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  • Litchfield County, Connecticut

    Top Spots in and near Litchfield County

    • 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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    • 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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    • 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

      Backpack the Eastern Half of Devil's Path in the Catskill Mountains

      5.0
      14 mi / 3900 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

      Backpack Devil's Path in the Catskills

      24.2 mi / 9000 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 lif...
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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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    • 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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    • Haines Falls, New York

      Summit North Mountain

      4.5
      6 mi / 855 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.Parki...
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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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    • 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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    • Haines Falls, New York

      Kaaterskill Falls

      4.5
      2.57 mi / 719 ft gain
      Although this is a super short hike, it is definitely a tough one! The quick, steep climb is totally worth it once you reach the 260 foot cascade and pool at the end. Hike along the trail, hugging Spruce Creek all the way to the falls. If you hike in the spring, the creek and the falls will be ra...
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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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