Shepherdstown is an under-the-radar arts enclave and outdoor utopia in the lower Shenandoah Valley. Situated at the confluence of the Shenandoah and Potomac Rivers, the small town offers a unique mix of past and progressive. Historic buildings with weathered charm dating back to the 18th century sit beside hip coffee shops and eclectic restaurants, enjoyed by Shepherd University students and city transplants like David Lillard, who moved 90 minutes west from Washington, D.C., 15 years ago and never looked back. Lillard, editor of the West Virginia Observer and an author of guidebooks including Exploring the Appalachian Trail in Virginia, found Shepherdstown while biking with his wife on the C&O Canal Towpath, which runs by town on its 184-mile route between D.C. and Cumberland, Md.

“In some ways we got on our bikes and moved 70 miles upriver,” says Lillard.

In addition to the river access and close proximity to the C&O, Shepherdstown is a recreation hub for Appalachian Trail hikers and explorers of the nearby Harpers Ferry National Historical Park and Antietam National Battlefield. After a day at play, you’ll find friendly locals and adventurous visitors grabbing a beer at Stonewall’s Pub or watching an independent film at the Opera House.

“It’s an interesting blend of people who are into the arts and the outdoors,” Lillard adds. “This is a town where you’re always going to run into someone that you know, but I’ve been here for 15 years and I’m still regularly meeting people.”

Shepherdstown is the oldest town in West Virginia. Originally called Mechlenburg, it was founded when the state was still part of Virginia. Illustration by Scott DuBar

Lillard’s Outdoor Picks:

Running Through History
Antietam National Battlefield might be the most scenic, safest road run in the East, with views of the Blue Ridge in the distance and battle monuments all around. Choose from an easy rolling circuit or a brutal climb from the creek to the observation tower.

Hiking Above Harpers Ferry
Thomas Jefferson said the view from the rocks above Harpers Ferry was worth a trip across the Atlantic. For the best views, head across the Potomac in Maryland for a short but strenuous hike up Maryland Heights.

Skiing the Legacy Loop
Twelve miles from Shepherdstown in Loudoun, Va., is the 900-acre Blue Ridge Center for Environmental Stewardship. Nestled below the Appalachian Trail, its 10-mile trail system, especially the Legacy Loop, offers solitude and wildlife.

Bike Camping
Want a quick escape for a night under the stars? Peddle out of Shepherdstown and head upriver on the C&O Canal’s towpath. The first biker campsite is just a couple miles away. In the long days of summer, you can set up camp, ride into town for burgers and beers, then back out in time for dark.

Easy Paddling
One of Shepherdstown’s greatest assets is the Princess Street boat ramp. Within a few miles, there are two put-ins upstream and one downstream. Sure, you’re just outside town, but once you’re on the water, you’ll feel like you’re out in the wild.