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    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.

    Pet Friendly Bash Bish Falls State Park

    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
    Pet Friendly Norman Rockwell Museum

    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

    Burr Pond State Park

    Torrington, CT
    Burr Pond State Park Enjoy some exercise and a picnic with your pup at dog-friendly Burr Pond State Park in Torrington, CT. Explore the hiking trails with Fido in search of the bronze tablet marking Connecticut's role in the Civil War and the Industrial Revolution. Please note that pets are not permitted on the beach and must be leashed at all times during your visit. 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

    Sunnybrook State Park

    Torrington, CT
    Sunnybrook State Park Part of Paugnut State Forest and connected to it by the 2.1-mile John Muir Trail, Sunnybrook State Park is set on 464 wooded acres. This pet-friendly park in Torrington, CT offers plenty of trails, including five nature trails, and a pond to play and cool off in. Pack a lunch, wear comfortable shoes, and enjoy a memorable excursion with your leashed pup. 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

    Mohawk State Forest

    Goshen, CT
    Mohawk State Forest Mohawk State Forest is a dog-friendly recreational area in Goshen, CT. This area encompasses the towering Mohawk Mountain State Park and is a popular place for pets and their owners to explore together. The hiking trails and the picnic areas are both accessible to dogs. You may not be able to access the park during certain winter months, but it's worth calling ahead if you are unsure whether the park will be open when you intend on visiting. 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

    John A. Minetto State Park

    Torrington, CT
    John A. Minetto State Park Dogs are welcome at John A. Minetto State Park in Torrington, CT. This rolling, open land was previously known as Hall Meadow and contains a picturesque pond and a few pet-friendly trails for you and your leashed pup to enjoy. The park is open every day of the week from 8am until sunset. See Details

    Tolland State Forest

    Otis, MA
    Tolland State Forest Leashed dogs are welcome to join their owners at Tolland State Forest in East Otis, Massachusetts. The centerpiece of this pet-friendly park is Otis Reservoir, where you can enjoy fishing and boating. You and Fido can also explore the lovely trails here by hiking, biking or cross-country skiing. 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

    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

    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

    Harlem Valley Rail Trail

    Amenia, 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 Amenia! 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

    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
    Sheffield, MA, US