Glastonbury, Connecticut
Looking for the best hiking in Glastonbury? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Glastonbury. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Glastonbury
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North Stonington, Connecticut
Hike Wyassup Lake
5.02.4 mi / 278 ft gainWyassup Lake is a 2.4 mile out and back hike that takes you past great forest setting located near North Stonington, Connecticut.Read more -
Sharon, Connecticut
Hike the Pine Knob Loop, Housatonic Meadows SP
5.02.5 mi / 770 ft gainThe Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...Read more -
Stonington, Connecticut
Hike Denison Pequotsepos Nature Center Trail
5.01.7 mi / 72 ft gainDenison Pequotsepos Nature Center Trail is a 1.7 mile loop hike that takes you by a river located near Mystic, Connecticut.Read more -
Kent, Connecticut
Explore Kent Falls
5.00.75 mi / 250 ft gainEvery 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...Read more -
Canaan, Connecticut
Explore Great Falls
3.00.5 miStumbled 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.Read more -
West Greenwich, Rhode Island
Stepstone Falls via Ben Utter Trail
5.02.64 mi / 125 ft gainStepstone Falls via Ben Utter Trail is an out-and-back trail that takes you by a waterfall located near West Greenwich, Rhode Island.Read more -
Hopkinton, Rhode Island
Hike to Long Pond & Ell Pond
5.05.7 miLong & 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...Read more -
Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For 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 -
New Fairfield, Connecticut
Hike Squantz Pond Trail
2.2 mi / 321 ft gainThe hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...Read more -
Salisbury, Connecticut
Bear Mountain Loop
4.56.05 mi / 1516 ft gainAt 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...Read more -
Shelter Island, New York
Hike through the Mashomack Nature Preserve
10 miJust a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...Read more -
Westerly, Rhode Island
Napatree Point Conservation Area Trail
4.03.19 mi / 82 ft gainNapatree Point Conservation Area Trail is a loop trail that takes you past scenic surroundings located near Westerly, Rhode Island.Read more -
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...Read more -
Douglas, Massachusetts
Hike the Coffeehouse Loop, Douglas State Forest
3.02.2 mi / 500 ft gainDouglas 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 ...Read more -
Sheffield, Massachusetts
Hike to Race Brook Falls
4.03.4 mi / 1174 ft gainHiking 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 ...Read more -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more