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    Dog Friendly Hiking Trails in Great Barrington, MA

    There are 2 dog-friendly hiking trails in Great Barrington, and 21 more nearby. 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 Great Barrington.

    Pet Friendly East Mountain State Forest

    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
    Pet Friendly Monument Mountain Reservation

    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

    Bash Bish Falls State Park

    Mount Washington, MA
    Bash Bish Falls State Park Leashed dogs are welcome at Bash Bish Falls State Park in Mount Washington, MA. The centerpiece of the park, the stunning falls, are the highest single drop waterfalls in the state. You and Fido can view this natural wonder from the overlook or explore the area on the pet-friendly trails that weave around the park. See Details

    Norman Rockwell Museum

    Stockbridge, MA
    Norman Rockwell Museum Leashed dogs are welcome to join you as you explore the pet-friendly grounds of the Norman Rockwell Museum in Stockbridge, MA. The Museum houses the world’s largest and most significant collection of Rockwell’s work, and while Fido can not browse the artwork inside, the grounds offer 36-acres to explore that include sculptures, lovely landscaping, scenic views and picnic tables. See Details

    Pittsfield State Forest

    Pittsfield, MA
    Pittsfield State Forest Leashed dogs are welcome at Pittsfield State Forest, a pet-friendly natural area in Pittsfield, MA.There are 30 miles of trails to explore at this huge, 11,000-acre park, including the Taconic Crest Trail and the Tranquility. Berry Pond is also a popular spot in the park that offers swimming and fishing opportunities. See Details

    Harlem Valley Rail Trail

    Copake, NY
    Harlem Valley Rail Trail The Harlem Valley Rail Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Copake! The map below shows a parking area with convenient access to the Harlem Valley Rail Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    October Mountain State Forest

    Lee, MA
    October Mountain State Forest Leashed dogs are welcome at October Mountain State Forest, a pet-friendly park in Lee, MA. You and Fido can explore numerous different trails, including a portion of the Appalachian Trail and the Gorge Trail which passes the scenic Shermerhorn Gorge. Fishing, kayaking and cross-country skiing are also popular activities. See Details

    Beartown State Forest

    Monterey, MA
    Beartown State Forest Leashed dogs are allowed at Beartown State Forest in Monterey, MA. Home to a 12,000-acre forest and Benedict Pond, you and Fido can take on the pet-friendly Benedict Pond Loop Trail, which circles the scenic pond. Although a nice location year round, one of the best times to visit is in autumn to enjoy the breathtaking fall foliage. See Details

    Haystack Mountain State Park

    Torrington, CT
    Haystack Mountain State Park Haystack Mountain State Park is home to a rugged dog-friendly hike that winds all the way up to a 34-foot high stone tower at the summit of Haystack Mountain in Torrington, CT. If you don't fancy the hike, there's a road that leads to the top as well. Leashed pups are welcome in the picnic areas and on all of the hiking trails at this popular state park. See Details

    Wahconah Falls State Park

    Dalton, MA
    Wahconah Falls State Park Leashed pups can join you at Wahconah Falls State Park, a dog-friendly park in Dalton, MA. You and Fido can explore the half-mile loop trail along the upper falls that offers stunning views. This park also features fishing opportunities and scenic picnic areas. See Details

    Mount Washington State Forest

    Mount Washington, MA
    Mount Washington State Forest Leashed dogs are welcome at Mount Washington State Forest in Massachusetts. There are more than 30 miles of pet-friendly trails to explore with Fido. One of the most popular is the South Taconic Trail that leads to the summit of Alander Mountain and offers stunning views. See Details

    Dennis Hill State Park

    Norfolk, CT
    Dennis Hill State Park Dennis Hill State Park is a pet-friendly recreational area in Norfolk, CT. This 240-acre estate offers plenty of hiking opportunities and panoramic views from the summit overlook. Fido is welcome to join you in picnic areas and on hiking trails, but he must be leashed at all times. See Details

    Algonquin State Forest

    Winsted, CT
    Algonquin State Forest Fido is welcome to join you as you hike in the beautiful Algonquin State Forest, a pet-friendly area in Winsted, CT. Pets must be on a leash at all times. This park features hiking trails, wildlife viewing and more. See Details

    Railroad Ramble

    Lakeville, CT
    Railroad Ramble The Railroad Ramble is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Lakeville! The map below shows a parking area with convenient access to the Railroad Ramble. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Harlem Valley Rail Trail

    Millerton, NY
    Harlem Valley Rail Trail The Harlem Valley Rail Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Millerton! The map below shows a parking area with convenient access to the Harlem Valley Rail Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Campbell Falls State Park Reserve

    Norfolk, CT
    Campbell Falls State Park Reserve Campbell Falls State Park Reserve is a pet-friendly recreational area in Norfolk, CT. This natural area offers plenty of hiking experiences for you to enjoy with your dog. Just keep Fido on a leash at all times. See Details

    Mount Everett State Reservation

    Mount Washington, MA
    Mount Everett State Reservation Leashed dogs are allowed to join their humans at Mount Everett State Reservation in Mount Washington, MA. The centerpiece of this pet-friendly park is in the name, Mount Everett, which stretches 2,624-feet into the sky. You and Fido can wander the hiking trails that wind up to the peak, where, on a clear day, you'll discover 360 degree views of three states: Massachusetts, Connecticut, and New York. There are a number of other hiking trails that lead through the scenic woodland of this lovely park. See Details

    Jug End State Reservation and Wildlife Management Area

    Egremont, MA
    Jug End State Reservation and Wildlife Management Area Leashed dogs are welcome at Jug End State Reservation and Wildlife Management Area in Egremont, MA. This pet-friendly park is home to scenic views of the Berkshire Hills. In addition to having numerous hiking trails for you and Fido to explore, Jug End also offers access to the Appalachian Trail. 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

    High Falls Conservation Area

    Hudson, NY
    High Falls Conservation Area High Falls Conservation Area is a pet-friendly natural preserve in Hudson, NY. This natural wonder boasts beautiful waterfalls that are surrounded by trees. Four-legged friends are welcome to join you for a walk on one mile of winding trails. Dogs must be leashed and cleaned up after. See Details
    Great Barrington, MA, US