Best Trail Running in Maryland

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

1

Virginia, Augusta County

09 :23 hrs
25.5 mi
844.0032 ft
Extreme

The renowned Wild Oak Loop is perhaps the most popular backpacking trip in the George Washington National Forest, or at least a close second to commensurate sections of the Appalachian Trail. It can also be hiked in smaller portions, as many hikers choose to split the trail into one-way sections that go between the network of roads that intersect the trail. Alternatively, local trail runners have made this loop a destination for runners from around the region. The loop has so much to offer, including ridgeline views of Todd Lake and summit vistas from Little Bald Knob. As the path veers southwest, continuing along the White Oak Trail, numerous verdant deciduous forests await to enclose the avid runner in their shady embrace. Returning along the Hankey Mountain Trail (and the summit of this peak) runners will be rewarded with views of Elkhorn Lake and Staunton Dam, even a brief stint along the edge of the North River Gorge before returning to the parking area.

2

Maryland, Anne Arundel County

03 :06 hrs
10.5 mi
35.884323 ft
Expert

The Patuxent Research Refuge is the Nation’s only National Wildlife Refuge established to support wildlife research. The refuge is divided into three areas and this, the North Tract, offers hunting, fishing, wildlife observation, trails, and many interpretive programs. This route is especially popular with runners and hikers and is mostly on dirt or gravel roads and some forest trails. There is a spur trail that leads to the picturesque Reeves Pond. There are some ups and downs to challenge runners and there are shorter routes available as well.

3

Virginia, Madison County

03 :08 hrs
6.3 mi
664.1326 ft
Hard

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.

4

Virginia, Greene County

04 :50 hrs
10.9 mi
388.90216 ft
Expert

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.

5

Virginia, Charlottesville

04 :04 hrs
9.2 mi
405.33295 ft
Expert

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.

6

Virginia, Greene County

04 :55 hrs
11.3 mi
704.07654 ft
Expert

This strenuous but rewarding river loop begins wending its way down into the valley on the Slaughter Trail. Traveling through pine and deciduous forests on old logging trails, eventually the path will come to the Conway River. Make a hard left onto Conway River Road and parallel the water all the way through the gulch. After a lengthy stretch of walking and several rockhopping fords, the trail will begin ascending back up to the ridgeline. When the trail reaches Skyline Drive, make a hard left on the Appalachian Trail as it parallels the road. Make a brief detour to the left to scramble up the side of Bearfence Mountain for incredible views in all directions before heading back to the parking area.

7

Virginia, Warren County

04 :28 hrs
10 mi
681.79126 ft
Expert

This beautiful and popular loop hike begins by crossing Skyline Drive and coming to an overlook on Marshall Mountain. The path then follows the Appalachian trail to the summit of Hogsback Mountain, which allows stunning and uninterrupted views of the Massanutten region to the north. Descending along the Hogsback ridge, veer right along Jinney Gray Road which begins curving down the slope on its way to the Little Devils Stairs Trail. Solemn rock monoliths and roaring waterfalls await hikers as they descend through the valley carved by Keyser Run among hidden pools and groves of sapling maples. Upon reaching the bottom of the creek, make a right on the Keyser Run Fire Road as it cuts a wide swath through the open woods and arrives at Bolen Cemetery (with gravestones dating back to the Civil War). When the Keyser Run Fire Road merges with the Sugarloaf Trail, take this back towards Marshall Mountain and the parking area.

8

Virginia, Madison County

03 :42 hrs
8.3 mi
369.95813 ft
Expert

Beginning from the Fishers Gap Overlook, which offers many wide-ranging views of its own, this route begins following the Skyland-Big Meadows Horse Trail. This well-trodden path passes through deciduous forests and open meadows on its way through the ridges that run along the edge of Skyline Drive. Crossing the road, take the Lower Hawksbill Trail to ascend to the summit of the highest peak in Shenandoah: Hawksbill Mountain. From the observation platform hikers can look for miles in every direction and take in numerous views of the Blue Ridge topography. After descending from the peak, take the Appalachian Trail on its wandering course back to Fisher’s Gap.

9

Virginia, Page County

02 :05 hrs
5.9 mi
503.7266 ft
Expert

Beginning from the Elkwallow Trailhead, veer left towards the Knob Mountain Trail and then another left to walk along the ridge line of Knob Mountain. After a long but vista-filled hike, summit at the peak of Knob Mountain and then continue along the ridge trail as it switchbacks down into Jeremy’s Run. As the trail parallels the water and makes several fords of the river itself, keep an eye out for waterfalls and hesitant wildlife that frequent this region (including black bears!). After exploring the hidden grottoes and watery hollows of Jeremy’s Run, begin ascending back along the gradually disappearing creek towards the Elkwallow Trailhead.

10

Virginia, Madison County

03 :32 hrs
7.4 mi
685.5984 ft
Expert

Perhaps one of the most popular loop hikes in Shenandoah, this route begins from the trailhead on Weakley Hollow Road and proceeds to the right along the White Oak Canyon Trail. Running parallel to the Robinson River, hikers will see numerous waterfalls, cascades, rock formations, and hidden pools. When the path intersects with Skyland-Big Meadows Horse Trail, take a hard left and continue a steep upward ascent. This path follows several switchbacks until it comes near to Skyline Drive, and then makes another left onto the Cedar Run Trail. The descent through Cedar Run is similarly stunning, offering waterfalls and grottoes along the creek as it wends through the valley back toward the parking area.

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