Outbound Collective logo

Poolesville, Maryland

Looking for the best hiking in Poolesville? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Poolesville. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Poolesville

  • Elkridge, Maryland

    Hike the Cascade Falls and Rootball Loop Trail

    4.7
    2.4 mi / 285 ft gain
    Park on the shoulder of Landing Drive (see map) to access the trailhead. This trail is open April-September. Dogs allowed on leash. 
    Read more
  • Owings Mills, Maryland

    Serpentine Trail

    4.5
    2.39 mi / 226 ft gain
    Park in the area off of Deer Park road to access the trail. Dogs are welcome on leash. Trail can get muddy in the spring, and there are some stream crossings. 
    Read more
  • Owings Mills, Maryland

    Soldiers Delight Loop

    4.7
    5.33 mi / 466 ft gain
    From Deer Park Road, parking is available at the nature center or the scenic overlook (about 100 yards up the road). I typically park at the overlook as this affords the ability to hike trails on either side of the road, and always finish the hike back at the car. From the parking area you are ju...
    Read more
  • Elkridge, Maryland

    Cascade Falls Loop

    3.0
    2.31 mi / 381 ft gain
    This hike is a great place to escape the city feel of Baltimore and disappear into the wilderness. Enter through the Avalon Area entrance. There is a cash fee to enter the park. Once you pass the front gate continue past the initial picnic area. Continue through the park to the Orange Grove Area...
    Read more
  • 7, Smithsburg, Maryland

    Hike to Devil's Racecourse on the Appalachian Trail

    4.5
    3 mi / 1500 ft gain
    Start your hike where the AT crosses Raven Rock Road (Maryland Route 491). This crossing is well-marked from both sides by large, yellow signs and blazed stakes. You will need to park on the side of the road, but the shoulder is wide and can accommodate a crowd.  The first half mile or so of this...
    Read more
  • Lorton, Virginia

    Woodmarsh Trail

    4.0
    2.83 mi / 154 ft gain
    Just at the entrance to Mason Neck State Park is the Woodmarsh Trail. The entire loop is about 3 miles. This is a pleasant easy hike that is relatively flat with no rocks to speak of. The trail wanders through a forest and passes by a large swamp along the Potomac River. There is one well built o...
    Read more
  • Sabillasville, Maryland

    Hike to High Rock on the Appalachian Trail

    4.0
    6 mi / 2000 ft gain
    Start your hike where the AT crosses Raven Rock Road (Maryland Route 491). This crossing is well-marked from both sides by large, yellow signs and blazed stakes. You will need to park on the side of the road, but the shoulder is wide and can accommodate a crowd.  The first half mile or so of this...
    Read more
  • Baltimore, Maryland

    Hike the Fort McHenry Trail

    3.5
    0.9 mi / 16 ft gain
    Park in the lot and head out either direction on this short loop trail. Trail can get crowded, so be prepared to share the space. 
    Read more
  • Cockeysville, Maryland

    Hike the Oregon Ridge Park Trail

    4.0
    4.02 mi / 475 ft gain
    Park in the lot as indicated on the map (see below). This trail is accessible year round, dog-friendly, and is great for families. 
    Read more
  • South River, Virginia

    Hike to Compton Peak

    5.0
    This unique hike on the Appalachian Trail in Shenandoah National Park is 2.4 miles round trip with an 835' elevation gain, and leads you to two viewpoints as well as a cool rock outcrop.Access this hike from the Compton Gap parking area (elevation 2,145') on the Skyline Drive at Mile 10.4. Cross ...
    Read more
  • Front Royal, Virginia

    Explore Skyline Drive In Winter

    4.5
    Skyline Drive is a winding highway that cuts straight through Shenandoah National Park. Being that we are in the south, you will find that the road is closed for the majority of the winter, and usually at the very mention of snow. The first few years of living here it was incredibly frustrating...
    Read more
  • Appalachian Trail, Virginia

    Hike North Mount Marshall in Shenandoah NP

    1 mi / 350 ft gain
    Park at the Mount Marshall parking area at ~MP 15.6 on the Skyline Drive.  From the back of the parking lot, take the white-blazed Appalachian Trail north for a short 0.4 miles to a large rock outcrop with views south.  After finished exploring this outcrop, continue on the AT for another 0.1 mil...
    Read more