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Woodstock, Connecticut

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

Top Hiking Spots in and near Woodstock

  • Douglas, Massachusetts

    Hike the Coffeehouse Loop, Douglas State Forest

    3.0
    2.2 mi / 500 ft gain
    Douglas State Forest is located off of Rte 16 in south central Massachusetts. To access trails and the lake, head to the parking area on Wallum Lake Park Road. From the parking lot, you can access the Coffeehouse Loop Trail, as well as a few other shorter trails by the lake. The Coffeehouse Loop ...
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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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  • Plainfield, Connecticut

    Hike Sugar Brook Loop Trail

    4.0
    3.3 mi / 200 ft gain
    Sugar Brook Loop Trail is a 3.3 mile loop hike that takes you by a river located near Plainfield, Connecticut.
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  • Mansfield, Connecticut

    Hike Nipmuck Trail

    5.0
    8.3 mi / 748 ft gain
    Nipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.
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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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  • North Smithfield, Rhode Island

    Hike the Fort Wildlife Refuge

    1 mi
    The parking area is about 50 yards down the dirt driveway on your right. Take care in the spring, as the parking lot can become a mud pit!  This wildlife refuge is a series of loops which lead to three different ponds. These directions are for the 'Pond One' loop. When you start on the trail, sta...
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  • Blackstone, Massachusetts

    Hike the Blackstone Gorge Trail

    5.0
    0.7 mi / 72 ft gain
    Park at the lot at the corner of Staples Lane and County Street. From here you can access the Blackstone Gorge Trail. Dogs are allowed on leash, and you can enjoy various paths along the river or through the forest. At multiple points you can find yourself looking down at the Blackstone River fro...
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  • Franklin, Connecticut

    Hike Baileys Ravine at Ayer's Gap Preserve

    1.6 mi / 314 ft gain
    It's steep and rocky in the beginning but it levels out after a while! When standing in the parking lot, the trailhead is hidden! Look to the right. The trail ends on Ayer's Road so you have to walk back a little ways on the road.
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  • Voluntown, Connecticut

    Hike Pachaug State Forest Trails

    5.0
    3.6 mi / 200 ft gain
    Lawden Brook Trail Loop is a 3.6 mile loop hike that takes you by a lake located near Voluntown, Connecticut.
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  • Hampden, Massachusetts

    Goat Rock Trail

    2.67 mi / 659 ft gain
    Goat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.
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  • West Greenwich, Rhode Island

    Stepstone Falls via Ben Utter Trail

    5.0
    2.64 mi / 125 ft gain
    Stepstone Falls via Ben Utter Trail is an out-and-back trail that takes you by a waterfall located near West Greenwich, Rhode Island.
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  • Providence, Rhode Island

    Hike The Neutaconkanut Trails

    5.0
    To enter the park, you first have to go through a field and past a baseball park. Next, you will see a high slope, you can either enter the trails through here or the stairs at the side. Some of the trails are overgrown and may have ticks or poison ivy so be careful. This place is good for kids a...
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  • Norwich, Connecticut

    Explore Yantic Falls Historic District

    0.3 mi / 26 ft gain
    The Yantic Falls Historic District encompasses a historic mill and associated worker housing on Yantic Street in Norwich, Connecticut. The 10 acre area includes a complex of mill buildings arrayed along the Yantic River, and a group of three brick mill worker houses. Today, Yantic Falls is part d...
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  • Glastonbury, Connecticut

    Blackledge Falls

    4.0
    1.46 mi / 207 ft gain
    Although the park contains hiking trails, a pond and a streambelt, the primary draw of this parcel of land is the 25 foot waterfall. The falls flow varies depending on the volume of precipitation, from a trickle in the dry months to a three-pronged vertical drop after some consistent snow melt or...
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  • Hopkinton, Rhode Island

    Hike to Long Pond & Ell Pond

    5.0
    5.7 mi
    Long & Ell Pond is a favorite hike at any time of the year, but it is not for the faint of heart (or small children)! The path immediately becomes more of a rock-scrambling adventure than a hike, but the views are so worth it.  This GPS address will lead you down a dirt road but you should ea...
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  • North Stonington, Connecticut

    Hike Wyassup Lake

    5.0
    2.4 mi / 278 ft gain
    Wyassup Lake is a 2.4 mile out and back hike that takes you past great forest setting located near North Stonington, Connecticut.
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