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The Best Hiking in Oakland

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

  • Oakland, Maryland

    Hike the Herrington Manor/Swallow Falls Trail

    5.0
    11 mi / 25 ft gain
    I began my adventure at the trailhead in Herrington Manor State Park. The parking lot was empty and the trail was very easy to access. From start to finish this trail varies in the width of its path. For the first mile I had a lot of foot room, but as I went deeper into the forest, the trail turn...
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  • Oakland, Maryland

    Hike the Swallow Falls Loop

    4.7
    1.1 mi / 125 ft gain
    This park has plenty to do—forest hiking, swimming at Herrington Manor, and camping—but the main attraction, unsurprisingly, is Swallow Falls. The Swallow Falls Canyon Trail (1.1 miles) follows Muddy Creek and features a number of other falls, including Muddy Creek Falls (53 ft).
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  • Oakland, Maryland

    Swallow Falls Canyon Trail

    1.11 mi / 213 ft gain
    Swallow Falls Canyon Trail is a loop trail where you may see beautiful wildflowers located near Oakland, Maryland.
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  • Oakland, Maryland

    Rock Maze Trail

    0.83 mi / 92 ft gain
    Rock Maze Trail is an out-and-back trail where you may see beautiful wildflowers located near Oakland, Maryland.
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  • Oakland, Maryland

    Lostland Run Trail

    7.25 mi / 755 ft gain
    Lostland Run Trail is an out-and-back trail that takes you by a river located near Oakland, Maryland.
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  • McHenry, Maryland

    Red Trail to Green Trail Loop

    7.43 mi / 942 ft gain
    Red Trail to Green Trail Loop is a loop trail that takes you through a nice forest located near McHenry, Maryland.
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  • McHenry, Maryland

    Red Trail Loop

    3.66 mi / 387 ft gain
    Red Trail Loop is a loop trail that provides a good opportunity to view wildlife located near McHenry, Maryland.
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  • Aurora, West Virginia

    Cathedral to Giant Hemlock Trail Loop

    2.5 mi / 381 ft gain
    Cathedral to Giant Hemlock Trail Loop is a loop trail that provides a good opportunity to view wildlife located near Aurora, West Virginia.
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  • 25164 George Washington Highway, West Virginia

    Hike the Cathedral Trail in Cathedral SP

    5.0
    1.1 mi / 0 ft gain
    Cathedral Trail is a part of Cathedral State Park located east of Aurora, WV. Cathedral State Park was originally the site of Brookside Resort which attracted visitors from Washington D.C. and Baltimore, MD due to it’s cool clean air and natural beauty. The land was purchased in 1922 by Mr. Brans...
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  • Swanton, Maryland

    Brant Mine Trail

    2.51 mi / 269 ft gain
    Brant Mine Trail is an out-and-back trail where you may see beautiful wildflowers located near Swanton, Maryland.
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  • Eglon, West Virginia

    Hoye Crest (Backbone Mountain)

    1.99 mi / 650 ft gain
    Hoye Crest (Backbone Mountain) is an out-and-back trail that provides a good opportunity to view wildlife located near Eglon, West Virginia.
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  • Swanton, Maryland

    Hike the Big Savage Mountain Trail (Southern Terminus to High Rock)

    11 mi / 1500 ft gain
    This is not a casual hike; it is one which should be taken taken seriously. However, it will be an enjoyable experience for anyone with the resolve to face the early 1,500 ft. climb in elevation, as well the ascent of a slightly dodgy (but still structurally sound) mid-20th century fire tower.   ...
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  • Friendsville, Maryland

    Kendall Trail

    10.33 mi / 804 ft gain
    Kendall Trail is an out-and-back trail that takes you by a river located near Friendsville, Maryland.
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  • Davis, West Virginia

    Beaver Creek, White, and Camp 70 Road Trail Loop

    2.04 mi / 135 ft gain
    Beaver Creek, White, and Camp 70 Road Trail Loop is a loop trail that takes you by a river located near Davis, West Virginia.
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  • Davis, West Virginia

    Pase Point via Dobbin House Trail

    2.83 mi / 325 ft gain
    Pase Point via Dobbin House Trail is an out-and-back trail that takes you through a nice forest located near Davis, West Virginia.
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  • Davis, West Virginia

    Camp at Blackwater Falls State Park

    5.0
    Blackwater Falls State Park is one of 36 state parks in West Virginia and is located just north of the Canaan Valley less than two miles from Davis, WV.  Blackwater Falls State Park has over 2,000 acres, making it a great place to camp while you explore the beautiful area.  The campground has 65 ...
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