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  • Dover Plains, New York

    Top Spots in and near Dover Plains

    • Gardiner, New York

      Hike The Millbrook Mountain Ridge Trail

      5.0
      7 mi / 1400 ft gain
      Want to walk on the edge? visit Millbrook Mountain in the Catskills of NY. This loops hike follows the mountains ridge line most of the way to the summit with multiple viewpoints and cliff ledges to walk out on. This hike is recommended those in the area.Park at West Trapps Parking Lot and head ...
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    • Gardiner, New York

      Hike the Overcliff - Undercliff Road Loop

      5.3 mi / 350 ft gain
      From the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk.  The trail connects the parking lot to the Overcliff Road/Undercliff Road junction.  The loop can be done in either direction.  I turned left on the Overcliff Road.  This takes you behind...
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    • Beacon Falls, Connecticut

      Hike the Spruce Brook Ravine

      4.0
      1 mi
      Working my way to the West side of the state, a friend recently helped me discover Naugatuck State Park in Naugatuck, CT. After driving up and around curvy roads, we entered the forest (with a lot of potholes). Here is a map of the park. The parking I am talking about here is the "P" symbol next ...
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    • Gardiner, New York

      Gertrude's Nose

      4.9
      6.97 mi / 919 ft gain
      It would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...
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    • Gardiner, New York

      Lake Minnewaska Loop Trail

      2.01 mi / 348 ft gain
      Lake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.
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    • Gardiner, New York

      Hike the Millbrook Mountain/Gertrude Nose loop

      9 mi / 1700 ft gain
      This great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...
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    • Pound Ridge, New York

      Leatherman's Loop

      1.25 mi / 1183 ft gain
      This loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...
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    • Philipstown, New York

      Hike the Osborn Loop

      7.6 mi / 850 ft gain
      The Osborn Loop trail itself is not a loop.  It connects to a 2.5 mile section of the Appalachian Trail.  Hiking these together creates the loop.  Start at the trail head for the Appalachian Trail on South Mountain Pass Road.  There is parking for two or three cars.  Walk up the road a short dist...
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    • New Windsor, New York

      Hike Jessup/West Ridge Loop via the Sweet Clover Trail

      10 mi / 1700 ft gain
      Schunnemunk Mountain State Park is one of my favorite parks.  It offers many trails and possibilities for different loops.  The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions.This hike starts at the Taylor Road parki...
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    • Great Barrington, Massachusetts

      Hike the Benedict Pond Loop Trail

      5.0
      1.7 mi
      This is no ordinary loop, it's rain forest-like feels with small hills and curves, wooden bridges over marsh, and lookouts over the pond will keep you in awe at every corner! The trail is easy to find and easy to follow. When you park at the boat launch area, follow the blue blazes and trail sign...
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    • Hudson, New York

      High Falls Conservation Area Loop

      1.41 mi / 194 ft gain
      High Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.
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    • Great Barrington, Massachusetts

      Mt. Wilcox and Beartown Mountain Trail Loop

      9.29 mi / 981 ft gain
      Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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    • Great Barrington, Massachusetts

      Camp at Beartown State Forest

      On a spontaneous adventure, we were lucky to have ended up car camping at the beautiful Beartown State Forest. From the main entrance of the state forest, the campsite is only a few minutes drive to the right of the road. The campsite is popular, but only limited to 12 sites, so during the summer...
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    • Philipstown, New York

      Anthony's Nose via Appalachian Trail

      4.6
      1.95 mi / 682 ft gain
      Parking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...
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    • Great Barrington, Massachusetts

      Hike the Lookout Trail in Beartown State Forest

      0.5 mi / 117 ft gain
      If you ever decide to go to the beautiful Beartown State Forest, be sure to enjoy the short but worthy hike to the vista on the Lookout Trail for views that stretches out to the mountains. There are two places to park:  1. From the main entrance of the park, you can get a spot at the lot at Bened...
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    • Cortlandt, New York

      Hike the Camp Smith Trail

      4.5
      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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