Upperville, Virginia

Top Spots in and near Upperville

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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Delaplane, Virginia
Relax at Lake Thompson

Lake Thompson is a great spot for fishing, walking, or just exploring the area with your dog. I've never had a problem with parking, but you're unlikely to find yourself alone at the lake on a nice weekend day. Its a 10-acre lake, however, so you shouldn't have a problem carving out a little bit...
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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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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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Front Royal, Virginia
Snowshoe the AT in G.R. Thompson

3 mi

The 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! ...
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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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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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Aldie, Virginia
Relax at Aldie Park

Small park with nice walking trails, picnic tables, and a waterfall that cascades down from a dam. Its a wonderful place to take the family or just go for a breath of fresh air. Its also right near the downtown area of Aldie, which has a bakery, juice/smoothie shop, and other great shops to stop ...
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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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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 ...
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Front Royal, Virginia
Explore Skyline Caverns

Skyline Caverns is located right off Stonewall Jackson Highway with plenty of parking. The cave tour is about 60 minutes with little walking and minimal elevation gain. If you time it right you and your friends can get the whole tour to yourselves. The backstory the tour guide gives you, is inte...
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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...
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Waterford, Virginia
Hike the Historical Phillips Farm in Waterford

4.0

1 mi / 10 ft gain

This 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...
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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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Manassas, Virginia
Hike and Explore Bull Run Battlefield

4.3

1.2 mi

Located 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...
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