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Biking and Hiking

Shepherdstown and the surrounding area presents a mix of opportunities for visitors with a variety of outdoor interests. There is certainly no shortage of places to hit the mountains and trails, with several state parks close by, and a landscape of mountains and woodlands in every direction. "*" == dog-friendly, leashed

Download the AllTrails app as the ratings, directions and feedback from other hikers may be helpful.

Shepherdstown Pedal & Paddle

Bike, kayak and canoes shop offering sales, service and rentals. They also organize group bike rides.

115 W. German Street
Shepherdstown, WV

EVENT: CASA River Century

A self-paced cycling event with 25, 50 & 100-mile routes.

Shepherdstown, WV

EVENT: Potomac Pedalers Back Roads Century

Rides for all levels with distances from 23 to 101 miles.

Shepherdstown, WV

The C&O Canal *

The C&O Canal trail runs nearly 185 miles, from Washington, D.C., to Pittsburgh, PA, and Shepherdstown sits perfectly along the route for bikers, campers, and nature lovers in general.

Lock 38, Shepherdstown, WV

Antietam National Battlefield *

Snavely Ford Trail

Here’s a pleasant circuit walk along the surprisingly wild Antietam Creek less than a mile from the C&O Canal. The hike meanders along one of three fronts in the Battle of Antietam.

Three Farms Trail

Easy to moderate with a nice mix of water, woods and fields​​.
Sharpsburg, MD

Potomac Valley Audubon Society Preserves

Yankauer Nature Preserve *

The preserve encompasses a total of 104 acres. Most of the land is gently rolling former farmland that is gradually returning to its natural forested state. The preserve also includes a section of wooded, high limestone bluffs overlooking the Potomac River.

Whiting’s Neck, WV

Cool Springs Preserve *

The preserve consists of 63 acres of forest, meadow and marsh in southern Jefferson County, West Virginia. Bullskin Run, a major stream with significant historical value, borders one side of the preserve. Cool Spring is designated as a “birding hotspot.” In Spring 2020, the entire preserve was placed under a conservation easement with the West Virginia Land Trust.

SW of Charles Town, WV 

Eidolon Preserve *

The 354-acre Eidolon Nature Preserve is located along the summit and east side of Sideling Hill, in Morgan County, West Virginia. The preserve features dense mountaintop forests, several ground-fed natural springs and commanding views of the Potomac River.

Great Cacapon, WV

Stauffer's Marsh Preserve *

Stauffer’s Marsh Nature Preserve consists of 46-acres of primarily wetland in Back Creek Valley in Berkeley County, WV. Formerly marshy farmland, the USDA restored the wetland ponds and marshes as a part of the Wetland Reserve Program. Today, Stauffer’s Marsh is a paradise for migrating and nesting waterfowl.

Hedgesville, WV

Ferry Hill

Across the bridge from Shepherdstown, opposite where you get on the C&O. It can be a tough hike when its muddy out. But you always have the option of dropping down to the tow path.

Shepherdstown, WV

Murphy Farm

Go towards the Harpers Ferry KOA and you will see signs. Nice wooded trail and an overlook to the Shenandoah River.

Harpers Ferry, WV

Bolivar Heights

This trail (0.4 to 2.4 miles) is easy to moderate and can take anywhere from 15 mins to 1 hour to complete. Bolivar Heights offers some of the best views of the Blue Ridge Mountains, Potomac River water gap, and the Shenandoah Valley with the least amount of walking.

This trail begins at the Bolivar Heights parking area (end of Whitman Avenue, Bolivar, WV 25425) with a 0.3-mile loop on top of Bolivar Heights. This is the best place to survey the terrain, cannons, and earthworks reflect the violent history of this site. The 1.3-mile upper loop continues on the crest and then turns right, down a wooded trail to a lovely view of Schoolhouse Ridge. Here you can continue through the field 1.1 miles on the Lower Loop towards Lower Bolivar Heights or turn right and follow the tree line to another wooded trail back up to the Bolivar Heights parking area.

Visit this NPS page for more information.

Bolivar Heights, WV

School House Ridge (South)

School House Ridge North is not great as there are park service vehicles in and out all the time, so you do need to be on leash. South is across 340 on Millville Road, slightly wooded/open field with trails. Super easy, also low traffic.

Harpers Ferry, WV

Blue Ridge Center for Environmental Stewardship *

10 miles of hiking to explore streams, spot wildlife, and imagine life in a 19th century farming community. Free to the public every day from dawn till dusk.

Purcellville, VA

Washington Monument State Park *

This state park is named for the first completed monument dedicated to the memory of George Washington. Most of the Washington Monument’s hiking trail is part of the Appalachian National Scenic Trail.

Atop South Mountain
Boonsboro, MD

Appalachian Trail *

The Appalachian Trail (AT) runs right through the quad-state area. There’s 42 miles of trail between VA, WV, MD and PA. It’s also super accessible, so point to point hiking can be achievable easily. On this particular section it varies from east to moderate with general incline and some roots and rocks. Further south around Front Royal and Round hill is a section of the AT called the “roller coaster” it’s about 3k vertical over about 12 ridges/gaps roughy 12ish miles point to point.

AT Headquarters - Harpers Ferry, WV

Also in Harpers Ferry is the Appalachian Trail Conservancy.

Jefferson Rock *

Several large masses of Harpers shale, piled one upon the other, comprise Jefferson Rock. The name of this landmark derives from Thomas Jefferson, who stood here in 1783.

Harpers Ferry, WV

Maryland Heights Trail *

Maryland Heights is another of those must-do circuits for most hikers in the metro area. With a spectacular view of Harpers Ferry from the main overlook, and steeped in Civil War history, this shorter circuit is a favorite for many.

Harpers Ferry, WV

Weverton Cliffs *

Weverton Cliffs is a 1.9 mile heavily trafficked out and back trail that offers the chance to see wildlife and is rated as moderate. The trail is primarily used for hiking and running; accessible year-round.

Knoxville, MD

Cacapon State Park

You can’t get bored at Cacapon when there’s 23 miles for hiking on 9 different trails waiting to be explored. No need to worry about getting lost, as hiking guides are available at the park office. Each trail offers a different physical challenge depending on skill levels, so there’s something for everyone.

818 Cacapon Lodge Dr., Berkeley Springs, WV 25411

Cunningham Falls State Park and Gathland State Park *

Frederick, MD

Other trails (not necessarily nearby!)

To the west lies the Allegheny trail (circuit alternate to the AT), Otter Creek, Cranberry Glades, Dolly Sods and Seneca. All are great! There’s also Monongahela National Forest in central east WV, has miles and miles of trails with low traffic. Also some of the last virgin old growth forest on the east coast and even an area classified as alpine tundra! Michaux State Forest (PA) has some nice hiking in it. A bit to the western side of the state of PA is the Tuscarora Trail which is another long distance trail made up of many smaller circuits.

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