Williamsport

Williamsport sits at Canal Mile 99 — the literal halfway point of the C&O Canal corridor. Founded in 1787 by Revolutionary War general Otho Holland Williams and once seriously considered as a site for the nation’s capital, this small Maryland town has been a waypoint for travelers for more than two centuries. Canal-era boatmen stopped here to load and unload goods, and Civil War soldiers crossed the Potomac at this bend, most famously when Lee’s Army of Northern Virginia retreated through Williamsport after Gettysburg in 1863. Today it remains one of the most cyclist-friendly communities on the towpath.

The town’s main commercial corridor hugs North Conococheague Street, where a cluster of local restaurants, shops, and services face the Potomac River. The C&O Canal Grill & Pub anchors one end of the strip; the Sweet Notes Bakery and Ruth’s Market supply trail users with freshly made food for the next day’s ride. Cushwa Brewing Company, a short drive from the towpath, offers one of the region’s best craft brewery experiences in a converted industrial building.

For families, cyclists at the midpoint of a through-trip, and anyone who wants a dose of small-town Maryland alongside their canal adventure, Williamsport delivers.