DAY 1. CUMBERLAND TO LITTLE ORLEANS (43 MI.)
Riding out of Canal Place in Cumberland, you begin your trip on the C&O Canal Towpath. The towpath was a historic engineering marvel, and you’ll see why as you ride its 185 length. The Paw Paw Tunnel is a particular highlight of your ride today (be sure to have a light) and perfect for photos ops. Upon reaching the Fifteenmile Creek Recreation Area you’ll take the turn up the road to Bill’s Place and stop for dinner. Call your B&B to arrange for your shuttle ride up the hill and learn why Town Hill B&B is a piece of National Road history and unbeatable kitschy fun!
Meals: On Own
Overnight: Little Orleans
DAY 2. LITTLE ORLEANS TO WILLIAMSPORT (41 MI.)
After a shuttle back down the hill to the towpath, you can choose to ride the C&O all day or take a break on the paved Maryland Scenic Rail Trail which parallels the towpath just west of Hancock and then beyond to Fort Frederick. Stop in the town of Hancock for lunch. For history enthusiasts a stop at the reconstructed 18th century Fort Frederick may be in the cards. End your day in the canal town of Williamsport.
Meals: Breakfast
Overnight: Williamsport
DAY 3. WILLIAMSPORT TO SHEPHERDSTOWN (27.5 MI.)
After breakfast in Williamsport it’s back onto the C&O and more riding. The Big Slackwater section (around MM 85) is unique on the towpath as you ride on a cantilevered concrete path above the Potomac River. You can ride on water! Entering the heart of Civil War history, end the day in Shepherdstown, Wv., just across the Potomac from Sharpsburg, Va. and Antietam National Battlefield. Civil War buffs will want to take a half-day to visit the battlefield – biking is allowed in the park.
Meals: Breakfast
Overnight: Shepherdstown
DAY 4. SHEPHERDSTOWN TO BRUNSWICK (18 MI.)
*Due to the closure of the Whites Ferry, access to lodging in Leesburg, Va., is not practical. This allows for a shortened day to visit sites along the trail including Antietam National Battlefield and Harpers Ferry, followed by a final push into DC.
Shepherdstown may be one of the cutest college small-towns in the US and has some tasty cafes and bakeries, plus great boutiques and book stores. You may find it hard to leave! The C&O Towpath today continues into Civil War country and you’ll pass by multiple historic markers and structures – including several reconstructed aqueducts which were built for the canal. At MM 60.8 you’ll want to take a trail break and walk over to Harpers Ferry, Wv. The Lower Town is part National Park Service exhibit, part art shops and boutiques, and all charm. It’s also a perfect place to find lunch.
Meals: Breakfast
Overnight: Brunswick
DAY 5. BRUNSWICK TO DC (55 MI.)
After breakfast, begin your last day of riding on the C&O Canal Towpath. The trail here is well traveled and highlights include Great Falls Park (a good lunch stop), Georgetown, and Washington, D.C.! Your destination is Mile Marker 0 (we provide mapping and text since it can be a tricky marker to find) and the end of an incredible journey.
Meals: Breakfast
Spend the night in Washington, D.C. before meeting your return shuttle, if included.
Post-Trip Option: Spend an extra day or two in D.C. and explore the many bike trails that follow the Potomac, bike around the National Mall, visit some museums, or even take the Mount Vernon Trail all the way to Alexandria and George Washington’s Mt Vernon plantation. We’re happy to help provide suggestions, reservations, and planning.