Travel Day to Cumberland (Amtrak)

Last year, about this time, Fred and I set out to ride from Pittsburgh to DC, ready for the adventure ahead. Unfortunately, Fred ran into a mechanical issue that kept him from finishing the ride. I promised him I would fly back to DC and complete the journey with him, and ended up finishing the ride solo—except for the last day, when a couple of old friends joined me. Paula, Fred’s wife, gave us a ride to the Amtrak station, and Fred and I rode to Cumberland. After checking into the hotel, we found dinner where our other three riders met us. Together, we set a start time for the next morning, ready to tackle the road ahead.

Day 1 - Cumberland to Hancock 64 miles

We met our other three riders at mile marker zero in Cumberland under a pale, chilly morning sky, teeth-numbing but buzzing with excitement; after quick hellos and gear checks we rolled out together, laughed through one unexpected detour that sent us weaving along a quieter backroad and added a scenic surprise, then refueled both bikes and ourselves with a memorably humble lunch inside the Paw Paw, WV gas station—sandwiches on paper plates, picnic tables, backwoods West Virginia charm and the kind of roadside camaraderie that makes the ride worth it.

We arrived in Hancock, Fred and I stayed at a very quaint B&B. I stayed here last year and the service, and setting was perfect. Dinner was across the road, so not far to walk. Fred and I walked over a little early to begin the refueling process (it always starts with a couple beers). The rest of the riders (who stayed at a hotel down the street) finally joined us. Dinner was great and we all went back to our respective lodging. Fred and I sat on the porch enjoying a glass of wine. If

Day 2 - Hancock to Sheperdstown (65 miles)

After another early start, we found the trail and headed toward Shepardstown. The first 10 miles was easy rolling as this one section was a paved Rails-to-Trails section. scenery was filled with more farmland and more trailheads, each an opportunity to meet other riders as well as to enjoy a short break from pedaling. Fred and I picked a different hotel again as the other 3 wanted to ride longer and make it a 3 day ride while we were going to make our day 3 a short day and finish on the 4th.

We found a great German style brewery and restaurant; both were delicious. We even got a ride from one of the staff back to our hotel. Giving them our hard luck story that we could find an Uber, they gave us a ride. Back to that West Virginia charm.

Day 3- Sheperdstown to Brunswick MD (24 miles)

Only 24 miles made it a short day, but the last couple miles through town and up to the hotel felt like a mountain climb — steep, lungs-burning, and worth every pedal. We rewarded ourselves with a stop at another local brewery for a long, cooling lunch, then settled in with Chinese takeout for dinner. The short day was a welcomed break: easy miles earlier gave us time to linger, taste the town, and recharge for whatever tomorrow would throw our way.

Day 4- Brunswick MD to MM Zero Georgetown (60 miles)

Last morning, same SOP: hotel breakfast, load up, and hit the road — the simple rhythm that makes departures feel like part of the ride. It was our last day on the trail, again with great weather that reminded me how different this year felt compared to last year when five of six days were rain-soaked. This year clear skies, warm sun, and the camaraderie of fellow riders turned every mile into a memory worth keeping. I savored the smooth stretch of road, the laughter at rest stops, and the shared stories that made this trip more than a route on a map. Already looking forward to next year’s adventure.