Dog Friendly Hiking Trails in Sheffield, MA

There are 28 dog-friendly hiking trails within 20 miles of Sheffield. Use the links below to get an overview of each one, see pictures, print directions, and even read reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Sheffield.

Housatonic Meadows State Park

Sharon, CT

Housatonic Meadows State Park Leashed dogs are welcome at Housatonic Meadows State Park, a pet-friendly state park in Sharon, CT. This popular park is located in the rock-strewn valley of the Housatonic River and is a great place to get back to nature. Dogs are welcome on the hiking trails and in picnic areas, but are not permitted in the campground of the park. See Details

Paugnut State Forest

Torrington, CT

Paugnut State Forest Paugnut State Forest is a dog-friendly recreation area welcoming you and your leashed pup in Torrington, CT. The forest is spread over 1,700 acres across four different locations, including Burr Pond and Sunny Brook. The main section of Paugnut is home to the 2.1-mile John Muir Trail, a pet-friendly trail that connects two separate wooded areas. The forest recreation areas are open from sunrise to sunset. See Details

Sandisfield State Forest

Sandisfield, MA

Sandisfield State Forest Leashed pups are welcome at Sandisfield State Forest, a dog-friendly recreation area in Sandisfield, MA. Home to a northern hardwood forest that sprawls across the park, this popular space offers the 2.2-mile moderately challenging Pond Loop Trail for you and Fido to explore. Kayaking and fishing are also popular at the scenic York Lake. However, dogs are unfortunately not permitted on any of the beaches or landscaped lawns at this state forest. See Details

Housatonic State Forest

Cornwall, CT

Housatonic State Forest Leashed dogs are welcome to explore parts of the Housatonic State Forest in Cornwall, CT. This pet-friendly recreation area boasts a variety of amenities for parkgoers, including hiking, hunting, letterboxing, mountain biking, snowmobiling and more. See Details

Becket Land Trust

Becket, MA

Becket Land Trust Becket Land Trust is a pet-friendly recreational hub in Becket, MA. Your leashed furry companion can tag along to explore over 300 areas. Established by a dedicated group of citizens, the park aims to preserve the town's rustic charm, safeguard its natural resources and conserve ecologically sensitive zones. Please keep your pup under control during your visit, and be aware that a parking fee is applicable. See Details

East Mountain State Forest

Great Barrington, MA

East Mountain State Forest East Mountain State Forest is a pet-friendly route in Great Barrington, MA. Your leashed canine companion can tag along as you hop on this challenging trip along the Appalachian Trail. The area features four beautiful overlooks with views of three states. Please note the terrain is rugged and that the area is a habitat for coyotes, bears, deer, and turkeys. See Details

Taconic State Park

Copake Falls, NY

Taconic State Park Taconic State Park is a pet-friendly recreation area in Copake Falls, NY. You and your leashed dog can enjoy hiking the park's trails, camping, fishing, and picnicking. A maximum of two pets can join you at this park, and they must be supervised and on a six-foot or shorter leash throughout their visit. Pets aren’t permitted in buildings, playgrounds, golf courses, boardwalks, pools, spray grounds or guarded beaches. Please clean up after Fido. See Details

Monument Mountain Reservation

Great Barrington, MA

Monument Mountain Reservation Leashed dogs are allowed at Monument Mountain Reservation in Great Barrington, MA. This pet-friendly natural space features beautiful and moderately strenuous hiking trails. One trail reaches the 1,642-foot summit of the mountain and offers incredible Housatonic River Valley views. See Details