Day 3 - Myersdale to Cumberland

137 miles down
183 miles to DC

After the demanding ride the day before, today offered a welcome change of pace—just 32 miles on the bike, giving everyone a chance to recover and soak in the scenery. It was a laid-back adventure, marked by scenic tunnels, sweeping overlooks, a crossing of the historic Mason-Dixon Line, and a blissful 22-mile descent after reaching the Eastern Continental Divide.

Kevin, our ever-energetic SAG support guru, keeps spirits high and hydration flowing. Not only does he haul all our luggage and set up snack stations at each stop, but he adds his own twist: once he arrives at the next rest point, he unloads his bike and pedals back up the trail to meet us, then rides with the group to the stop he just left. It’s a clever system that lets him log some serious miles—on our 50+ mile day, Kevin clocked in 25 miles himself! Kevin claims his shoes are for cross training - biking and driving.

Thom, our fearless senior ride leader, never misses a chance to tease Kevin. Yesterday’s highlight? Catching Kevin mid-chip munch and declaring that snacks were reserved for “real” riders. Their playful ribbing is more than just entertainment—it’s a reflection of the camaraderie and mutual respect that fuels their seamless teamwork in planning and leading this adventure.

The Great Allegheny Passage trail follows the path of a former rail line carved along the Youghiogheny River. Riverbanks, with their gentle grades, were ideal for laying tracks, and today they make for smooth cycling. Along the way, we pass remnants of old train stations and, across the river, still-active rail lines—a living reminder of the region’s industrial past.

One of the most enjoyable parts of the ride is arriving each evening in towns like Cumberland, Hancock, and—last night—Meyersdale. These communities, nestled in the heart of Western Pennsylvania and Maryland, carry the quiet charm of places that have weathered the decline of their industrial roots. Our stay last night was in a former tool factory, now transformed into a quirky, character-filled hotel. It's nothing if not eclectic, and each year we seem to have the entire place to ourselves.

We've settled into a quirky tradition: whenever we dine out, the waitress hands the check to Daniel—the smallest member of our crew. The other night, he confidently passed her a card to pay, only for her to pause, smile, and point out that he'd just handed over his Comfort Inn room key.

We finished off this evening with a game night, another way to bring the youngsters and adults in as a cohesive unit.Read more