Middlesex County, Connecticut
Looking for the best hiking in Middlesex County? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Middlesex County. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Middlesex County
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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 -
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 -
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 -
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 -
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 -
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 -
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 -
Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe 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 ...Read more -
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 -
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 -
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 -
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 -
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 -
Westerly, Rhode Island
Grills Preserve
4.04.27 mi / 351 ft gainGrills Preserve is a loop trail that takes you by a lake located near Bradford, Rhode Island.Read more