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Sharpsburg, Maryland

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

Top Hiking Spots in and near Sharpsburg

  • Thurmont, Maryland

    Hike the Catoctin Mountain Extended Loop Trail

    4.5
    8.6 mi / 1696 ft gain
    This 8.6 mile loop trail in Catoctin Mountain Park is good for both hikers and trail runners. This loop is the larger loop in the park, comprised of Cunningham Falls, Hog Rock, Blue Ridge Summit, Thurmont Vista, Wolf Rock, and Chimney Rock. The trail gets a moderate rating because it's mostly roc...
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  • 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...
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  • Cool Spring Path South Parking, Virginia

    Hike Cool Spring Path

    4.0
    2 mi / 70 ft gain
    The Cool Spring Path South is an old golf course that has been and still is in the process of being returned to its natural state by Shenandoah University. The paved paths from the golf course make this an easy hike for anyone. For those who may be in a wheelchair, this loop should be fully acces...
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  • Bluemont, Virginia

    Hike to Raven Rock

    4.3
    5 mi / 1000 ft gain
    Starting at a small parking lot right off of Route 7 (wuick right onto Pine Grove Road) this hike takes you North on the Appalachian Trail in a very hilly/rocky part of the trail. Expect to gain and lose 300 feet+ multiple times! It's about 2.5 miles each way so budget at least a few hours to go ...
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  • Bluemont, Virginia

    Hike to Bears Den Overlook

    4.4
    1.31 mi / 164 ft gain
    Bears Den is a collection of rocks and boulders that overlooks the Shenandoah Valley in northern Virginia, just off the Appalachian Trail. You have two options to access this overlook: park at the bottom of the mountain and hike up to the overlook via the trail, or drive to the top and access the...
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  • Dickerson, Maryland

    Hike the Sugarloaf Mountain Trail

    4.7
    6.05 mi / 1509 ft gain
    Park on Sugarloaf Mountain Drive (as indicated on the map below) to access the trail. It is open from March-November and is dog friendly. 
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  • Dickerson, Maryland

    Hike along the C&O Canal: Whites Ferry to Edwards Ferry

    5.0
    10 mi / 165 ft gain
    Park in the lot on Whites Ferry road and hop on the Chesapeake Ohio towpath. This is an out-and-back so you can make it as short as you want or up to 10 miles. Great for familes and dog friendly!
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  • Leesburg, Virginia

    Hike the Red Rock Wilderness Overlook Loop

    5.0
    1.2 mi / 100 ft gain
    Red Rock Wilderness Overlook provides 60+ acres of trails to explore right in Leesburg, Virginia. The site is home to some ruins and buildings from the late 1800's and is a wonderful spot for picnics, hiking, trail running, and geocaching.The preferable loop is to take the trail that leads straig...
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  • Bluemont, Virginia

    Hike to Hollow Brook Falls

    4.3
    2 mi / 300 ft gain
    This hike will start on the Appalachian Trail and will take you to a beautiful set of falls.  When you arrive at the location you will see numerous spots along the side of the road to park. You'll need to look for the white blaze for the Appalachian Trail (it will head up from the parking area). ...
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  • Boyds, Maryland

    Hike or Bike the Hoyles Mill Trail

    9.16 mi / 390 ft gain
    Park on Clarksburg Road (see map) and head onto the marked trail. It can get muddy at times so pack accordingly. Great for kids, and dog friendly too. 
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  • Boyds, Maryland

    Black Hill Regional Park Loop

    5.0
    2.78 mi / 312 ft gain
    The Black Hill Regional Park has 1300 acres of oak forests that have views of the Little Seneca Lake. This lake offers a place for visitors to canoe and stand up paddle board.  This trail is open to hiking and mountain biking. In addition, dogs are welcome to use the trail but must be on leash a...
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  • Marshall, Virginia

    Hike to the Piedmont Overlook

    5.0
    0.61 mi / 400 ft gain
    In just a .61 mile trail, Piedmont Overlook has so much to offer in terms of views and although it is fairly steep, anyone can do it!  After arriving at Sky Meadows State Park start heading up to the white park office building, this is where the trail begins. To get to the trail head follow Bosto...
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  • Sky Meadows State Park, Virginia

    Camp at Sky Meadows State Park

    5.0
    2 mi
    Camping at Sky Meadows State Park is a great location to backpack with young kids or if you are new to backpacking. The campground has 18 primitive walk-in campsites located 1.03 miles from the overnight parking lot at the park entrance. Reservations can be made online. After checking-in and park...
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  • Montgomery Village, Maryland

    Hike the Seneca Creek Greenway Trail Upper Section

    5.0
    14.86 mi / 836 ft gain
    Park in the lot off of Watkins Mill Road to access the trail. This hike is dog friendly and is accessible from March until November. 
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  • Boyce, Virginia

    Trail Run the AT in the G.R. Thompson

    7 mi / 900 ft gain
    Take Fire Trail Road and start your run at the parking area (labeled in the map). The trail puts you directly onto the AT, where you will turn right (southbound) to start the run (or hike). You'll stay on the AT for roughly 3.5 miles down to the Trillium Trail Parking area. At that point, turn ar...
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  • Sterling, Virginia

    Washington & Old Dominion Trail and Broadlands Ramble

    5.0
    19.55 mi / 863 ft gain
    Washington & Old Dominion Trail and Broadlands Ramble is a point-to-point trail where you may see local wildlife located near Ashburn, Virginia.
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