
• Figured out why mile 15 had no check-in: Ben got distracted on his phone and they walked through without noticing — the walk still demands real attention

Mile 18 — Whole Foods

Day 1  ·  2:18 PM  ·  35.93621, -84.00787 ↗

• Shira made the call to stop at Whole Foods despite being under a mile from the hotel — Ben calls it a great decision
• Shira: avocado and spicy tuna sushi; Ben: salmon, tuna, and avocado sushi plus two more donuts and a fancy electrolyte lemonade
• "18 miles, as in chai, as in life"
• Recorded at 2:07pm
• Final stretch to hotel: access road with no shoulder, navigating carefully

Mile 19 — Arrival

Day 1

• Reached the hotel and completed the day
• Car had been staged there the night before; laptop left in the car overnight — no issues
• Physical status: both feeling good; ibuprofen from Food City has kicked in
• Shira: "I feel great. I feel much better."
• Day reflections: "This feels like a really wonderful way to celebrate 50"
• The mile-by-mile updates and photos gave the day a rhythm and made it feel like it moved quickly

Mile 20

Day 2  ·  5:23 PM  ·  35.93442, -83.99770 ↗

• 6:28am, April 27 — the day before Ben's birthday
• Low 60s, chilly; wide sidewalk past closed retail strip (Nothing Bundt Cakes, Goodwill, Aldi) — empty and peaceful
• Both feeling better than expected after yesterday's 19 miles
• Recovery credit: legs elevated the night before, KT tape on knees and ankles, ibuprofen (used carefully), and baseline fitness
• Spotted a historical plaque for Herb Hoover (1912–1952), test pilot — first civilian to break the sound barrier (NOT Herbert Hoover the president — important distinction clarified at mile 21)

Mile 21 — Kingston Pike

Day 2

• On Kingston Pike heading toward Knoxville
• Breakfast: ProBar protein bar, cookie dough flavor — surprisingly good; adding to hiking food repertoire
• Working through the ~25 donut holes from Dunkin' the day before
• Duck Donuts near the hotel was closed; Krispy Kreme was in the wrong direction — skipped
• Backpack weight: 9 lbs — mostly food and drink (one water bottle, one Gatorade), plus foot supplies and first aid
• Route is a figure eight: two nights at one hotel, no need to carry clothes or extra supplies — significantly reduced pack weight

Mile 22 — Kingston Pike

Day 2

• Kingston Pike: grand, long-established homes with generous lawns — "Brighton Esplanade vibes"
• Passed Heska Amunah synagogue (Conservative, chartered 1890) — one of the first clear signs of Jewish presence in Knoxville on the walk; also noticed a kosher section at a supermarket earlier
• Breakfast report: Shira tried a True bar (peanut butter & jelly, 12g fiber) — took the smallest bite and declared "it wasn't food." The day was saved by a Nature Valley Crunch peanut butter granola bar: "exactly what a mom would pack in a lunchbox"
• Temperature 55°F, sun out, bright blue sky — first real sunny day
• First sunscreen and hats deployed

Mile 23 — University of Tennessee area

Day 2

• Standing at Tyson Place (formerly Tyson Junior High) across from the University of Tennessee — facade reminiscent of Brighton Middle School
• Kingston Pike highlights: - Temple Beth-El (Reform synagogue, roots to the 1860s; began as a burial coordination association) - Bleak House / Confederate Hall — Longstreet's base during the Confederate siege of Knoxville; the Union held the city despite it being in a Confederate state - Ossoli Circle — Lizzie Crozier French founded it in 1885; carries a GFWC "Unity in Diversity" sign
• Reflection: had they taken only greenways today, they would have missed all of Kingston Pike's history — urban corridors carry their own rewards

Mile 24 — Under the UT Bridge

Day 2

• Walking under a University of Tennessee pedestrian bridge; urban / university-town feel
• Pit stop: McDonald's — hash brown described as very good; bathrooms less so (college-town McDonald's)
• Observation on kiosk ordering: both McDonald's and Dunkin' now kiosk- first; Ben notes the cognitive dissonance of wanting to talk to the person standing right there
• Looking forward to historic downtown Knoxville ahead

Mile 25 — Halfway / Downtown Knoxville

Day 2

• Mile 25 of 50 — officially halfway
• Stopped at the sculpture garden outside the Knoxville Museum of Art; noted a piece: /Motor City/ by Charles Pilkey — gears, miniatures, and figures, worth extended viewing
• Sun Sphere (1982 World's Fair): arrived too early to go up inside; photographed from outside. Ben notes 1982 feels both very old and very recent for a World's Fair
• Walked through UT campus; stopped at four historic signs (to Shira's dismay) - A Marine general with Tennessee connections buried at Arlington — Ben wants to find the grave - UT predates the Civil War; Union and Confederate forces both took control of "the Hill" fortification; Longstreet's headquarters visible
• Knoxville utility box art: vinyl-print paintings, each highlighting a local artist alongside their work — smart use of infrastructure
• Fort Dickerson listed as upcoming stop; Ben is excited about it
• Heading to Market Square

Mile 26 — Downtown Knoxville

Day 2

• Market Square: spotted a zero mile marker placed by the AAA club (purpose to research)
• Strong Alley: professional murals and renegade graffiti coexist side by side — a standout surprise
• Cradle of Country Music Park: modern/abstract sculpture, incongruously unrelated to country music
• Gay Street: shops all closed (too early), but crossed the Gay Street Bridge — Tennessee River described as "majestic"; perfect temperature, almost no other walkers
• Old courthouse: found "The Hiker," a statue honoring Spanish-American War veterans — the same statue appears at Arlington Cemetery
• Adolph Ochs monument: started as a Knoxville paperboy before becoming publisher of the New York Times; his father was a founding member of Temple Beth-El (passed at mile 23) — a satisfying web of connections
• Heading to Fort Dickerson next

Mile 27 — Kern's Bakery / Leaving Downtown

Day 2

• Stopped at Eggs Cetera inside Kern's Bakery (originally an industrial bread factory, now a food court)
• Ben: eggs benedict with smoked salmon on a croissant — outstanding; minor quibble that the croissant didn't hold up under the lox
• Shira: eggs benedict with avocado — described as flawless, perfectly poached eggs
• Notable contrast to yesterday's Dunkin' egg "from a comic book"
• Spotted a Rotary Club sculpture near the museum: a man on a globe holding a child and a needle — honoring work vaccinating children against polio in the 1990s. Observation: a monument that was once unambiguously triumphant now carries an unintended political charge given the current moment
• Crossed back over the bridge; now through a regular residential neighborhood heading to Fort Dickerson

Mile 28 — Fort Dickerson (entering)

Day 2

• Arrived at Fort Dickerson Park — stopped to shed layers and apply sunscreen
• Monday: have the park essentially to themselves
• Came off a neighborhood road and immediately entered real forest — felt like a genuine transition to wilderness in short order
• Shout-out to red Gatorade: amid high-tech hydration options, classic red Gatorade just works
• Mountain biking trails visible; must be a popular MTB destination
• Ijams Nature Center (318-acre urban greenspace, 14+ miles of natural- surface trails) is the more premier wilderness option nearby, but Fort Dickerson fit the route perfectly and exceeded expectations
• Approaching Civil War earthworks

Mile 29 — Fort Dickerson (the fort)

Day 2

• Fort Dickerson: Union-held earthworks fort, key to defending Knoxville during the Civil War
• The fort's value was largely deterrence — well-constructed and well-sited on high ground; signaled to Confederate forces that taking it would cost too much
• Reminds Ben of Fort C.F. Smith in Washington D.C. — both are earthworks (mounds of dirt at this point), requiring imagination to appreciate; contrasts with masonry forts like the one in Puerto Rico, which are immediately awe-inspiring
• The park exceeded expectations: downtown → impressive green space → history, all in close proximity
• Weather: 75°F, 59% humidity, sunny with blue skies and light clouds
• Next: head to the quarry viewpoint, then cross back over the bridge

Mile 30 — Fort Dickerson Quarry

Day 2

• Still within Fort Dickerson Park, now circling the quarry
• Water: emerald colored, steep and sharp quarry walls — striking
• Gear spotlight: - Shira's Camelbak insulated water bottle: keeps water cold → she drinks more; bite-suck valve preferred for trail use - Large Anker battery pack from Shira's mother's estate (z"l) — finding it was a surprise; Ben notes it brings extra joy, a way to carry his mother-in-law with him on the adventure
• Phone management: heavy photo and voice memo use drained it to 33% by ~11am; the Anker is the solution
• On the horizon: University of Tennessee Creamery

Mile 31 — Crossing Back Over the Tennessee River

Day 2

• Leaving Fort Dickerson, crossing back over the Tennessee River
• Sunny, clear; back on solid concrete after the park — easier walking
• Views of the Gay Street Bridge and Sun Sphere visible in the distance
• Wildlife: an osprey flew near a group of pigeons — every pigeon immediately scattered
• Reflection on Knoxville vs. Washington D.C.: Knoxville delivered on murals, Civil War history, green space, beautiful views, and great weather; the novelty factor (everything unfamiliar) made it a genuine adventure. D.C. would have been more introspective. Knoxville = outward discovery; D.C. = inward reflection. Floats idea of a future D.C. walk

Mile 32 — Volunteer Landing

Day 2

• Beautiful spot by the river; Three River Rambler train on display nearby
• Historical plaques line the landing (Ben was reading slowly until Shira noted the Creamery closes at 7pm)
• Clean public bathrooms — appreciated
• Gemini query about the street grid: both Ben and Shira independently thought of Philadelphia when they crossed Walnut St. — Shira attended UPenn. Gemini confirmed: Charles McClung (1761–), originally from Lancaster then Philadelphia, laid out Knoxville's streets and explicitly modeled them on Philadelphia's grid, choosing Walnut, Church, and Locust to evoke his hometown. Genuine delight at an unexpected historical connection
• Next: gardens, then the Creamery (~3 miles)

Mile 33 — Neyland Greenway

Day 2

• Walking along the Tennessee River
• Believe this is the first greenway on the entire 50-for-50 route
• Neyland Greenway (N-E-Y-L-A-N-D) — Shira's initial take: "I think it's just a sidewalk." Confirmed it is legitimately a trail
• River: calm, flat, wide, inviting; across the water: River Bluff Wildlife Area — bluffs described as "really, really picturesque, very beautiful"
• Trail mostly to themselves; a couple of bikers passing

Mile 34 — UT Gardens / College of Veterinary Medicine

Day 2

• Selfie in front of a UT campus building near the College of Veterinary Medicine; building has suspiciously tall and narrow loading doors — presumably for moving large animals
• UT Gardens: a major hit; significantly slowed the pace but worth it; many things in full bloom
• Kitchen garden: impressive display of fruits and vegetables actively being grown
• Standout plants: a poppy (caught the eye; identified via Google) and an entire hardy hibiscus breeding bed — apparently a research project on varieties suitable for home gardeners across different climates
• Heading to the Creamery next

Mile 35 — UT Creamery

Day 2

• Long-anticipated stop; hope was high quality ice cream, open when they arrived — both delivered
• Ben: two large scoops, chocolate and vanilla
• Shira: one very large scoop of peanut butter
• "Outstanding" — ate every bit, no regrets
• 4.5 miles remaining to hotel; skies mostly cloudy, sun diffused — "really pleasant"
• Turned onto a legitimate forested greenway — a real path, not just a labeled sidewalk

Mile 36 — Third River Greenway

Day 2

• Now on the Third River Greenway: wide, paved, tree-lined — the greenway hype paying off
• Shira is physically worn down; pain management is the focus: tracking when the next ibuprofen dose is allowed
• Shira declared it ibuprofen time at the end of the recording

Mile 37 — Greenway Home Stretch

Day 2

• Wide, wooded greenway; sun out, blue sky — the greenery really pops
• Shira waiting for ibuprofen to kick in
• Reflection on the deeper why of the trip: - Most obvious: mark his 50th birthday with something notable rather than letting it pass quietly - Deeper: gave himself the gift of an adventure — the preparation itself (routing tools, routing strategies, gear and food planning) was part of the gift - Discoveries hoped for: UT Creamery, Fort Dickerson green space ✓ - Unexpected discoveries: historic cemeteries, Strong Alley murals - Verdict: "It has overly succeeded so far"

Mile 38 — Whimsical Cookie Company

Day 2

• Just left the Whimsical Cookie Company (tagline: "cookies fix everything")
• Got gooey chocolate and gooey lemon cookies — highly recommended
• Notable debate: one cookie had "happy birthday" written on it, but Ben refused to eat it — his birthday is tomorrow, not today
• Back on Kingston Pike (the same road the day started on); much busier now with traffic
• Plan: duck off onto a greenway soon

Mile 39 — Nearly Back

Day 2

• Nearly back at the hotel
• Route summary for Day 2: Kingston Pike outbound, downtown Knoxville, Gay Street Bridge, Kern's Bakery, Fort Dickerson, UT Gardens and Creamery, Neyland Greenway, Third River Greenway home
• Final greenway stretch: unexpectedly pleasant and wide, away from traffic
• Passed a bonus cemetery but did not stop
• Overall assessment: "a route that had it all" — sunrise, history, architecture, downtown, a bridge, food, real trail hiking, a university, and greenways
• Heading to hotel to recover before mile 40

Mile 40 — Rain Delay and Foot Care

Day 3

• Heavy rain started at 4:39 AM; cleared ~30 min before the 8:59 AM start
• Intentional late start to wait out the storm; umbrellas packed just in case
• Extensive foot prep: tape, blister pads, Gurney Goo (recommended by an adventure runner to prevent blisters and protect against wet feet), KT tape on Shira's legs ("looks like a KT Tape commercial")
• Shira researched and applied box-style shoe relacing to reduce constriction
• Breakfast: tortilla with peanut butter and chocolate chips; Nature Valley peanut butter granola bars

Mile 41 — Forest Side Roads

Day 3

• Sky gray but holding; possible rain in ~30 min from a passing storm
• Started from hotel on a main road → sidewalk → narrow side road through a wonderful forest → approaching another main road with no sidewalk
• Ibuprofen clearly helping; feeling strong out of the gate; first mile flew by

Mile 42 — Data-Driven Field Report

Day 3

• Found a sidewalk ~200 yards onto the main road — relief
• Creeks nearly overflowing from overnight rain
• Passed two rehab centers, a surgery center, and a senior living complex — running joke about potential future stops
• Ibuprofen and KT Tape in full effect; considering a Tylenol booster
• Trail mix of the day: peanuts, chocolate chips, and pretzels — simple "Boy Scout gorp" outperforms fancy superfood options in practice
• Main idea captured: a "data-driven field report" blog post assembled from mile-marker selfies, voice memos, and GPX files, built with Claude Code tooling during the rain delay — a permalink to share for birthday well-wishes; a narrative post will follow once rested

Mile 43 — True Liberty Ice Packs

Day 3

• Continuing down Middlebrook Pike — wide road, good sidewalk
• Passing subdivisions, office parks, closed sushi restaurant, liquor stores
• Sky overcast, chilly, but dry; bodies still feeling good
• Gear shoutout: True Liberty odor-proof bags (thick, like oven cooking bags) used as improvised ice packs for end-of-day recovery — don't leak as ice melts, easy to reseal with the included ties, reusable across nights
• Shira noted that dictating voice memos while walking downhill is a "missed opportunity in performance" — pace slows when talking

Mile 44 — Middlebrook Pike / Weigel's Hot Chocolate

Day 3

• Still on Middlebrook Pike; good sidewalk, sky starting to clear
• Walked past a stretch of election yard signs (Knox County races)
• Stop at Weigel's convenience store: got a hot chocolate — delicious
• Hot chocolate + cool breeze + sidewalk + 44 miles = everything pointing in the right direction

Mile 45 — Backcountry Navigator App Review

Day 3

• Still on Middlebrook Pike; clouds clearing, still a little chilly
• Shout-out to Backcountry Navigator (Android): an old app nearly dropped in favor of something newer, but it earned its keep on this trip - Cleanly imports the custom GPX route files - Old S22 Ultra (replaced ~1.5 weeks ago) repurposed as a dedicated tracker: in the backpack, airplane mode, recording the walked track - More reliable than the Garmin Venue 2 watch, which needed restarting a couple of times
• Best for: nuts-and-bolts navigation, no extraneous features

Mile 46 — Brewster's Ice Cream

Day 3

• Now off Middlebrook Pike, on Cedar Bluff Road; 4 miles to the 50-mile mark
• Arrived at Brewster's Ice Cream at 11:01 AM — one minute after opening
• Lone high school-age clerk visibly confused by walkers wanting ice cream at 11 AM on a chilly day
• Ice cream described as "absolutely delicious"; sun briefly peaked out during the stop

Mile 47 — Sunshine and Bluebirds

Day 3

• One mile past Brewster's — confirmed as the exact halfway point of the walk
• On narrow rural/suburban back roads; sun finally out, mostly blue sky
• First time removing the long-sleeve shirt; switched to t-shirt, applied sunscreen for the first time all trip
• Wildlife reflection: landscape feels like Virginia with some upstate NY character; common birds (robins, blue jays, cardinals) feel familiar, but eastern bluebirds appear here as casually as robins do back home — visually striking and a trip highlight

Mile 48 — Backpack Gear Review

Day 3

• Mile 48 of 50; sun out, blue sky, puffy clouds — "conditions could not be more perfect"
• Shira's pack: Osprey Tempest 20 — highly recommended; small size limits overpacking, many pockets, vented back panel, hip belt with pockets, very comfortable for high-mileage days
• Ben's pack: standard navy Jansport school backpack — functional and low-profile (looks like any everyday bag), Cordura fabric, side water bottle holder; no hip belt or back padding; items shift and press into the back (Gatorade bottle migration noted); wouldn't broadly recommend for long-mileage use but Ben acknowledges some stubbornness in choosing simplicity over features

Mile 49 — Gemini as Instant Tour Guide

Day 3

• Finishing a two-lane, no-sidewalk suburban/rural road; 67°F, blue sky, puffy clouds — perfect walking weather
• Passed mobile home community, packed subdivision, and homes on enormous lots — notable diversity in housing scale
• Gemini as ad hoc tour guide: used periodically throughout the walk; highlights include the Knoxville street grid / Philadelphia connection and identifying "Bob Kirby" and another local name at a landmark
• Tradeoff: picking up your phone risks missing something in the moment; works best during quieter stretches
• Passed many Kim Frazier for Mayor signs; looked her up via Gemini — "sounds pretty good" with the caveat it's just an AI summary
• One more mile to go

Mile 50 — We Did It

Day 3

• Mile 50 dedicated to Shira — partner of 28 years; grateful not just for this trip but for making all adventures possible; specifically thanks her for walking every step rather than waiting at the finish
• Good omen: spotted a killdeer — common bird but Ben has never seen one before; struck by its distinctive pattern; takes it as a sign there are still new things to discover at 50
• Trying ibuprofen + Tylenol combination for pain management
• Hitting mile 50 doesn't mean the walk is over — hotel is a couple miles further; committed to walking the whole way (completist nature)

Mile 51 — Bonus Mile / Grit

Day 3

• Pace: 18–19 minutes per mile — "blazingly fast" given the accumulated mileage
• Shira recognized the terrain near the finish, signaling they were almost done
• Ben's word for the entire 50-for-50 journey: *grit*
• Shira described as a "rock star" throughout the project

Mile 52 — Finish / Lessons Learned

Day 3

• Finished in the hotel parking lot, ~10–20 yards from the entrance
• Final stretch: main streets with sidewalks → major bridge (no sidewalk but very wide shoulder) → Turkey Creek Greenway (shaded, wilderness-feel, top-notch) — a great way to finish

The Route

Day 1

Day 2

Day 3

Day	Planned	Completed
Day 1	GPX  KML  Street View ↗  Map ↗	GPX
Day 2	GPX  KML  Street View ↗  Map ↗	GPX
Day 3	GPX  KML  Street View ↗  Map ↗	GPX