Distance: 44 miles | Terrain: Easier | Town Hill Bed & Breakfast
The trip begins with an 8:30am Meet’n’Greet in D.C. Bring your luggage and be ride-ready. After brief introductions, we will load the van and trailer. We will shuttle to Cumberland to start our ride on the C&O. We pedal through constantly changing scenery of secluded forests, suburban developments, and everything in-between. The highlight of today’s ride is the 3,118 foot-long Paw Paw Tunnel, one of the world’s longest canal tunnels. Other sites on today’s ride include the Town Creek Aqueduct and a fully restored section of the canal at the historic Oldtown. At the end of the day, we’ll convene for dinner at Bill’s Place, a combination general store and pub with a lot of character. Be sure to check out the ceiling of dollar bills. We’ll have a group dinner tonight.

Distance: 45 miles | Terrain: Easier | Red Roof Inn
Today you’ll pass through Hancock, which, at one time, was a major inland port. A little later on, you’ll pedal past the Licking Creek Aqueduct, the largest of six single-arch aqueducts along the trail. You’ll visit the 18th century Fort Frederick, which was used for various purposes during the French & Indian and Civil Wars. You’ll also see the ruins of the Tonoloway Creek Aqueduct and the Round Top Cement Company. We’ll spend the night in Williamsport, a city that played a large role in transportation during the heydey of the canals. We’ll have dinner tonight at 6:30pm

Distance: 29 or 35 miles | Terrain: Easier | Bavarian Inn
You’ll begin today passing the Conosocheaque, an aqueduct that is missing its upstream wall, thanks to recent collapses. You’ll ride past the Killiansburg Cave; look 50 feet up in the foliage to see the cave that provided shelter for townsfolk during the Civil War. Just outside of Sharpsburg, extend your ride by a few miles to visit the Antietam National Battlefield, the site of the Civil War’s bloodiest battle. History buffs may want to spend a few hours exploring the battlefield. We’ll spend the night in Shepherdstown at the charming Bavarian Inn. Tonight’s dinner will be at 6:30pm at the Bavarian Inn.

Distance: 43 miles | Terrain: Easier | Leesburg Colonial Inn
The highlight of today’s ride is Harper’s Ferry, a National Historic Site famous for wars and floods. Located at the fork of the Potomac and Shenandoah Rivers, you’ll take the footbridge across the river to visit the charming town. For the three miles after Harper’s Ferry, keep your eyes open for thru-hikers traveling the 2,000 mile-long Appalachian Trail (known as the “AT”), as the AT joins the Towpath through this section. While passing through Point-of-Rocks, check out the railroad station -- one of the most photographed in Maryland. Pass the impressive Monocacy Aqueduct, a 500-foot, seven-arch stone bridge. Near the end of the day, take the Whites Ferry, the last operating ferry on the Potomac, to cross the river and get to our inn at Shepherdstown.

Distance: 40 miles | Terrain: Easier | Le Meridien Arlington
Today’s ride is along one of the busiest sections of the C&O Canal Towpath. You’ll see the Seneca Creek Aqueduct, the last along the towpath. Pass beautiful Swain’s Lock and then stop for lunch at the scenic Great Falls, popular with hikers, kayakers, and rock climbers. In the final miles into Washington DC, the path will become much more urban. You’ll pass the half-mile long David Taylor Model Basin, a building where the Navy tests model scales of new ships. You’ll also pass the area known as “Seven Locks,” with seven lift-locks along a short 1.25 miles of the canal. We’ll end the day in Alexandria, Virginia, just across the Potomac from Washington DC - Georgetown. We’ll share our final dinner together tonight at Clyde’s of Georgetown.

Distance: 13 miles | Terrain: Easier | Includes Bike Tour of Washington D.C.
Today we will take a professionally guided bike tour of Washington DC, visiting many of the iconic sites of our nation’s capital. As we follow an interconnected series of bike paths weaving through the downtown area, your guide will entertain you with poignant, fascinating, and incredible stories about Presidents, Congress, memorials, parks, spies, and scandals. After our DC tour we’ll say our goodbyes.