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Upperville, Virginia

Top Spots in and near Upperville

  • Manassas, Virginia

    Trail Run at Bull Run

    5.0
    4 mi
    Great spot for a run! Very accessible for those in the DC region.  A good starting point is the Henry Hill Visitor Center. If you want to avoid any crowds, start early.  From the Henry Hill Visitor Center, you can't really go wrong (as far as direction is concerned) since most trails can be linke...
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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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  • 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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  • 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...
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  • Harpers Ferry, West Virginia

    Hike Weverton Cliffs Overlook from Harpers Ferry

    5.0
    8.2 mi / 925 ft gain
    Parking and trail head: Park at the Harpers Ferry Visitors Center for $10 (171 Shoreline Dr, Bolivar, WV 25425) and take the shuttle a mile and a half to lower town (free).  Walk straight from the shuttle to the large bridge. Cross the bridge to hop on the C&O canal trail. This is the point w...
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  • Harpers Ferry, West Virginia

    Hike Maryland Heights via Harpers Ferry

    4.5
    4.2 mi / 800 ft gain
    Parking and trail head: Park at the Harpers Ferry Visitors Center for $10 (171 Shoreline Dr, Bolivar, WV 25425) and take the shuttle a mile and a half to lower town (free).  Walk straight from the shuttle to the large bridge. Cross the bridge and take a left on the C&O Canal trail. You will s...
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  • Bentonville, Virginia

    Photograph Range View Overlook

    5.0
    Range View Overlook in Shenandoah National Park is an amazing spot to watch the sunrise and sunset where the Blue Ridge Mountains meet the rolling hills. Range View Overlook has views of Jenkins Mountain to the south, Pignet Mountain and Mary’s Rock to the southwest, and Hogback Mountain to the w...
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  • Purcellville, Virginia

    Explore Potomac Wayside Park

    4.0
    0.25 mi / 75 ft gain
    This is a small park along route 340 in Purcellville, Virginia near Harper's Ferry. After you have parked, look for the park sign which will be a few feet behind you. There is a trail that will take you down to the bottom of the waterfall and eventually to the Potomac River. There is also a trail...
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  • Bentonville, Virginia

    Hike the Shenandoah River State Park Loop

    5.0
    8 mi / 650 ft gain
    Shenandoah River State Park is located in the heart of the Shenandoah Valley.  The park is full of well-maintained trails great for hiking and mountain biking.  The trails both parallel the banks of the river as it snakes through the Shenandoah Valley and through the rolling hills, which provides...
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  • Knoxville, Maryland

    Hike to Maryland Heights

    4.8
    2.8 mi / 900 ft gain
    Maryland Heights is at the convergence of Maryland, West Virginia and Virginia, as well as the Potomac and Shenandoah Rivers. The Appalachian Trail and C&O Canal Towpath are also easily accessible from the trailhead parking lot. The parking lot holds about 16 cars and is between Locks 33 and ...
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  • Knoxville, Maryland

    Hike Maryland Heights Trail Loop

    5.3 mi / 1600 ft gain
    Learn Civil War history as you hike through forts and read signs about the war.  Enjoy beautiful lookouts, including one with a great view of Harpers Ferry.  The 5.3 mile hike is relatively easy and offers an interesting opportunity to learn history in one of the most important historical areas i...
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  • Knoxville, Maryland

    Hike the AT to Weverton Cliffs

    4.9
    3 mi / 1500 ft gain
    The trailhead is located right off Weverton Cliff's Road in Knoxville, Maryland. Park at a Park and Ride on the right side of the road, then walk right out of the parking lot down Weverton Cliff's Road until you see the white blazes of the Appalachian Trail. Follow that trail for 1.5 miles along ...
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  • Knoxville, Maryland

    Explore Point of Rocks/ Potomac River Overlook

    4.0
    0.2 mi / 95 ft gain
    Park at the Chesapeake and Ohio Canal parking lot. Walk to the US 15 and cross the road. Trail is not marked, though its faint traces can be detected as you continue on. GPS is recommended. Enjoy the overlook and when you're ready to go back, retrace your steps. 
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  • Rileyville, Virginia

    Hike to Overall Run Falls

    5.0
    6.1 mi / 1700 ft gain
    Start at the Hogback parking lot at MP 21.1 on the Skyline Drive. Take the Appalachian Trail south for 0.8 miles, and turn right onto the Tuscarora-Overall Run Trail. After 0.5 miles you will come to another intersection-keep right to stay on the Tuscarora-Overall Run Trail. A final intersection...
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  • Washington, Virginia

    Hike Little Devil Stairs

    4.7
    5.5 mi / 1480 ft gain
    This hike starts with an immediate stream crossing -- how wet your feet get depends on the water level but bring an extra pair of socks! The first mile consists of a typical Shenandoah hike -- uphill on a dirt path and along a stream. But soon you reach the base of Little Devil Stairs. This po...
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  • Rileyville, Virginia

    Backpack Jeremy's Run Trail, Shenandoah NP

    3.3
    10 mi
    This hike is best done as a two-day, one-night backpacking trip, however it can be done as a day hike if you don't wish to backpack.Jeremy’s Run is a beautifully forested 10 mile roundtrip hike with numerous stream-crossing. The trailhead starts at the Elkwallow Picnic area, at about mile 24 of S...
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