Upperville, Virginia
Looking for the best hiking in Upperville? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Upperville. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Upperville
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Marshall, Virginia
Hike to the Piedmont Overlook
5.00.61 mi / 400 ft gainIn 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...Read more -
Sky Meadows State Park, Virginia
Camp at Sky Meadows State Park
5.02 miCamping 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...Read more -
Bluemont, Virginia
Hike to Hollow Brook Falls
4.32 mi / 300 ft gainThis 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). ...Read more -
Boyce, Virginia
Trail Run the AT in the G.R. Thompson
7 mi / 900 ft gainTake 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...Read more -
Front Royal, Virginia
Snowshoe the AT in G.R. Thompson
3 miThe G.R. Thompson is a piece of public land in Linden, VA, thats primarily used by hunters. The Appalachian Trail runs right through this section and visiting during a fresh snowfall can make for a great adventure. Only 60 minutes drive from greater Washington DC area, this is an easy adventure! ...Read more -
Bluemont, Virginia
Hike to Bears Den Overlook
4.41.31 mi / 164 ft gainBears 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...Read more -
Bluemont, Virginia
Hike to Raven Rock
4.35 mi / 1000 ft gainStarting 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 ...Read more -
Cool Spring Path South Parking, Virginia
Hike Cool Spring Path
4.02 mi / 70 ft gainThe 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...Read more -
South River, Virginia
Hike to Compton Peak
5.0This 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
4.5Skyline 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 -
Waterford, Virginia
Hike the Historical Phillips Farm in Waterford
4.01 mi / 10 ft gainThis leisurely hike starts at the Old Mill at Waterford in Waterford, Virginia. You can find parking along the side of the road right near the mill. As you walk down and past the mill you'll see a fence and the beginning of the trail. This is a short, 1 mile hike and almost completely flat. If y...Read more -
Leesburg, Virginia
Hike the Red Rock Wilderness Overlook Loop
5.01.2 mi / 100 ft gainRed 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...Read more -
Manassas, Virginia
Hike and Explore Bull Run Battlefield
4.31.2 miLocated about 40 minutes from D.C. just off I-66 in Manassas, VA. Henry Hill is the starting point and headquarters that can lead you to multiple trails ranging from 1-5 miles depending on the route you choose here. Ample parking at HQ as well as clean restrooms. Tours are available here. Rolling...Read more -
Manassas, Virginia
Trail Run at Bull Run
5.04 miGreat 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...Read more -
Dickerson, Maryland
Hike along the C&O Canal: Whites Ferry to Edwards Ferry
5.010 mi / 165 ft gainPark 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!Read more -
Sterling, Virginia
Washington & Old Dominion Trail and Broadlands Ramble
5.019.55 mi / 863 ft gainWashington & Old Dominion Trail and Broadlands Ramble is a point-to-point trail where you may see local wildlife located near Ashburn, Virginia.Read more