Day 1 on the C&O Canal

 I’m writing this from a front porch glider at Bill’s Place in Little Orleans, the kind of spot that feels like it hasn’t changed in decades—and thankfully so. It’s the perfect place to exhale after our first day on the Chesapeake and Ohio Canal, legs pleasantly tired and a cheeseburger-and-fries kind of satisfied.

The morning started with a bite in the air, the kind that has you second-guessing your layering strategy. But as the miles ticked by, the sun did its job and one by one, the extra layers disappeared into jersey pockets. What we were left with was just about perfect riding weather and a ribbon of trail that delivered all day long.

The highlight—no question—was rolling through the Paw Paw Tunnel. At nearly three-fifths of a mile, it’s long enough to feel like you’ve entered another world. The darkness swallows you up, the temperature drops, and the sound of your tires echoes off the damp brick walls. Then, just as you settle into the rhythm of it, you see the light ahead—and bursting out the other side feels nothing short of spectacular.

We also had plenty to look at beyond the trail itself. Wildlife was out in force—mostly painted turtles sunning themselves on logs in the canal, completely unconcerned with our passing. We spotted a couple of wild turkeys, plenty of Canada gooses, and ducks along the way. Add in trees just starting to pop with spring blooms, and the whole ride had that fresh, early-season feel that’s hard to beat.

The riding itself? About as good as it gets. Long stretches of smooth, “champagne” gravel made for effortless cruising, the kind of surface that lets you forget about the bike and just enjoy the ride. No real suffering to speak of today—just a steady, rewarding 44 miles in the books.

Rolling into Bill’s Place was the ideal finish. Simple, classic, and exactly what you want after a day like this. Cheeseburgers, fries, and that deep, earned contentment that only comes from hours in the saddle.

What made the day even better, though, was the nostalgia. This stretch of the canal isn’t new to me. As a kid growing up around here, I spent plenty of time along the C&O—canoe trips, Boy Scout outings, family hikes. Riding it now feels like flipping through an old photo album, except this time I’m doing it on two wheels.

Tonight’s lodging is at the Town Hill Bed and Breakfast, and JP and I took care of the shuttle logistics like responsible adults. Johnny Mac, on the other hand, has different plans. Apparently, 44 miles of smooth gravel wasn’t quite enough. He’s opted to tack on an extra nine miles—straight up—with about 1,600 feet of elevation gain.

Every group ride has one. Johnny Mac just volunteered.

Met some other bikers at our Bed and Breakfast that had a car, and we got a ride to Berkeley Springs WV.  Proof restaurant was very nice. 

Day 2 on the C&O Canal

Day two began high above it all—perched at 1,680 feet on Town Hill, looking out over western Maryland from our cozy Airbnb. The morning started right, thanks to Lisa, our bed-and-breakfast host, who put together a truly glorious breakfast that set the tone for the day.

From there, we caught a shuttle down to Bill’s Place, dropping us toward the Potomac River and the I-68 gap. The descent was dotted with redbud trees in full bloom—bursts of spring color that made it hard to focus on the road. We even crossed paths with Mac on the way down before arriving at Bill’s Place to pick up the Western Maryland Rail Trail.

The rail trail itself was a dream—freshly paved, smooth, and fast. We cruised along for 27 miles, soaking in one of those perfect spring days where everything just clicks. Around mile 17, we paused in Hancock, making the obligatory stop at the post office and the C&O Bike Shop. It was here that Mac made a bold—and necessary—decision: the iPad had to go. One quick mailing later, and just like that, the weekend was officially work-free.

As the miles rolled on, so did the people. More cyclists appeared—many on e-bikes—and hikers too, especially as we approached Williamsport. About five miles north of town, we passed a U.S. Park Ranger who seemed to be dealing with some vaguely described “nefarious hillbilly goings-on.” We chose not to investigate further and kept the pedals turning.

Our riding strategy for the day evolved into something a bit more… seasoned: ride 10 miles, stop; repeat until mile 30, then shift to stops every five miles for a quick stretch. Call it age-appropriate optimization for the 60+ crowd.

Williamsport greeted us with history. Our first stop was the Chesapeake and Ohio Canal National Historical Park museum, where we got a fascinating look into the canal’s working life—right up until its closure in 1924. It added a deeper appreciation for the path we were riding.

The day wrapped up just outside town at Shady Sycamore Farm, a charming Airbnb run by our host, Keely—one of the “super hosts” who truly lives up to the title. Later, we headed into town for dinner at Ric’s Restaurant, where we met Ric himself. Small-world moment: he knew Lenny from the Stained Glass Pub. Connections like that seem to find you out here.

Back at the farm, we caught the splashdown of the Artemis program off San Diego—an incredible sight and a fitting capstone to the day. There was a shared sense of accomplishment in the air, the kind that comes after a long ride, good food, and meaningful moments.

Another glorious day along the C&O Canal—about 42 miles in the books. This place really is a national treasure.

Day 3 on the C&O Canal

Day 3 — Unexpected Company and a Gritty Finish

Well, day three is officially in the books—and it came with a twist none of us saw coming.

We woke up at the Shady Sycamore Airbnb at Keeley’s place in Williamsport, Maryland, to a surprise arrival: Tom Mercer, standing there like he’d been part of the plan all along. None of us had any idea he was coming, which made for a great (and slightly surreal) start to the morning.

We rolled first into the Williamsport Diner, a classic old-time spot that felt like stepping back a few decades—exactly the kind of place you hope to find on a trip like this. Fueled up, we set out on what we thought would be a straightforward 45-mile day from Williamsport to Brunswick.

Of course, the trail had other ideas.

Not long into the ride, Tom started feeling the effects of what looked a lot like food poisoning. As we made our way toward Harpers Ferry, it became clear this wasn’t something he could just push through. The pace slowed, and the focus shifted from miles to making sure he was okay.

Near Harpers Ferry, we were able to connect him with EMT support, which got him a few miles further down the line. Then, in a pattern that’s becoming a theme of this trip, another act of kindness stepped in—our third Good Samaritan couple in as many days—who drove him the rest of the way to Brunswick and safely to our Airbnb.

With Tom taken care of, we pressed on and finished the ride strong, logging about 47 miles by the time we rolled into town.

Our home for the night is an old brick house on the corner of Potomac Street, directly across from City Hall and just steps from the C&O Canal towpath—about as perfect a location as you could ask for on this ride.

Dinner brought us to Smoketown Brewing, where Mac and I opted for nonalcoholic beers to cap the day. We closed things out back at the house with a few episodes of Breaking Bad, a fitting wind-down after a day that had a little bit of everything.

All told, a good day on the trail. The trees are starting to show fuller buds, greener by the mile as we head south. We’ve now crossed the 130-mile mark, and you can feel the journey settling in—on the legs, on the gear, and in the rhythm of the days.

Traffic on the towpath is picking up too—more cyclists, more pedestrians—and we’re expecting tomorrow to be our busiest yet.

And then there’s the dust. It’s everywhere now, coating the bikes and gear in a fine layer that somehow feels like a badge of honor at this point.

Tomorrow is the big one: 55 miles.

Let’s see what the trail has in store.

Day 4 on the C&O Canal

Day 4 – C&O Canal: A Perfect Finish

Day four on the C&O Canal ended every bit as gloriously as it began. We had 55 miles ahead of us, and the ride delivered something special with every passing mile.

What stood out most was the transformation of the landscape. Back in Cumberland, the trees were still mostly bare—just hints of spring beginning to show. But as we made our way toward Washington, DC, the scenery evolved steadily. Buds turned into blooms, and before long, we were riding beneath a full, leafy canopy. It felt like pedaling straight into spring.

The miles rolled by easily as points of interest appeared along the trail, each adding a little character to the journey. There’s something about the C&O that keeps you engaged the entire way—history, nature, and the simple rhythm of the ride all blending together.

As we approached Georgetown, we half expected heavy crowds, especially with it being a beautiful Sunday. But to our surprise, it was pleasantly manageable. The canal towpath remained enjoyable, and Georgetown itself had just the right amount of energy—lively, but not overwhelming.

We did run into one small hiccup at the end: the elusive Mile 0 marker. Unfortunately, it sits tucked away inside Thompson’s Boathouse, and we weren’t able to track it down. A slightly imperfect ending—but honestly, it didn’t take away from the accomplishment.

Fifty-five miles, a changing landscape, perfect weather, and a smooth roll into Georgetown—it was a fitting end to a truly memorable ride down the C&O Canal.