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

  • North East, Maryland

    Hike the White Banks Trail at Elk Neck SP

    5.0
    6 mi
    Most people visit Elk Neck to photograph the lighthouse, or access to the Bay (the throttle of speed boats is never far), but don't miss out on the trails. The three mile out-and-back White Banks Trail offers crazy-beautiful views of the Chesapeake as well as a moderately difficult workout. Park ...
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  • Thurmont, Maryland

    Cat Rock via Old Misery Trail

    3.0
    2.89 mi / 797 ft gain
    The best place to park is on Catoctin Hollow Road in the parking lot that's on the same side of the road as the lake. It's not a huge lot but we were here mid-summer around 10 am and found a spot easily. The trailhead is on the other side of the street from this parking lot; there is a sign letti...
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  • 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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  • Thurmont, Maryland

    Hike Chimney Rock at Catoctin Mountain Park

    4.4
    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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  • 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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