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Poughkeepsie, New York

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

Top Hiking Spots in and near Poughkeepsie

  • Elka Park, New York

    Hike to Plattekill Falls

    0.5 mi / 137 ft gain
    Just outside of Elka Park, New York, Plattekill Falls is accessible from Albany and New York City alike. This is a great hike for families and all skill levels. The falls are spectacular year-round, but the best time to visit is in the spring.  From the trailhead, walk left past the red house unt...
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  • Elka Park, New York

    Hike to Huckleberry Point

    4.5
    4.5 mi / 644 ft gain
    This is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...
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  • Elka Park, New York

    Backpack the Eastern Half of Devil's Path in the Catskill Mountains

    5.0
    14 mi / 3900 ft gain
    The Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...
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  • Elka Park, New York

    Backpack Devil's Path in the Catskills

    24.2 mi / 9000 ft gain
    Devil's Path is roughly more than 24 miles long, althought it feels like an eternity of milage. Going thru the summits of Indian head, Twin, Sugarloaf, Plateau, Hunter, and Westkill Mountains.Its brutal. Its painful, Its unique. Be prepared for anything and everything. You will encounter wild lif...
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  • Elka Park, New York

    Hike Indian Head Summit via Jimmy Dolan Notch Overlook

    4.9 mi / 1512 ft gain
    The view from the summit of this hike is incredible. Bring a sack lunch and a camera - you'll want to stay for a while! This trail is open for use year-round and provides great snowshoeing in the winter and fabulous wildflowers in the spring and summer. This is also a great location for birding!
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  • Elka Park, New York

    Hike Twin Mountain

    6 mi / 1586 ft gain
    The DEC Parking lot, is located at the very end of a dead end, along Prediger Rd. Start at the trail head to the right of the trail kiosk and sign in sheet. The trail starts out very easy going as you approach the base of Twin. At mile 0.25, you’ll hit a junction where you’ll turn RIGHT towards T...
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  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
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  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    7.5 mi / 1174 ft gain
    There are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road.  I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things.  For the most part the hike is flat but at some parts it c...
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  • Phoenicia, New York

    Hike Mt. Wittenberg

    4.3
    Looking for a great day hike in the Catskill region of NY? Then you should definitely look into and consider tackling Mt. Wittenberg then. A challenging climb up but a very rewarding summit view.Starting at Woodland Valley Campgrounds visitor registration house (where you can pay for parking for ...
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  • Phoenicia, New York

    Camp at Woodland Valley

    3.0
    If you are looking for a great campground up in the Catskill Mountains of New York then you definitely have to check out Woodland Valley Campgrounds. Located about 2 hours north of New York City, it is the perfect place to go to get off the grid. No service for about 30 minutes in any direction.T...
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  • Danbury, Connecticut

    Hike Middle Mountain To Thomas Mountain Loop

    3.7 mi / 856 ft gain
    Middle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
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  • Elka Park, New York

    Camp at Sugarloaf Mountain in the Catskills

    4.0
    6 mi / 1500 ft gain
    Begin by parking at the end of Mink Road in Elka Park (GPS:N42 08.593, W74 09.479). It will be a .7 mile hike to camp. Follow the rocky woods road to the junction where there is a SPRING sign. Continuing straight will take you to the water source. If you do not need water, turn left when you see ...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Big Indian, New York

    Camp on Giant Ledge

    4.5
    1.5 mi / 975 ft gain
    Giant Ledge is a great hike in the Catskills if you are looking for something short, with incredible views, and camping options. There are not many hikes with better views then this in the Catskills, so why not spend as much time as possible up there?  There are a few camping spots you can grab w...
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  • Big Indian, New York

    Hike Giant Ledge

    4.5
    3.74 mi
    The trail starts across the street from the parking area you will see a sign. After a short walk in you will cross a foot bridge. At approximately 0.75 mile you will reach a junction. You will turn left toward Giant Ledge. The next half mile is fairly flat. At 1.5 miles you will reach a spur ...
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  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
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