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  • Dover Plains
  • Dover Plains, New York

    Top Spots in and near Dover Plains

    • 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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    • Stockbridge, Massachusetts

      Laura's Tower and Ice Glen

      5.0
      2.4 mi / 676 ft gain
      You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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    • Southington, Connecticut

      Rock Climb Ragged Mountain

      The main face of Ragged Mountain (elev. 761 feet) is home to a lot climbing in central Connecticut. It runs north-south for about 600 feet. Its max height of 100 feet. The crag is home to several rock climbing guides and schools. Routes range in difficultly from great for the beginner (5.3) to su...
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    • Palenville, New York

      Kaaterskill Falls via Laurel House

      4.5
      1.67 mi / 360.89 ft gain
      This short hike is one of the most popular in the Catskills — and for good reason. From the Laurel House Road Trailhead, it’s less than a mile round trip to reach Kaaterskill Falls, New York’s tallest two-tiered waterfall, with a dramatic 260-foot drop into a rocky amphitheater. The trail itse...
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    • Elka Park, New York

      Layman's Monument and Kaaterskill Falls

      3.05 mi / 892 ft gain
      Layman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.
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    • Tannersville, New York

      North Mountain

      4.7
      6.16 mi / 1060 ft gain
      Have you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills. Par...
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    • 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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    • Tannersville, New York

      Kaaterskill Rail Trail + Kaaterskill Falls

      5.0
      3.61 mi / 246 ft gain
      The Kaaterskill Rail Trail begins near Haines Falls, New York heading toward North and South Lake. The trail is set in a gorgeous forest, and is used for hiking, trail running, and birding trips. The trail provides exceptional views of the surrounding mountains, valleys, forests, and towns. 
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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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