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
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Oakland, Maryland
Hike the Herrington Manor/Swallow Falls Trail
5.011 mi / 25 ft gainI 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...Read more -
Oakland, Maryland
Hike the Swallow Falls Loop
4.71.1 mi / 125 ft gainThis 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).Read more -
Oakland, Maryland
Swallow Falls Canyon Trail
1.11 mi / 213 ft gainSwallow Falls Canyon Trail is a loop trail where you may see beautiful wildflowers located near Oakland, Maryland.Read more -
Oakland, Maryland
Rock Maze Trail
0.83 mi / 92 ft gainRock Maze Trail is an out-and-back trail where you may see beautiful wildflowers located near Oakland, Maryland.Read more -
Oakland, Maryland
Lostland Run Trail
7.25 mi / 755 ft gainLostland Run Trail is an out-and-back trail that takes you by a river located near Oakland, Maryland.Read more -
McHenry, Maryland
Red Trail to Green Trail Loop
7.43 mi / 942 ft gainRed Trail to Green Trail Loop is a loop trail that takes you through a nice forest located near McHenry, Maryland.Read more -
McHenry, Maryland
Red Trail Loop
3.66 mi / 387 ft gainRed Trail Loop is a loop trail that provides a good opportunity to view wildlife located near McHenry, Maryland.Read more -
Aurora, West Virginia
Cathedral to Giant Hemlock Trail Loop
2.5 mi / 381 ft gainCathedral to Giant Hemlock Trail Loop is a loop trail that provides a good opportunity to view wildlife located near Aurora, West Virginia.Read more -
25164 George Washington Highway, West Virginia
Hike the Cathedral Trail in Cathedral SP
5.01.1 mi / 0 ft gainCathedral 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...Read more -
Swanton, Maryland
Brant Mine Trail
2.51 mi / 269 ft gainBrant Mine Trail is an out-and-back trail where you may see beautiful wildflowers located near Swanton, Maryland.Read more -
Eglon, West Virginia
Hoye Crest (Backbone Mountain)
1.99 mi / 650 ft gainHoye Crest (Backbone Mountain) is an out-and-back trail that provides a good opportunity to view wildlife located near Eglon, West Virginia.Read more -
Swanton, Maryland
Hike the Big Savage Mountain Trail (Southern Terminus to High Rock)
11 mi / 1500 ft gainThis 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. ...Read more -
Friendsville, Maryland
Kendall Trail
10.33 mi / 804 ft gainKendall Trail is an out-and-back trail that takes you by a river located near Friendsville, Maryland.Read more -
Davis, West Virginia
Beaver Creek, White, and Camp 70 Road Trail Loop
2.04 mi / 135 ft gainBeaver Creek, White, and Camp 70 Road Trail Loop is a loop trail that takes you by a river located near Davis, West Virginia.Read more -
Davis, West Virginia
Pase Point via Dobbin House Trail
2.83 mi / 325 ft gainPase Point via Dobbin House Trail is an out-and-back trail that takes you through a nice forest located near Davis, West Virginia.Read more -
Davis, West Virginia
Camp at Blackwater Falls State Park
5.0Blackwater 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 ...Read more