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  • Great Barrington, Massachusetts

    Top Spots in and near Great Barrington

    • North Adams, Massachusetts

      The Cascades Trail

      4.3
      1.97 mi / 315 ft gain
      The Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.
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    • Litchfield, Connecticut

      Photograph Daffodils at Laurel Ridge

      Laurel Ridge is a private owned Farm , the owners are generous enough to let people visit these flowers so please be respectful of there rules.  You may see the Daffodils from Sunrise-Sunset and usually fully bloomed Early April-May. Laurel Ridge is the perfect way to start Spring, the smell and ...
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    • Elka Park, New York

      Hike to Huckleberry Point

      4.5
      4.5 mi / 644 ft gain
      This is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...
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    • Elka Park, New York

      Kaaterskill High Peak Trail

      7.85 mi / 1982 ft gain
      There are no direct views from the summit, so it is recommended to take the .25 mile shoot-off trail to Hurricane Ledge for beautiful views of the surrounding mountains and valleys. In the spring, wildflowers line the trail. If you look carefully in the brush, you'll find wreckage from two old pl...
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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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    • Elka Park, New York

      Hike to Plattekill Falls

      0.5 mi / 137 ft gain
      Just outside of Elka Park, New York, Plattekill Falls is accessible from Albany and New York City alike. This is a great hike for families and all skill levels. The falls are spectacular year-round, but the best time to visit is in the spring.  From the trailhead, walk left past the red house unt...
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    • Holyoke, Massachusetts

      Whiting Street Reservoir Loop

      3.74 mi / 138 ft gain
      Whiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.
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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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    • 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

      Devil's Path to Devil's Tombstone

      5.0
      11.9 mi / 4475 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

      Devil's Path in the Catskills

      4.0
      22.04 mi / 7733 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 l...
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    • Woodstock, New York

      Overlook Mountain Trail

      4.53 mi / 1348 ft gain
      It is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...
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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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    • Cropseyville, New York

      Hike Dickinson Hill Fire Tower

      4.5
      3 mi / 200 ft gain
      Once you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...
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    • 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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