Plainfield, Connecticut
Looking for the best hiking in Plainfield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Plainfield. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Plainfield
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New Shoreham, Rhode Island
Explore Block Island
5.0Block Island, a small island off the coast of the Rhode Island mainland, is well-known as a local summer playland. Tourists typically go to the quaint New England island in the summer months for the biking, hiking, sailing, kayaking, fishing and 17 miles of beaches.Although you can bring a car o...Read more -
Middletown, Connecticut
Explore Wadsworth Falls
5.00.25 miWhen it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...Read more -
Montauk, New York
Stroll along the Montauk Point Lighthouse Cliff Walk
4.51 miThe Montauk Point Lighthouse is one of the main attractions of "The End" of Long Island, but I've only ever walked around it on the cliff walk.When you get to the lighthouse, you can park in the parking lot (depending on when you go there may be a $8 fee). Right along the edge overlooking the wa...Read more -
Meriden, Connecticut
Higby Mountain Trail
2.11 mi / 486 ft gainThe popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice! The beginning of the hike is mostly flatter land and an incline w...Read more -
Montauk, New York
Climb the Bluffs of Shadmoor State Park
1.2 mi / 100 ft gainI've never actually been into the Shadmoor State Park, but you can climb up and onto the bluffs from the beach easily; well kind of easily.Most of the parking lots along the beach require Hamptons residency tags, so you can't park right next to beach entrances... bummer. We typically park along ...Read more -
Ashland, Massachusetts
Hike the Ashland Reservoir Trail
5.03.2 mi / 68 ft gainPark in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked.Read more -
Berlin, Connecticut
Hike the Ragged Mountain Memorial Preserve
4.55.5 mi / 560 ft gainRagged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds. The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...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 -
Westport, Massachusetts
Hike Gooseberry Island
1.5 mi / 36 ft gainBegin an hour before sunset at the intersection between West Beach and East Beach Road. The intersecting roads will lead you to a paved causeway over the ocean. Waves typically clash on either side of you as you drive over the ocean. There is a free parking lot once you reach the opening. To reac...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 -
Southington, Connecticut
Hike the Crescent Lake & Metacomet Trail Loop
4.02.4 mi / 269 ft gainThe hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...Read more -
Meriden, Connecticut
Hike the Metacomet, Blue, and Yellow Loop
5.04.5 mi / 976 ft gainStart from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...Read more -
Dartmouth, Massachusetts
Hike Frank Knowles–Little River Reserve Trail
4.64 mi / 295 ft gainFrank Knowles-Little River Reserve contains nearly 9 miles of hiking trails to explore. Start off by parking in the white sea shell parking lot. From there you will find the trail marked by a DNRT sign . My group and I walked along the red/boardwalk trail which features a number of boardwalks lea...Read more