Derwood, Maryland

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

Top Hiking Spots in and near Derwood

  • 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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  • 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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  • 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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  • Edgemere, Maryland

    Hike the Black Marsh Trail at North Point State Park

    2.5 mi
    First, a few disclaimers: The parking lot may be "at capacity" if you choose to visit the park in the summer. Do not despair; there is an auxiliary lot of sorts just near the gate.The park may be "full" but chances are you'll have the trails to yourself. Most people are here to hang in the design...
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  • Sabillasville, Maryland

    Camp at the Adirondack Shelters in Catoctin Mountain Park

    5.0
    4 mi / 1200 ft gain
    For outdoor enthusiasts, Maryland is an ideal place to live. Between the mountains and the Bay--and the rivers, bike paths, and trails along the way--we couldn't ask for much more. But if we were feeling greedy, we would probably ask for additional backpacking options, right? Of course, there are...
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  • 7, Smithsburg, Maryland

    Hike to Devil's Racecourse on the Appalachian Trail

    4.5
    3 mi / 1500 ft gain
    Start your hike where the AT crosses Raven Rock Road (Maryland Route 491). This crossing is well-marked from both sides by large, yellow signs and blazed stakes. You will need to park on the side of the road, but the shoulder is wide and can accommodate a crowd.  The first half mile or so of this...
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  • Parkton, Maryland

    Hike the Gunpowder Falls North and South Loop Trail

    5.0
    13.3 mi / 1180 ft gain
    Park in the lot on Bunker Hill Road and then continue a short ways to the trailhead (see map). There are no bridges for crossing the water so be prepared to pick your way across. 
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  • Marshall, Virginia

    Hike to the Piedmont Overlook

    5.0
    0.61 mi / 400 ft gain
    In just a .61 mile trail, Piedmont Overlook has so much to offer in terms of views and although it is fairly steep, anyone can do it!  After arriving at Sky Meadows State Park start heading up to the white park office building, this is where the trail begins. To get to the trail head follow Bosto...
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  • Sky Meadows State Park, Virginia

    Camp at Sky Meadows State Park

    5.0
    2 mi
    Camping at Sky Meadows State Park is a great location to backpack with young kids or if you are new to backpacking. The campground has 18 primitive walk-in campsites located 1.03 miles from the overnight parking lot at the park entrance. Reservations can be made online. After checking-in and park...
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  • Sabillasville, Maryland

    Hike to High Rock on the Appalachian Trail

    3.8
    6 mi / 2000 ft gain
    Start your hike where the AT crosses Raven Rock Road (Maryland Route 491). This crossing is well-marked from both sides by large, yellow signs and blazed stakes. You will need to park on the side of the road, but the shoulder is wide and can accommodate a crowd.  The first half mile or so of this...
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  • Freeland, Maryland

    Hike Hemlock Gorge

    5.0
    3.5 mi / 300 ft gain
    This is one of Baltimore's little known gems. The area contains an ecosystem which is essentially non-existent outside of the Appalachian mountain regions. It has also been seemingly under-appreciated and abused by locals. I am trusting that the Outbound Collective community will do its part to e...
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  • Baltimore, Maryland

    Vernal Pond & Brinkmans Trail Loop

    5.0
    2.67 mi / 188.98 ft gain
    Marshy Point Nature Center is 25 minutes northeast of Baltimore in Middle River, Maryland. Convenient from I-95 with lots of parking and miles of interconnected trails, it's a perfect spot for a quick hike or an all-day excursion.  The trails are mostly within the 1-2 mile range, but you can com...
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  • Boyce, Virginia

    Trail Run the AT in the G.R. Thompson

    7 mi / 900 ft gain
    Take Fire Trail Road and start your run at the parking area (labeled in the map). The trail puts you directly onto the AT, where you will turn right (southbound) to start the run (or hike). You'll stay on the AT for roughly 3.5 miles down to the Trillium Trail Parking area. At that point, turn ar...
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  • Kingsville, Maryland

    Jerusalem Village Trail & Jericho Covered Bridge Trail

    2.98 mi / 318 ft gain
    This is a moderately rated hike that features a river and quite a few hilly sections. The trail is known to be rather muddy, so be sure to wear appropriate waterproof footwear. Note that some sections of the trail are not well marked. You may want to review a map before embarking. There is park...
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