The Press Room
The Press Room is a restaurant that could have been plucked out of D.C. and placed into Shepherdstown. The dishes are innovative, fresh, and most importantly, delicious. Bikers may want to shower before stopping in.

Pressed Flour
This tiny bakery is a local legend. Although it is only open Thursday through Sunday, the entire town waits all week to line up for these baked goods, served from a small window on German Street.

Maria’s Taqueria
A Shepherdstown local was quick to tell me that, “Maria’s is Tex-Mex, there is no doubt about that. However, that doesn’t mean it ain’t good.” After hundreds of miles on the trail, tacos, nachos and warm plantain chips sound really good.

Harpers Ferry, WV – Mile 273.8

Harpers Ferry, WV, is a name you may recognize from history class. This well-preserved town is famous for its role throughout the Civil War, including the raid of John Brown. In October of 1859, Brown led a group of abolitionists on an assault of Harpers Ferry Arsenal hoping to collect weapons to start a slave uprising. The raid failed and Brown was hung for his crime, but the aftermath increased tension between the north and south.

Riders who stop in Harpers Ferry get the chance to envision the town during this era, as the historic downtown appears as it did hundreds of years ago, with cobblestone streets, brick buildings and even a wax museum dedicated to the story of John Brown. It’s a beautiful spot.

Where to stay:

Teahorse Hostel
The Teahorse Hostel is a bargain. The space is clean and has free wifi and breakfast. The hostel is popular with Appalachian Trail hikers, and it’s fun to swap travel stories in the common room with the other guests.

Don’t miss:

Appalachian Trail
For those who have extra time, the Appalachian Trail cuts directly through Harpers Ferry. C&O trail riders have a chance to take a break from biking and hike part of this famed path. Additionally, the scenic Skyline Drive is just a one-hour drive from Harpers Ferry.   

Photo by Madeline Quigley.

Leesburg, VA via White’s Ferry over the Potomac River – Mile 299

Only 35 miles outside of D.C., riders have the unique opportunity to cross the Potomac River on White’s Ferry. Many of the towns on the GAP and C&O trails were historically dependent on their ferries, so it brings the trip full circle to cross the river this way.  

Things to see:

Ale Trail
Loudoun County is home to 21 craft breweries, five of which are in Leesburg. The county has devised an “Ale Trail” that shows visitors breweries in the area and shares information on the type of beers they produce.

Wineries
In addition to beer, Loudoun considers itself part of “D.C.’s Wine Country.” The area has 42 vineyards.  

Washington, D.C. – Mile 334.5

Expect to cruise into Georgetown dirty, tired and craving a hot meal.

Where to eat:

Chaia 
Many riders head to the riverfront to enjoy a breeze (and a beer) after completing the ride, but a D.C. favorite, Chaia, is only a few blocks from the terminus of the trail.  Chaia features farm-to-table, innovative and seasonal vegetable tacos.  Toppings like poblano crema, chipotle yogurt, queso fresco and smoked salsa make these tacos a flavorful first meal off the trail.

Getting back to Pittsburgh: Assuming you’re not up to bike back, riders have a few choices when it comes to getting home. Some people have a friend pick them up, some fly, and some take the train. Amtrak has a line from D.C. to Pittsburgh and there are special seats for bikes. Only six of these are available per train, so be sure to book in advance.

Photo by Madeline Quigley.

If you have ridden the GAP or the C&O, share your favorite spots in the comments below!

Madeline Quigley

Madeline Quigley is a food/travel writer in Pittsburgh.