Middletown, Connecticut
Looking for the best hiking in Middletown? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Middletown. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Middletown
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Mansfield, Connecticut
Hike Nipmuck Trail
5.08.3 mi / 748 ft gainNipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.Read more -
Norwich, Connecticut
Explore Yantic Falls Historic District
0.3 mi / 26 ft gainThe 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...Read more -
Granby, Connecticut
Hiking Enders Falls
4.0Enders 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 -
Chaplin, Connecticut
Hike to Diana's Pool
4.01.3 mi / 45 ft gainThe 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...Read more -
Washington, Connecticut
Hike the Mount Tom Tower Trail
1.3 mi / 337 ft gainStarting 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 -
Groton, Connecticut
Hike Sheep Farm
3.01 mi / 91 ft gainSheep Farm is a 1 mile loop hike that takes you by a waterfall located near Groton, Connecticut.Read more -
Groton, Connecticut
Hike Bluff Point State Park Eastern Loop
4.54.3 mi / 344 ft gainBluff Point State Park Eastern Loop is a 4.3 mile loop hike where you may see beautiful wild flowers located near Groton, Connecticut.Read more -
Washington, Connecticut
Hike Meeker Trail
3.3 mi / 639 ft gainMeeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.Read more -
Hampden, Massachusetts
Goat Rock Trail
2.67 mi / 659 ft gainGoat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.Read more -
Groton, Connecticut
Hike Haley Farm Loop
5.02.7 mi / 193 ft gainHaley Farm Loop is a 2.7 mile loop hike that takes you past wildlife located near Groton, Connecticut.Read more -
North Stonington, Connecticut
Hike Narragansett Trail
4.010.7 mi / 1 ft gainNarragansett Trail is a 10.7 mile point-to-point hike that takes you by a lake located near North Stonington, Connecticut.Read more -
Stonington, Connecticut
Hike River Road
4.03.9 mi / 55 ft gainRiver Road is a 3.9 mile point-to-point hike that takes you by a river located near Mystic, Connecticut.Read more -
Plainfield, Connecticut
Hike Sugar Brook Loop Trail
4.03.3 mi / 200 ft gainSugar Brook Loop Trail is a 3.3 mile loop hike that takes you by a river located near Plainfield, Connecticut.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 -
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 -
Voluntown, Connecticut
Hike Pachaug State Forest Trails
5.03.6 mi / 200 ft gainLawden Brook Trail Loop is a 3.6 mile loop hike that takes you by a lake located near Voluntown, Connecticut.Read more