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  • Poughkeepsie
  • Poughkeepsie, New York

    Top Spots in and near Poughkeepsie

    • Monroe, New York

      Hike the Jessup/Highlands/Long Path Trails

      7.8 mi / 500 ft gain
      This trails starts at a small park in Woodbury called Gonzaga Park.  Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking.  Three different trail names share this path.  The Jessup trail starts/end at Gonzaga Park and trave...
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    • Cortlandt, New York

      Camp Smith Trail

      4.0
      5.92 mi / 1759 ft gain
      This approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...
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    • Woodstock, New York

      Overlook Mountain Trail

      4.53 mi / 1348 ft gain
      It is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...
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    • Sharon, Connecticut

      Hike the Pine Knob Loop, Housatonic Meadows SP

      5.0
      2.5 mi / 770 ft gain
      The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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    • Grahamsville, New York

      Peekamoose Blue Hole

      4.6
      NOTE: There is a new permit system in place: Under the new no-cost permit system, visitors to the Blue Hole are required to obtain a permit on weekends and holidays from May 15 through October 15 every year. DEC will issue up to 40 permits per day and each permit allows entry for up to six indivi...
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    • Washington, Connecticut

      Hike Meeker Trail

      3.3 mi / 639 ft gain
      Meeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.
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    • Woodstock, New York

      Sugarloaf Mountain via Blue Trail

      6.54 mi / 2297 ft gain
      Sugarloaf Mountain, is one the 35 highest peaks in New York's Catskills at 3806 ft. There are many ways to approach this peak, and this is an out-and-back hike via Mink Hollow. The parking area is located at the end of Milk Hollow Rd (42.10405386879072, -74.17148500019927). From here, get on the...
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    • 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

      Kaaterskill High Peak Trail

      7.85 mi / 1982 ft gain
      There are no direct views from the summit, so it is recommended to take the .25 mile shoot-off trail to Hurricane Ledge for beautiful views of the surrounding mountains and valleys. In the spring, wildflowers line the trail. If you look carefully in the brush, you'll find wreckage from two old pl...
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    • Elka Park, New York

      Devil's Path to Devil's Tombstone

      5.0
      11.9 mi / 4475 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

      Devil's Path in the Catskills

      4.0
      22.04 mi / 7733 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 l...
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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

      5.0
      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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