Dog Friendly Activities in Chester, MA

There are 28 dog friendly activities within 20 miles of Chester. 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 Chester.

Herman Melville’s Arrowhead

Pittsfield, MA

Herman Melville’s Arrowhead Leashed dogs are welcome on the grounds and inside the gift shop at the pet-friendly Herman Melville’s Arrowhead in Pittsfield, MA. Bring Fido and learn more about the famous author who penned "Moby-Dick." Take a stroll along Melville Trail to view the places that provided inspiration for his work. Please note dogs are not permitted inside the historic home. See Details

Mount Greylock State Reservation

Lanesborough, MA

Mount Greylock State Reservation Leashed dogs are welcome at Mount Greylock State Reservation, a pet-friendly park in Lanesborough, MA. You and Fido can explore the miles of hiking trails, rated from casual to strenuous. You can also drive the seasonally available summit road to the peak of the state's highest point. See Details

Stanley Park

Westfield, MA

Stanley Park Stanley Park in Westfield, MA is pet-friendly. Bring your leashed dog along for a walk on the paved trails, then relax on the grassy areas and look out for lesser-spotted black squirrels who call the park home. Pick up after your pup and place any waste in the trash cans provided. 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

Hampton Ponds State Park

Westfield, MA

Hampton Ponds State Park Leashed dogs are allowed at Hampton Ponds State Park, a pet-friendly natural space in Westfield, MA. This spot is perfect for exploring the shoreline with Fido, boating, kayaking, picnicking and fishing. See Details

Westfield Dog Bark

Westfield, MA

Westfield Dog Bark Fido can play and socialize off-leash at Westfield Dog Bark in Westfield, MA. This fenced dog park is a spacious area for pups that offers partial shade from tree cover, a water spigot (not available during winter months), wood chip ground cover, waste stations, benches and picnic tables. See Details

Berkshire Canoe Tours

Lenox, MA

Berkshire Canoe Tours Berkshire Canoe Tours hosts dog-friendly tours in Lenox, MA. Fido is welcome to join you as you canoe or kayak along the Housatonic River. Enjoy the beautiful scenery and wildlife as you paddle. Reservations are required. 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

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

Granville State Forest

Granville, MA

Granville State Forest Leashed pups are welcome at Granville State Forest, a remote, dog-friendly natural space in Granville, MA. You can bring Fido with you to hike on trails through the woods that lead to waterfalls through stunning forests. Once you're finished exploring the area with your furry best friend, you can rest your heads at one of the pet-friendly campsites deep in the woods. 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

Ashuwillticook Rail Trail

Cheshire, MA

Ashuwillticook Rail Trail The Ashuwillticook 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 Cheshire! The map below shows a parking area with convenient access to the Ashuwillticook 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

C.M. Gardner State Park

Huntington, MA

C.M. Gardner State Park Leashed dogs are welcome at C.M. Gardner State Park in Huntington, MA, where you and Fido can explore the Berkshire foothills along the Westfield River. The pet-friendly trails in this park will take you through varied woodland and you may even come across a variety of wildlife along the way. See Details

Kenneth Dubuque Memorial State Forest

Hawley, MA

Kenneth Dubuque Memorial State Forest Leashed pups can join you as you explore Kenneth Dubuque Memorial State Forest, a dog-friendly natural space in Plainfield and Hawley, MA. You and Fido can enjoy the 35 miles of mixed-use trail network that weaves through this 7,882-acre woodland park. 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

Windsor State Forest

Windsor, MA

Windsor State Forest Leashed dogs are welcome at Windsor State Forest, a pet-friendly natural space in Windsor, MA. Visitors are drawn to this pretty park for the views of the Berkshire Hills. You and Fido can explore the area together, including Windsor Jambs waterfall and the Windsor Jambs Brook that weaves through a wide gorge with 80-foot granite walls. See Details

Tunxis State Forest

Hartland, CT

Tunxis State Forest Tunxis State Forest is a pet-friendly recreation area in Hartland, CT, where leashed dogs and their owners can explore together. A variety of activities are available to parkgoers, including hiking, mountain biking, fishing, hunting and more. See Details

Chesterfield Gorge

Chesterfield, MA

Chesterfield Gorge Chesterfield Gorge is a pet-friendly recreational hub in Chesterfield, MA. Your furry friend can join you as you explore the area. Upon hiking the half-mile trail, you'll witness a dramatic rock canyon and the Westfield River, a popular spot for catch-and-release fly fishing. Please ensure Fido remains on a leash during your stay. See Details