Split the Journey Over Four Weekends

If you can’t arrange to take a week or so for the Ride of Your Life, you can still cover both the Great Allegheny Passage and C&O Canal Towpath (all 333.3 miles!) over four long weekends. Here’s one way to do it, with most days in the 25- to 35-mile range. Get picked up or rent one-way to return to your starting spot. This itinerary is largely amenable to lodging in nearby trail towns. It’s best for bicyclists, but hikers or ultramarathoners might find it doable with adequate training and perhaps a shuttle service to handle gear.

Weekend One: Downtown Pittsburgh to Confluence

This three-day jaunt carries you from Point State Park in Downtown Pittsburgh to beautiful Confluence in the heart of the Laurel Highlands. If you have time on day one, tool around Pittsburgh’s South Side before heading east toward Homestead, McKeesport, and West Newton. Day two takes you through Cedar Creek Park where there’s a lovely hike along Cedar Creek Gorge, and in Connellsville, travel the Connellsville Bike Loop around the town’s residential and commerical district. On day three, you’ll meander through Ohiopyle State Park with enough time to explore Ferncliff Peninsula or take lunch along the Youghiogheny River.

	Start	End	Mileage
Day 1	Downtown Pittsburgh	West Newton	34.7 Miles
Day 2	West Newton	Connellsville	25.3 Miles
Day 3	Connellsville	Confluence	27.2 Miles

Weekend Two: Confluence to the Paw Paw Tunnel

Over this long weekend, you’ll be traveling on both the GAP and the C&O Canal Towpath. Start in Confluence, and then stop in Rockwood for an early dinner and to enjoy a tour of town. Catch the sunset from the Salisbury Viaduct and conclude your day in Meyersdale. On day two, head east, where you’ll cross Flaughtery Creek eight times while approaching the Big Savage Tunnel. Check out the Borden Tunnel, built by the Western Maryland Railway to get its trains through the rugged Allegheny Mountains over 100 years ago. Spend a few hours in Frostburg for lunch and a tour of the college, or find an ice cream cone. Finish the day riding through Helmstetter’s Curve, peeking into the Cumberland Bone Cave, and arriving for dinner and overnight in Cumberland. The next day, depart for the Paw Paw Tunnel, and en route, explore some of the canal locks and aqueducts on the way. Arrange for a ride back after exploring a bit.

	Start	End	Mileage
Day 1	Confluence	Meyersdale	29.7 Miles
Day 2	Meyersdale	Cumberland	31.9 Miles
Day 3	Cumberland	Paw Paw Tunnel	28.4 Miles

Weekend Three: Paw Paw Tunnel to Shepherdstown

Start at the famous Paw Paw Tunnel, which once carried canal boats through the rugged Allegheny Mountains. Head east toward Hancock along a section of the C&O Canal Towpath known for its tightly-twisting course next to the Potomac River. Enjoy dinner and an overnight in Hancock. The next day, continue east, passing “Big Pool,” a wide section of the canal once suited for turning boats around, and Fort Frederick State Park, in which an 18th century stone fort remains standing and open for tours. Cross into Williamsport via the Railroad Lift Bridge, now permanently lifted and retrofitted for carrying bicyclists and hikers over the canal into town for dining and lodging. On day three, complete your eastbound ride to Shepherdstown, where you can explore the historic business district with its bookstores, cafes, art galleries, and restaurants.

	Start	End	Mileage
Day 1	Paw Paw Tunnel	Hancock	32.0 Miles
Day 2	Hancock	Williamsport	24.7 Miles
Day 3	Williamsport	Shepherdstown	26.6 Miles

Weekend Four: Shepherdstown to Washington, D.C.

Depart from Shepherdstown heading eastbound on the C&O Canal Towpath. Pause at Antietam Creek Aqueduct to recall that Antietam Creek “ran red with blood” after a fierce 1862 Civil War battle upstream resulted in over 23,000 casualties in just one day of fighting. Finish in nearby Harpers Ferry, where abolitionist John Brown once took over a federal armory. Spend day two hiking to vistas in Harpers Ferry National Historic Park, or walking its battlefields and taking in museums. That afternoon, make the short trip to Brunswick and check out the Brunswick Heritage Museum before settling in for the night. Wake up early for a longer day on the towpath, passing through spectacular Great Falls Park before ending your trip in Washington D.C.’s bustling Georgetown neighborhood.

	Start	End	Mileage
Day 1	Shepherdstown	Harpers Ferry	12.1 Miles
Day 2	Harpers Ferry	Brunswick	5.7 Miles
Day 3	Brunswick	Washington, D.C.	55.0 Miles