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  • Dover Plains, New York

    Top Spots in and near Dover Plains

    • Meriden, Connecticut

      Hike the Metacomet, Blue, and Yellow Loop

      5.0
      4.5 mi / 976 ft gain
      Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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    • Berlin, Connecticut

      Hike the Ragged Mountain Memorial Preserve

      4.5
      5.5 mi / 560 ft gain
      Ragged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds.  The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...
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    • Cragsmoor, New York

      Sam's Point, Ice Cave Trail, Verkeerderkill Falls

      4.9
      6.99 mi / 1063 ft gain
      Located in Sam's Point Preserve, this hike has three major attractions – panoramic views from Sam's Point, mysterious and chilly Ice Caves, and a knee-weakening perch atop Verkeerderkill Falls. Pay attention to seasonal conditions before making this trip. Spring and early summer are best for see...
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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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    • Cragsmoor, New York

      Sam's Point Overlook to Ice Cave Trail

      3.47 mi / 584 ft gain
      Sam's Point Overlook to Ice Cave Trail is an out-and-back trail with scenic views near Lake Maratanza located near Ellenville, New York. This trail is dog friendly on-leash. 
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    • 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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    • Simsbury, Connecticut

      Hike to the Heublein Tower on Talcott Mountain

      4.3
      2.54 mi / 404 ft gain
      The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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    • Hamden, Connecticut

      Mountain Bike West Rock Ridge State Park

      West Rock Ridge State Park is a 700 ft high scenic ridge that is located on the west side of New Haven. There are tons of good mountain biking trails located all around the ridge that can satisfy all types of skill levels. The easiest place to park is the Lake Wintergreen parking lot, which sits ...
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    • Hamden, Connecticut

      Hike the Tower Trail to the Blue Trail at Sleeping Giant SP

      5.0
      3 mi / 518 ft gain
      Sleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...
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    • Hamden, Connecticut

      Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP

      5.0
      3 mi / 518 ft gain
      Since I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...
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    • Hamden, Connecticut

      Boulder & Free Climb off the Blue Trail In Sleeping Giant SP

      Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...
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    • Briarcliff Manor, New York

      Hike Kate Kennard Trail

      1.8 mi / 140 ft gain
      If you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...
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    • Meriden, Connecticut

      Higby Mountain Trail

      2.11 mi / 486 ft gain
      The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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    • Bridgeport, Connecticut

      Stroll around Fayerweather Island

      0.5 mi
      Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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    • Grahamsville, New York

      Swim at Peekamoose Blue Hole

      3.8
      To get there: From Sundown, NY, head 10 miles on Route 42 until you see a large parking area on the right with a sign for the Peekamoose Mountain area. Follow the signs from the parking area to the creek. Swimming Hole Coordinates: (41.9182, -74.4215) You can cool off from NY's warm weather and d...
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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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