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Jessup, Maryland

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

Top Hiking Spots in and near Jessup

  • Thurmont, Maryland

    Hike Chimney Rock at Catoctin Mountain Park

    4.2
    5 mi / 600 ft gain
    Chimney Rock is the quintessential breathtaking view that makes a hike worthwhile. By parking at the most northeast parking lot on the trail map you are able to include the sweeping views of Thurmont Vista, and Wolf Rock on your way to Chimney Rock. Highly recommend visiting in the fall, and on w...
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  • Thurmont, Maryland

    Hike the Catoctin Mountain Extended Loop Trail

    4.5
    8.6 mi / 1696 ft gain
    This 8.6 mile loop trail in Catoctin Mountain Park is good for both hikers and trail runners. This loop is the larger loop in the park, comprised of Cunningham Falls, Hog Rock, Blue Ridge Summit, Thurmont Vista, Wolf Rock, and Chimney Rock. The trail gets a moderate rating because it's mostly roc...
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  • Smithsburg, Maryland

    Hike to Cunningham Falls

    4.2
    2.8 mi
    This 78-foot waterfall, among the largest in the state, is easily accessible by two short trails. Lower Trail (0.5 miles) leads directly to the falls, whereas Cliff Trail (0.75 miles) has slightly more difficult terrain and takes you to a viewing platform. To lengthen the adventure, Hunting Creek...
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