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Upperville, Virginia

Top Spots in and near Upperville

  • Luray, Virginia

    Hike Robertson Mountain in Shenandoah NP

    6 mi / 1200 ft gain
    Robertson Mountain is often overshadowed by the nearby Old Rag Mountain, but standing 5 feet taller than Old Rag, this hike offers seclusion and gorgeous views to the south.  Starting from the Limberlost Trailhead parking lot at MP 43 on the Skyline Drive, take the chained off Old Rag Fire Road. ...
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  • Wardensville, West Virginia

    White Rocks Loop, George Washington NF

    4.5
    9.26 mi / 1690 ft gain
    The trail begins near the upper parking area next to a closed gate. If you park in the lower parking area, you'll have to walk about .3 miles up the road to get to this gate. Start out on the forest service (FS) orange-blazed trail, following it for about a quarter mile. From there head onto Old...
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  • Luray, Virginia

    Explore the Luray Caverns

    4.8
    The caverns are located in the town of Luray, which is in the Shenandoah Valley of northwest Virginia. They can only be explored by tour, and at first I was hesitant to pay the $26 entrance fee, but after an hour-long tour that blew my mind, I had absolutely no regrets. The tour includes about 30...
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  • Syria, Virginia

    White Oak Canyon Cedar Run Loop

    4.0
    7.67 mi / 2257 ft gain
    This route combines Cedar Run Falls and White Oak Canyon Trail (one of the more popular hikes in SNP, with separate adventures detailing those hikes). Parking is easy, but gets very crowded due to the popularity of White Oak Canyon (WOC). When starting from the parking area/Shenandoah ranger stat...
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  • Syria, Virginia

    Hike Cedar Run Falls Trail

    4.7
    2.6 mi / 1000 ft gain
    Cedar Run Falls is located in the central district of Shenandoah National Park.  This is a pretty waterfall that flows into a deep swimming hole.  There are two ways to get to the Cedar Run Waterfall: from the top of the mountain off of Skyline Drive and from the bottom of the mountain off of Wea...
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  • Syria, Virginia

    Fly Fish on the Robinson River

    5.0
    6 mi / 2000 ft gain
    There are two sections that you can fish on the Robinson River. The first section is about 15 minutes away from the trailhead of White Oak Canyon. The river is on the right side of the road and you can see where it has bee stocked from the white diamonds on the trees on the side of the road. This...
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  • Arlington, Virginia

    Fish the Potomac River in Arlington

    Parking along 36th Road in Arlington, VA, head down the path on the Gulf Branch Trail. Walk northeast for roughly a quarter mile, where you will intersect with the Potomac River. Find a spot along the sand, cast out, and watch the catfish bite! Chicken liver seems to work well.  Don't forget to h...
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  • Stanley, Virginia

    Hawksbill Mountain Summit

    4.8
    1.54 mi / 669 ft gain
    A hike to the summit of Hawksbill Mountain will not only put you at the highest point in Shenandoah National Park (4050'), but you'll have a 270 degree view perfect for a sunset. This moderate hike is located at MP 45.6 on the Skyline Drive in Shenandoah National Park, so you'll have to pay a $2...
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  • Stanley, Virginia

    Lower Hawksbill to Salamander to Appalachian Trail Loop

    2.68 mi / 666 ft gain
    This is one of 2 trails that will take you to the summit of Hawksbill Mountain. The other is the Upper Hawksbill Trail (which I also wrote an adventure about!). This trail is a combination of the Lower Hawksbill Trail, the AT, and the Salamander Trail. The parking are area for this hike is at mi...
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  • Myersville, Maryland

    Hike to Annapolis Rock and Black Rock Cliff

    4.4
    8 mi / 840 ft gain
    Hike along the Appalachian Trail as it passes through South Mountain State Park, taking you to a number of very scenic lookout spots.From the parking area, take the connector trail a short distance until you see blue blazes on the left – these will lead you to the Appalachian Trail (white blazes)...
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  • Luray, Virginia

    Upper Hawksbill Trail

    2.09 mi / 482 ft gain
    The trailhead has a small parking area at mile marker 46.7 on Skyline Drive, just past the Old Rag overlook (on the opposite side of the road) if you're driving south. The hike is a 2-mile out-and-back that takes you right to the summit. The first ~2/3 of it is relatively flat and very easy walk...
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  • Derwood, Maryland

    Hike, Bike, or Run the Lakeside Trail and Muncaster Mill Trail

    4.5
    3.41 mi / 196 ft gain
    Park at the Meadowside Nature Center to Access the trailhead. This is a 3.4 mile loop with opportunities for birding and observing wildlife. Dogs are welcome on leash. 
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  • Stanley, Virginia

    Photograph Spilter Knoll Overlook

    5.0
    The Spitler Knoll is one of 72 overlooks for people to enjoy as they travel through Shenandoah National Park along Skyline Drive.  Skyline Drive is the road that winds through the heart of Shenandoah National Park, starting at Front Royal in the north and ending at Rockfish Gap in the south. This...
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  • Washington, District of Columbia

    Hike the Soapstone Valley Trail

    4.0
    2 mi
    This is an out-and-back trail that starts and ends on different roads, but you will have better luck parking on Albemarle Street NW (where I have indicated the trailhead is on the map). This is a long street with plenty of street parking, just pay attention to the signs to see how long you can le...
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  • Arlington, Virginia

    Bike the Mt. Vernon Trail

    5.0
    14 mi
    Start your ride at the Teddy Roosevelt Island parking area and head southbound towards Mt. Vernon. You'll be riding next to the Potomac the entire time, with great views of the National Monument, Lincoln Memorial, Jefferson Memorial, and the Memorial Bridge. The ride is as long as you want to mak...
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  • Arlington, Virginia

    Hike Theodore Roosevelt Island

    4.3
    2 mi
    It seems only fitting that the president who gave us our national parks would have one all to his own.  Located on the edge of Washington D.C., Theodore Roosevelt Island offers a glimpse of what the city may have looked like before the politicians, before the marble buildings, before the traffic-...
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