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Oakland, Maryland

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

Top Hiking Spots in and near Oakland

  • Davis, West Virginia

    Dolly Sods Wilderness North Loop via Rocky Ridge Trail

    5.0
    12.78 mi / 1378 ft gain
    The hike begins at the "Dolly Sods Trailhead Parking" location easily found on Google Maps. The lot is big enough for about 6-8 vehicles. Begin walking at the end of the gravel parking lot/road for about 0.5 miles until you enter the Dolly Sods Wilderness Area in a small grassy field where sever...
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  • Davis, West Virginia

    Hike the Freeland Boardwalk Trail

    4.0
    0.4 mi / 0 ft gain
    A free entrance and parking area for about a half dozen cars off Freeland Road features this quick adventure for all ages. The Canaan Valley National Wildlife Refuge and Freeland Boardwalk offers a variety of wildlife and environments like Ponds, Wetlands, Forests, and a natural limestone spring....
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  • Salisbury, Pennsylvania

    Primitive Camp along Wolf Rocks Trail

    3.0
    1.5 mi / 50 ft gain
    This is a GREAT location for beginning backpackers with minimal backpacking rules, short trails and cell service. Although all trails (with a few exceptions found in this brochure -labeled as "Areas Closed to Camping") in the Forbes State forest allow primitive backpack camping (primitive backpac...
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  • Cabins, West Virginia

    Backpack the North Fork Mountain Trail & Chimney Top

    5.0
    24.7 mi
    One of my favorite hikes in West Virginia, since the whole ridge is full of views.  Backpacking the North Fork Mountain Trail is about 24.7 miles in total and a challenging hike but with relentless views. In my opinion, the best West Virginia has to offer. Summertime backpacking the whole the NFM...
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  • Davis, West Virginia

    Hike to Rohrbaugh Cliffs in Dolly Sods

    5 mi
    Rohrbaugh Cliffs is the social name given to the expansive views found along the Rohrbaugh Plains Trail.  This easy hike in the Dolly Sods Wilderness will take you to one of the best overlooks in the area.  For a longer or more challenging hike, connect this trail with one of the many others in t...
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  • Ohiopyle, Pennsylvania

    Explore Cucumber Falls

    4.3
    0.25 mi / 30 ft gain
    Just off Kentuck Road, at the southern end of Ohiopyle State Park, you arrive at Cucumber Falls' marked parking lot. Access to this lot is limited (about 20 cars). Most of the time you will be able to find a spot, but when not, parking on the side of the road is perfectly acceptable.Walking down ...
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  • Cabins, West Virginia

    Hike to Chimney Rock in the Monongahela National Forest

    4.7
    4.85 mi / 1319 ft gain
    Chimney Rock (also referred to as Chimney Top) is a hidden gem in the Monongahela National Forest that offers some of the best views in the state of West Virginia.  There are several trail options that pass this overlook, including a 24 mile point-to-point backpack of the North Fork Mountain Trai...
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  • Mill Run, Pennsylvania

    Explore Fallingwater

    4.8
    "Fallingwater is the name of a house built over a waterfall in southwest Pennsylvania. Frank Lloyd Wright, America’s most famous architect, designed the house for his clients, the Kaufmann family. Fallingwater was built between 1936 and 1939. It instantly became famous, and today it is a Natio...
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  • Mill Run, Pennsylvania

    Hike the Bear Run Nature Reserve Loop

    4.0
    8 mi
    Bear Run Nature Reserve features a number of trail loops that range from 1.7 miles in length to 11.9 miles.  By hiking overlapping trails, you can complete an 8 mile hike that passes by Paradise Overlook, which provides great views of the Youghiogheny River Gorge.  Start at the trailhead, which i...
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  • Dunbar, Pennsylvania

    Hike the Sugar Run Trail

    1.6 mi
    This trail connects Old Mitchell Trail to Johnathan Run Trail. It is a short but fun hike down to the falls. We parked by the helicopter landing field and the trail head was right by the entrance to the parking lot.The hike down to the falls was nice and easy, but coming back up was tough. The tr...
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  • Fairmont, West Virginia

    Rhododendron Trail and Rocky Trail Loop

    4.3
    3.82 mi / 738 ft gain
    A former lumber and gristmill community, Valley Falls State Park offers one of the most accessible--and massive--waterfalls in WV. Just a few dozen yards from the parking lot, you'll find the park's namesake (and probably a lot of people, engagement photoshoots, and just general mayhem). But if y...
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  • Fairmont, West Virginia

    Valley Falls via Rocky and Rhododendron Trail

    3.82 mi / 738 ft gain
    Valley Falls via Rocky and Rhododendron Trail is a loop trail that takes you by a waterfall located near Fairmont, West Virginia.
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  • Seneca Rocks, West Virginia

    Seneca Rocks Trail

    4.7
    3.12 mi / 784 ft gain
    Seneca Rocks is probably one of the best known landmarks in West Virginia. This iconic formation sits 900 feet above the North Fork River. I highly recommend anyone interested in taking a trip to West Virginia take some time to visit Seneca Rocks. These rock formations are really an amazing site....
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  • Seneca Rocks, West Virginia

    Camp at Yokum's Vacationland

    With warm weather, we couldn't wait to go camping so we drove a few miles south of us to Yokum's Vacationland to camp in a teepee. It was THE BEST! It was so cold and we forgot our air mattress pump so we ended up car camping but the whole adventure was so awesome. We were the only people camping...
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  • Seneca Rocks, West Virginia

    Climb Seneca Rocks

    5.0
    2.6 mi / 700 ft gain
    Park at the Seneca Rocks visitor parking spot located just off Mountaineer Drive. Take the trail directly across from the lot, cross the bridge over the stream, and follow the trail about one mile until you see a rock stair trail on your left side (Seneca Rocks side). Follow this rock stair trail...
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  • Mathias, West Virginia

    Hike Cranny Crow to Millers Rock Loop

    10.6 mi / 2100 ft gain
    This is a really good day hike to explore another one of the many fantastic state parks that West Virginia has to offer while avoiding some of the crowds that many of the popular ones have. The main feature of the park is the Cranny Crow Overlook which features views into two Virginia and three W...
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