Jessup, Maryland

Looking for the best chillin 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 Chillin Spots in and near Jessup

  • Thurmont, Maryland

    Hike Catoctin Mountain

    4.5
    8.4 mi / 1370 ft gain
    Park at Catoctin Mountain Visitor Center. The hike starts at the end of the gravel parking lot across from the visitor center. This is definitely a popular hiking location, so come early on the weekends to guarantee a parking spot and to avoid the crowds. To start, take the right trail towards th...
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  • Graceham, Maryland

    Cunningham Falls via Lower Trail

    4.3
    1.04 mi / 156.17 ft gain
    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 Cree...
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