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Sheffield, Massachusetts

Looking for the best chillin in Sheffield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Sheffield. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Sheffield

  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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  • Mount Washington, Massachusetts

    Climb Alander Mountain

    10.6 mi / 2250 ft gain
    Close to the popular Bash Bish Falls in Mount Washington State Forest is this amazing summit and perfect day hike! Witness the corners of Massachusetts, Connecticut, and New York all at once (and from the top of this trail, it connects to Bash Bish if you have the time to spear!) From the Mt. Was...
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  • Mount Washington, Massachusetts

    Explore Bash Bish Falls

    4.3
    1 mi
    One of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...
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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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  • 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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  • 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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  • Norfolk, Connecticut

    Hike to Campbell Falls

    4.0
    1.4 mi / 187 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
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  • Canaan, Connecticut

    Explore Great Falls

    3.0
    0.5 mi
    Stumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.
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  • Kent, Connecticut

    Explore Kent Falls

    5.0
    0.75 mi / 250 ft gain
    Every now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...
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  • Granby, Connecticut

    Hiking Enders Falls

    4.3
    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...
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  • 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...
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  • 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...
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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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  • Haines Falls, New York

    Camp at North Lake Campground

    During an unplanned road trip, we arrived at the North/South Lake Campground out of curiosity and without a doubt, it was totally worth the stop! (We only saw North Lake.) To visit this campground, there is a fee for a day pass, unless you had just came from another campground in the Catskills li...
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  • Haines Falls, New York

    Hike to the Old Catskill Mountain House Site

    0.5 mi / 750 ft gain
    Once upon a time, this very spot was home to one of the most glamorous hotel for travelers in the United States. Now it's a historical site with one hell of a view of the Hudson River, the far away hills of Vermont, Connecticut, Massachusetts, and of course the beautiful Catskills valleys. If you...
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