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Rutland, Massachusetts

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

Top Chillin Spots in and near Rutland

  • Clinton, Massachusetts

    Watch a Sunset at Wachusett Reservoir

    4.5
    Wachusett Reservoir is located in central Massachusetts, northeast of Worcester. Easy location and parking, you can go anytime of the day and you won't be disappointed. The Reservoir is the second largest body of water in the State of Massachusetts, taking place in 5 cities around the area, West ...
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  • Bolton, Massachusetts

    Take a Stroll at Fyfeshire Conservation Area

    1.0
    Fyfeshire is located in Bolton Massachusetts off "Wattaquadock Hill Road", near the "Fotini's Restaurant and Bar". The trailhead begins at a small parking area with a stone gate that says Fyfeshire Conservation area on a wood plank. Once you are in the conservation area you will see an opening in...
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  • Sutton, Massachusetts

    Hike the Purgatory Chasm Trail

    4.7
    1 mi / 115 ft gain
    For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.
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  • Groton, Massachusetts

    Catch a Sunset at Gilbert Hill

    5.0
    1 mi
    From Rt. I-495 Exit 31, Gibbert Hill has one of the greatest sunsets around Groton, MA area. You will see a lot of cows and even a castle. This is a very easy hike and a not so easy place to park, you have to leave you car on the side of the road, which is totally fine, I guess, it is easy.The wa...
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  • Acton, Massachusetts

    Hike the Pratt's Brook Conservation Area Loop

    4.0
    1.5 mi / 85 ft gain
    Park in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192.  The loop is very diverse wit...
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  • Chaplin, Connecticut

    Hike to Diana's Pool

    4.0
    1.3 mi / 45 ft gain
    The drive to Diana's Pool is worth it in an of itself, taking you through the backroads of Eastern Connecticut. To begin the hike just simply enter the woodland path and follow the trail. In order to go under the bridge just simply take the first left in the path and there will be a stream that f...
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  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...
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