This past Saturday, I was waiting in line to use a water fountain behind a kid who was probably about ten years old. We were in Connellsville PA. Based on context clues, I presume the kid lived nearby. I had just biked about 65 miles from my front door to be there. The kid was eyeing up my bike and the group of folks I was with.

“Is it true this trail takes you all the way to Picksburg?” The kid probed, absolutely nailing a yinzer pronunciation of the city’s name in the process.

“Yessir. All the the way.” I confirmed, giving him a nod.

“Did you go there?” The kid asked with a bit of hesitation.

“I live there! We started from my house this morning and rode our bikes here.” I explained, trying to come off as upbeat as possible for this kid’s benefit.

This satisfied the kid’s curiosity, and he thanked me before getting back to the water fountain we were waiting for. I can’t help but appreciate the kid’s politeness and willingness to ask questions to get the answers he wants.

For those of you in Picksburg who are unaware, if you ride your bike on the river trails to the South Side end of the Hot Metal Bridge, you can just keep on going all the way to DC, entirely on trails following old railroad paths and safe from car traffic. Between Pittsburgh and Cumberland, Maryland, there is the 150 mile Great Allegheny Passage (or “the GAP,” as it is known colloquially) which connects in Cumberland to the C&O Canal Towpath. This trail, which is far more spartan than the GAP, will take you the next 180 or so miles to Washington DC. This is an absolutely unappreciated gem as far as infrastructure goes, and I have learned that it is a lot more accessible than many people realize. In conversations I’ve had over the years with people, both cyclists and non-cyclists alike, it seems like a lot of people vaguely know that there is “a trail that takes you all the way to DC” (as it is often described in questions people ask me,) but people seem to not fully comprehend exactly how well-defined, complete, and easy to navigate this route is.

If you like views like this, definitely consider making this trip. It’s like this for most of the way.

And so, this past Saturday, I set off on a five day trip to get to DC from Pittsburgh on bikes along with my father-in-law Tim and our mutual friend Jackie. Both are very competent cyclists and we’ve gone on several bike trips together over the last few years. Both are also very easy to get along with, which is an exceedingly important quality to consider when choosing people to spend the better part of a week constantly in close proximity of. The three of us did RAGBRAI last year together, in which we rode 500+ miles across the state of Iowa over the course of a week in absolutely disgusting conditions: Absurd humidity, multiple days where the temperature was over 100 degrees, long stretches of direct sun with no shade, overcrowded campsites, long lines, the works. If we could stay friendly with each other after that, I assume we could ride together in anything.

This isn’t the first time I’ve made the Pittsburgh to DC bike trip. I made one failed attempt in the opposite direction (DC to Pittsburgh) in 2013 in which I got absolutely rained out about 85 miles in. Excessive rain on the C&O turns the trail to mud with a peanut-butter like consistency, so on the very first day of that trip I found myself sinking into the trail more than traveling over it. I hadn’t given myself enough time to deal with such setbacks, so my absolute treasure of a wife came and rescued me from someplace in Maryland. Looking back, it’s probably for the better that I didn’t continue, as I clearly had no idea what I was doing.

In 2021, I revisited this trip with three friends and we went from Pittsburgh to DC with little issue. I definitely overpacked for that trip and worried a lot more about preparedness than a trip like this warrants. After my prematurely-aborted attempt eight years prior, I erred on the side of over-preparation. I brought enough clothes to last a week, multiple battery packs, an entire-ass spare chain, six spare tubes, and I even brought two pairs of bike shoes. My bike had to have weighed over 100 pounds by the time I got on it. Despite my over-preparation I still managed to bonk out on the second to last day from lack of nutrition. In retrospect, I clearly still had no idea what I was doing.

I’m not sure what kind of hooligan would deface property with a GIVE UP sticker, but I saw many of them along the way.

Since that trip in 2021, I’ve done a lot more biking and grown as a cyclist. I started a bike club with the friends who went on that trip with me, and it’s grown to a size we never considered possible. As we’ve grown as a club, we have attracted new people who I have learned a ton from over the last few years, and as the club has grown adventurous I’ve worked to keep up with them. When the hills didn’t seem to satisfy the club, we found bigger hills to go up together. When the rides didn’t seem long enough, we went further. People want to bike in the snow over the winter? We’re doing it together. Leading several group rides per week has also forced me to learn how to remain calm in the face of adversity: when you’re in charge and somebody breaks down mid-ride, you’ve got to learn to be part of the solution and not one of the people freaking out about it.

So when it came to planning this trip from Pittsburgh to DC, I have to admit that I did very little planning at all. I booked an AirBnB a couple months prior for the first night of our trip just to anchor myself into actually doing the trip. Plans are great, but until there’s money tied up in reservations, I’m liable to prioritize other things when it comes time to start pedaling. Aside from that, the only preparation I did was changing my brake pads and bar tape two days before we left. The bike I took on this trip had been in my garage since last October or so, and I hadn’t thought to do any maintenance until 48 hours before we were due to leave. Turns out, it had no brakes or bar tape. There was a brief moment where I thought “it’s a flat ride, do I even need brakes?” Don’t worry - common sense won out over laziness in the end.

The first day of our trip started out a bit precarious; Jackie had a bent derailleur hanger the night before, which she thought had been fixed before we took off. Within three miles of hitting the road, though, her derailleur was making noises that didn’t sound like it would be sustainable for 340ish miles. Thick Bikes just happened to be along our route for the morning, so we made a pit stop. I would like to take a moment to appreciate that by the time we stepped foot into the shop, Chris and Paul had Kona derailleur hangers up on the shop’s computer and were talking about Jackie’s derailleur. I did not call ahead. They did not know we were coming. I had mentioned in passing to Chris the night before that Jackie was having issues and as soon as he saw us in the parking lot he scrambled to get a solution together.

Please consider this my reminder - a plea even - please buy your bikes and bike parts at a locally owned shop. Let them be the people to service your bikes. Make relationships with them. Make friendships with them. They need us and we need them. It’s a beautiful thing.

Anyway, after a 20 minute stop at Thick we were back on the road. Jackie’s derailleur was not an issue for the rest of the trip. We continued on our way and made it to the nicest AirBnB I think I’ve ever stayed in once we got to Ohiopyle. I had a couple beers and a veggie burger at the House Cafe, and the first day was in the bag, weighing in at about 80 miles total. I have to admit that the first 60 miles or so of the GAP are boring as hell to me at this point, so I didn’t spend a lot of time taking in scenery along the way. I have done so many long out-and-back rides along this trail over the past decade that I didn’t really consider this trip “started” until we got to Ohiopyle.

I don’t know why, but I love taking pictures of people taking pictures of their bikes.

The second leg of this trip had us going 70 miles to Cumberland, which completed the GAP for us. As mentioned earlier, the Pittsburgh-DC trip connects two trails: the GAP and the C&O Canal Towpath. I like to get through the GAP in two days as it is largely paved, I’ve seen most of it a ton of times, and the C&O is more likely to cause issues that require additional time for the trip. I set aside six days to do this trip, made a plan that does it in five days, and figured if we need to add a day due to bad conditions on the C&O, we’ll have that option. This worked out well in the end, as we never needed that buffer day, but it was a really nice safety net that kept us from having to worry.

The first 50 miles of the Ohiopyle to Cumberland leg of this trip are at an incline. You’re technically climbing a hill for the entire fifty miles. It’s not a steep hill, and for the most part it doesn’t feel like a hill, but it’s technically a hill. You do end up working harder, you get zero opportunities to coast while resting, and you may notice that you’re consistently going slower than you would expect by a couple miles-per-hour. These trails were built for rail lines originally, though, so there are no steep ascents or descents to worry about. Eventually you make it to the Eastern Continental Divide, the highest point of elevation you’ll encounter on this trip, and the trip is all downhill from there.

In the year 2013, before I first attempted making this trip, I bought a 2012 Surly Disc Trucker. This was the beginning of my relationship with Thick Bikes as my preferred local bike store. The Surly Disc Trucker back then was one of only a handful of bikes made specifically for long distance bike touring. I bought the bike, I bought all of the accessories, the bags, racks, Brooks saddle, all of it in anticipation of that failed attempt I made back then. I eventually got that bike to DC in 2021, and it was stolen from me shortly thereafter from the parking lot of a resort in Virginia Beach. I’ve not been back to Virginia Beach since.

A pic of my stolen Surly from the beginning of my last DC trip in 2021. Everything was much cleaner back then.

After that bike was stolen, heartbroken, I searched the internet for a replacement. I spent weeks looking at options that came close (but not close enough) to the one that I lost. This was during the peak of pandemic supply chain disruptions and the chaos that ensued, so even though I technically could afford to just buy a new 2021 model of the same bike, they were exceedingly hard to come by at that point. (Once again, shout out to Chris at Thick Bikes who told me he would call me if he got any in.) But also, I didn’t want a new one, I wanted the one I lost. I failed my first attempt at a DC trip in 2013, but I put damn near ten thousand miles on that bike across several states and assorted adventures. I considered that bike to be part of me — an extension of my person — if that doesn’t sound too cliched.

One day on Facebook Marketplace, losing hope of ever finding a suitable replacement, I found a 2012 Surly Disc Trucker. The same green as the one I lost. The same racks. Same size. In Kansas. I was prepared to drive halfway across the country to buy this bike, no question whatsoever. The asking price was quite a bit higher than it would be at any other point in history, but this was 2021 when the used bike market was absurd. I didn’t care. I needed this bike. I messaged the seller and told them that I desperately wanted that exact bike and was willing to pay for it sight unseen ASAP and travel to get it. And then I waited.

The next day, I got a reply back to the sender. I think she was a bit skeptical of my message, because buying a ten year old bike for the price of a new bike is silly enough as it is, and paying to travel across the country to pick it up is even sillier. Her initial response seemed a bit hesitant to engage, because clearly this is too good to be true and I must be a scammer, right? I explained my situation, the bike I was very attached to getting stolen, and sent a picture of my stolen bike taken at the Eastern Continental Divide. It turns out the seller of this bike was the widow of the previous owner of the bike. She had a photo of her late husband and his bike from the same point of the Eastern Continental Divide. She sent me that picture along with a few tales of her own adventures with her husband along the GAP and C&O, and told me she absolutely wanted me to have this bike. I stuck my older son in the car and we road tripped to a mid point somewhere in Indiana. I had to bribe my kid by telling him we could get all of the snacks and Dr. Pepper he wanted along the way.

When we got to the Eastern Continental Divide on this trip in 2024, I took a photo of this replacement bike and sent it to the lady that I bought it from along with a note:

“I got your bike back to the divide.”

She responded appreciatively, and we exchanged a few well-wishes before I got back on my bike.

It’s very literally all downhill from here.

From the divide on, the trip down to Cumberland is super fast. It’s the steepest point of the downhill towards DC, so we absolutely flew on through for twenty miles, taking a few moments to appreciate the Big Savage Tunnel and the Mason/Dixon line. Tim had never made this trip before, a fact I was surprised to learn while we were riding RAGBRAI last year. He said that he had always wanted to but never had the opportunity, and that’s what led to us making this trip in the first place. Because of this, we ended up running into a ton of landmarks along the way that Tim had never seen before, and it was worth stopping for most of them so he could see them for the first time.

The one thing that went very wrong on this trip happened on the third day, which we started at the end of the C&O in Cumberland and rode towards Hancock, MD. I made a bad call on routing that day, leading us to accidentally skip the last town before a particularly empty stretch with very few possible stops. For anybody reading this, stop in Paw Paw, West Virginia and load up on water / snacks / supplies at the stores in town. You will appreciate it later. There is almost nowhere to stop for the next 40 miles or so, there is very little drinkable water along the trail, and the little drinkable water you will run into will be iodine treated and come from a janky, muscle-powered pump (“muscle-powered” meaning your muscles, specifically) that may or may not seize up while you’re using it. I didn’t realize that we missed the opportunity to stop in Paw Paw until we were a few miles up the road, and turning back would require us to go back through the Paw Paw tunnel: a dark, bumpy and narrow passage that feels more like a spooky cave than bike infrastructure. As a group, we decided to press on instead of going through the tunnel again, and an hour or so later we regretted this decision. It was 100 degrees out, we had no water, no water filters, and it was kind of rough. We reached a point where I was casing the few buildings we came across for external spigots I could steal water from, and still came up short. Tim and I may have rolled the dice a bit and drank some untreated water. Neither of us ended up with giardia as far as I can tell, but it was still a bit dicey.

It was a hundred degrees out so we immediately went walking to find beers as soon as we got to Hancock

The plus side of being dehydrated on a hundred degree day was realized when we got to Hancock. There’s a bike shop right along the trail at the edge of Hancock, and that bike shop sells cold drinks. I bought a can of Pepsi and two gatorades. I swear to all things holy, that Pepsi was the best thing I have ever drank in my entire life.

Seriously, if you’ve never had a cold can of Pepsi after biking 40 hot miles without water, you’ll never understand what the word “satisfaction” means.

Once we got settled into our accommodations for the night, the three of us went to dinner at BuddyLou’s, a local restaurant / gift shop / antique showcase that is really worth stopping at for food, beers, and unique decor. One thing that I think is worth mentioning about our overnight stays is that we mostly stayed in AirBnBs. I’m not usually one for AirBnB for trips to cities and places in civilization, but for little towns along a long bike trail, it’s really nice to get to a place with multiple bedrooms and working kitchens. More importantly, it’s really nice to have laundry facilities available along the way. Three of the four places that we stayed had in-unit laundry machines, and that meant that we never went more than two days without the option to do laundry. Because of this, it was easy to pack light as far as clothing is concerned, even if I probably still packed more clothes than I could have possibly needed. At least I wasn’t hauling wet, gross laundry around for any more than a day at a time, though.

It’s hard to describe how dusty your bike, you, and everything you have will get during this trip.

Jackie got a flat in Hancock, the only real setback we saw once we got out of the city.

Our fourth day had us going between Hancock MD and Harper’s Ferry WV. This was probably the least eventful day altogether, though the C&O is really pretty along this stretch of the route. At some point I got screamed at by a large group of what Jackie suspects were Cornish chickens. I saw at least a thousand turtles sunning on logs in the water running along the trail. There were multiple herons who seemed to just be showing off their wingspans for us. I don’t really consider myself an outdoorsy person, as while I do spend a ton of time on a bike or running outdoors, this time is almost spent entirely within city limits. Despite this, biking along a canal surrounded by wildlife never fails to make me feel like the world’s ultimate outdoorsman. (Outdoorsperson? I don’t know what the right word is, but it makes me feel exceptionally outdoorsy. )

We also stopped at Fort Frederick State Park which is right along the trail outside of Big Pool, MD. They’ve got a huge, reconstructed stone fort shaped much like the outline of Fort Duquesne that you can still see on the ground in Pittsburgh’s Point State Park. It’s honestly pretty neat to see a fully built structure in that shape if you’ve ever been in Point State Park and noticed the outline on the ground. They also have water and bathrooms there in the park, which made it a very welcome stop for our party.

Our arrival into DC on the last day went flawlessly. I spent a lot of the day just absolutely vibing to a biking playlist piped through my headphones while bombing through the woods. It was 100 degrees out, but the shade from the trees made for perfect conditions, and if you’ve never just pedaled the shit through some woods while listening to Steppenwolf’s Magic Carpet Ride at full volume, you are missing out.

This trip was largely supported by Sheetz. Sadly, many of them did not sell beers.

We stopped along the way to take in the sights at Great Falls MD along the trail (“Great Falls” is not just a name, there are some pretty great falls to appreciate here,) and had a pretty decent lunch – with beers, obviously, for nutritional reasons – at a trailside cafe in White’s Ferry. No sooner than we crossed the line into the District of Columbia, a very enthusiastic couple who smelled like they had just gotten off of a long shift working at a marijuana factory stopped their car in a Georgetown parking lot to yell out the window asking me all about our trip and to congratulate us for the effort. It was the warmest welcome I could have asked for. I rode over to their car and spent a few minutes swapping bike stories through their window. They told us they were working up the distance to be able to make this same trip themselves. I hope they make it someday, and more so I hope they run into a couple stoners when they reach the end of their trip to offer them excessively warm and excited congratulations similar to those they gave us.

It’s not really a bike adventure until you start climbing up on top of tall shit and peering over ledges with no railings

One of several photos I messed up at the finish line.

From there, we went to Mile 0 of the C&O canal towpath, which is confusingly hidden despite the number of signs pointing towards it. I fumbled a few pictures, none of which came out well, and we went off to our hotels for the night. No more than ten minutes after I made it through the door of my hotel, it started absolutely pouring outside. A deep, torrential rain that would have been hell to bike through. Somehow, I had been biking for five straight days and only missed the rain by five minutes. I’ll take it.

If you ever make this trip, give yourself time to bike around DC after you get here. I lived in this area for years and still do a lot of work down there. It’s a very bikeable city with a lot of great things to see. On this trip, after we got into town and got a good night’s rest, we loaded up our bikes the next morning and headed to Busboys and Poets for brunch. It’s one of my favorite places to take people who have never been, as they have food for everybody, it’s a really cool spot, and they’ve got a killer bookstore in all of their locations around the District. From there, we went to the National Mall to get photos of our bikes leaning in front of all of the various monuments. Jackie bought us some unexpectedly expensive slushies from a truck along the mall which were delicious but also $12 each.

I took more pictures of flowers along this trip than anybody would consider reasonable

From there we spent a couple hours biking to and walking around the United States Botanic Garden in DC as Jackie is a plant nerd and I’m an avid gardener. It’s really worth a trip, especially if you appreciate Phipps Conservatory. We had a couple hours to kill after that, so we did an abbreviated tour of the National Museum of American History before biking over to Reagan National Airport, where we rented a one-way pickup truck to haul our bikes back to Pittsburgh.

With that, our adventure was over. This entire trip brought an odd mix of emotions and introspection I wasn’t really expecting. The entire trip was just a weird reminder of how old I’ve gotten and how much I’ve grown as a cyclist. When I first attempted this in 2013, I was on a shiny, brand new bicycle and worried about every single detail of the trip. I was 32 years old and didn’t have any idea what I was doing. This time I was on effectively the same bike, now old and scuffed, a patchwork of repairs and replaced parts with thousands of miles of it. I’m also considerably older now, with experience I’ve earned biking in all sorts of conditions over the years. I always used to wonder when I’d become one of those old guys you see biking around without a care in the world, not giving a shit about the minor issues, and I think I missed when it happened.

I probably still don’t have any idea what I’m doing right now, but that’s for future me to decide.