Starting in Connellsville and heading to Cumberland, you’ll cover 88.8 miles over two days on what was once the Western Maryland Railway’s extension into Pennsylvania.
Your first 27 miles or so will be through the thick forest canopies of Ohiopyle State Park, while crossing high above the bubbling Youghiogheny River twice. Take an easy hike around Ferncliff Peninsula, a reknowned spot for rare wildflowers. Have lunch at a cafe in Confluence, and cross the Casselman River twice on your way out of town. Two more river crossings on either side of the Pinkerton Tunnel, and you finish in Rockwood, where there are lodging properties very close to the trail.
Your second day features a fifth Casselman River crossing using the soaring Salisbury Viaduct, a visit to Meyersdale for lunch, and then eight crossings of Flaughtery Run as you head to the Mason & Dixon Line. In Maryland, you’ll catch wooded valley vistas on the 20.5 remaining miles downhill to Cumberland, where dinner, a glass of wine, and an evening ride on Amtrak’s Capitol Limited back to Connellsville awaits.