Best Trails in Maryland

Trying to find the best trails in Maryland? Bivy has great hiking, biking, paddling, climbing, skiing, riding and more, with hand-curated trail maps, as well as detailed driving directions.


Virginia, Madison County

03 :08 hrs
6.3 mi
664.1326 ft

The Old Rag is a popular summit among the Shenandoah peaks because climbing it feels like an actual mountain, perhaps due to its rocky mount, unique among mountains in the Blue Ridge. This particular route begins from the parking area on VA 600 and follows the Ridge Trail up the spine of Old Rag. Continue following this trail along the rocky summit of Old Rag, soak in the views, and then descend along the easterly side of the mountain. When the trail rejoins Weakly Hollow Road, make a hard right along the Weakley Hollow Fire Road that parallels the main road. This will eventually return to the parking area.


Virginia, Waynesboro

02 :44 hrs
27.6 mi
109.79724 ft

This ride will take you through the amazing Shenandoah Valley. You will encounter a long gradual climb out of the city, which can be challenging for the beginner rider. After you pass the climb, there will be a gradual descent. There will be short stretches of busy streets with heavier traffic throughout the ride. Plan on rolling hills for long stretches.


Virginia, Rockbridge County

02 :02 hrs
20.5 mi
96.36255 ft

This is a good route for beginners. The roads are all paved and in good condition. The ride is considered an out and back excursion with the exception of the small loop in Goshen. It is located in what is considered the most scenic part of Virginia. The way home from Goshen is easier than the beginning of a ride.


Maryland, Washington County

02 :18 hrs
5.1 mi
347.89536 ft

This hike is located in Harpers Ferry National Historical Park and features a great deal of history, beautiful thick forests, a mountain ridge, stunning views, and wildlife. In 1783 Thomas Jefferson declared the confluence of the Shenandoah and Potomac Rivers to be “perhaps one of the most stupendous scenes in Nature.” You will hike up to the top of a mountain ridge with gorgeous scenery and make your way to two breathtaking view points overlooking the rivers. Be sure to visit Harpers Ferry and learn about the history of the area before you set off.


West Virginia, Jefferson County

03 :27 hrs
6.5 mi
62.382416 ft

The Chesapeake & Ohio Canal Towpath is a historic trail running 184.5 miles from Cumberland, Maryland to Washington, DC . It is relatively flat and is made of crushed stone and clay. This small section of the towpath begins in Harper's Ferry. The park represents over 1,000 years of history, including the arrival of the first successful American railroad, John Brown's attack on slavery, and the largest surrender of Federal troops during the Civil War. As the trail travels to Brunswick MD, it is very scenic and offers many wildlife encounters. A parking fee is required in Harper's Ferry.


Maryland, Potomac

01 :16 hrs
3.7 mi
19.7414 ft

This hike is located in the C & O Canal National Historic Park only 30 minutes away from the Capital Beltway. The trail is named for the rocky and steep terrain with an abundance of opportunities to scramble over rocks and among cliff edges to attain optimal views of the rugged landscape. You will hike along the Potomac River with stunning views throughout, including views of Mather Gorge and return along the C & O Canal, passing old canal locks and beautiful scenery on a path that is wide and flat.


Maryland, Travilah

01 :27 hrs
4.3 mi
17.8899 ft

This hike is located in the C & O Canal National Historic Park only 30 minutes away from the Capital Beltway. On this hike you will pass historic canal locks, some of which are still in use, beautiful water views, including the chute of Great Falls, and a wonderful, rocky landscape which provides stunning scenery. Great Falls is a beautiful waterfall with intense raging water through Mather Gorge. Later on the hike, there are calm water views on the canal downstream. You will find rich history in the park as you hike past the old canal locks, historic buildings, and take the guided tours available here.


West Virginia, Jefferson County

03 :16 hrs
7.2 mi
262.1057 ft

This trail travels a small section of the Appalachian trail, beginning at Harpers Ferry National Historic Park. The park represents over 1,000 years of history, including the arrival of the first successful American railroad, John Brown's attack on slavery, and the largest surrender of Federal troops during the Civil War. The trail passes many old buildings and ruins that have been preserved. Over 170 bird species as well as many mammal species are located in the park including, the southern flying squirrel and the bald eagle. The Appalachian and Loudoun Heights Trail travels through thick eastern deciduous forest, consisting of chestnut oak, tulip poplar and red maple. The trail leads to Split Rock Overlook, providing views of the town of Harpers Ferry as well as the confluence of the Shenandoah and Potomac River. National Park Service fee is required, fee envelopes provided at the parking lot. The park is open year-round from 9 a.m. to 5 p.m and closed some holidays.


Virginia, Greene County

04 :50 hrs
10.9 mi
388.90216 ft

This long and strenuous but popular section of the Appalachian Trail parallels Skyline Drive on its way north from Pinefield Gap to Swiftrun Gap. Black bear sightings are common in the lonely peaks of the northern Shenandoah, and there are views aplenty for hikers that wish to brave this day-long stretch of the AT as it slithers along the ridges. Be wary when crossing Skyline Drive, as this route crosses the road often; also, several brief spur trails lead to peaks like the Swiftrun Overlook, Bacon Hollow, and Hightop. Upon arrival at Swiftrun Gap, cross Skyline Drive and take the bridge across VA 33 to walk towards the parking area.


Virginia, Charlottesville

04 :04 hrs
9.2 mi
405.33295 ft

This arduous day hike follows the famous Riprap Trail in a loop around the incredible scenery of the southern portion of Shenandoah National Park. Descending through the forests of mountain laurel that cover the mountainside, the trail eventually comes to Wildcat Ridge as it switchbacks down into the valley. Turning right and following the Riprap Trail, the path follows the creek for many miles into Cold Spring Hollow. Ascending into the forests once more, hikers will marvel at the views from Calvary Rocks as they make their way across the quartz-studded ridge line. When the Riprap meets the Appalachian Trail, veer right on the AT as it parallels Skyline Drive on the way back to the parking area.

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