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  • Dover Plains
  • Dover Plains, New York

    Top Spots in and near Dover Plains

    • Gardiner, New York

      Hike the Dickie Barre, Peters Kill and Awosting Falls Loop

      3.0
      7.8 mi
      This loop hike takes you to Awosting Falls (65 ft.), as well as to great  valley views along the ridge of Dickie Barre, and across Peters Kill, on the way.Start out on West Trapps Connector Trail (yellow blazes) at the east end of the West Trapps parking lot (get their early because the lot will ...
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    • 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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    • 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

      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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    • 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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    • 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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    • 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

      5.0
      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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    • 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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    • 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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    • Highland Falls, New York

      Popolopen Torne

      4.5
      1.18 mi / 531 ft gain
      Popolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...
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    • Bear Mountain, New York

      Hike Bald Mountain, Bear Mountain State Park

      4.7
      6.8 mi / 1080 ft gain
      From your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...
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    • Great Barrington, Massachusetts

      Hike Monument Mountain

      4.0
      2 mi / 720 ft gain
      At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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