Outbound Collective logo
  • United States
  • Massachusetts
  • Great Barrington
  • Great Barrington, Massachusetts

    Top Spots in and near Great Barrington

    • Granby, Connecticut

      Hiking Enders Falls

      4.0
      Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...
      Read more
    • Kent, Connecticut

      Hike the Ridge Loop Trail, Macedonia Brook SP

      3.0
      For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...
      Read more
    • Adams, Massachusetts

      Explore Bellevue Falls

      5.0
      When you reach the falls, you can cliff jump into a large swimming hole at the base. The best time to visit the falls is from April to November. Please note that dogs are not permitted here. Parking is at a cemetery, and the gates are open from 8am to 9pm. Use common sense before cliff jumping - ...
      Read more
    • Williamstown, Massachusetts

      Hike the March Cataract Falls Trail

      4.0
      2.2 mi / 511 ft gain
      Park at the Junction of Sperry Rd and Rockwell Rd. To get to the trailhead, hike along Sperry Road for about 30 minutes. (Not to the end of the road, see map below.) Then hike along the March Cataract Trail, an out-and-back. You can bring dogs on leash. The trail is short but steep in some parts ...
      Read more
    • Williamstown, Massachusetts

      Hike Mt. Greylock via Money Brook Trail

      9.7 mi / 3034 ft gain
      Park in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...
      Read more
    • Dover Plains, New York

      Hike Dover's Stone Church

      4.5
      Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
      Read more
    • Savoy, Massachusetts

      Tannery Falls Loop

      0.54 mi / 135 ft gain
      The hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...
      Read more
    • Greene County, United States

      Hike to Newman's Ledge

      4 mi / 584 ft gain
      Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
      Read more
    • Washington, Connecticut

      Hike the Mount Tom Tower Trail

      1.3 mi / 337 ft gain
      Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
      Read more
    • Washington, Connecticut

      Hike Meeker Trail

      3.3 mi / 639 ft gain
      Meeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.
      Read more
    • Haines Falls, New York

      Fawns Leap

      2.3
      Please be respectful if visiting this local swimming hole. Pack out what you pack in, carry out others' trash, and familiarize yourself with Leave No Trace principles.  Hidden in the Catskill Mountains is one of the coolest cliff jumping locations I have ever been to. The first time I went was a...
      Read more
    • 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...
      Read more
    • 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.
      Read more
    • 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...
      Read more
    • 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 ...
      Read more
    • 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...
      Read more