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.