Dog-Friendly Activities in Middlefield, MA

There are 32 dog-friendly activities within 40 kilometers of Middlefield. 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 Middlefield.

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

The Mount, Edith Wharton's Home

Lenox, MA

The Mount, Edith Wharton's Home The Mount, Edith Wharton's Home, is a dog-friendly venue in Lenox, MA. The famous novelist loved dogs, and as such, Fido is welcome to join you on the grounds as long as they remain leashed. Visit and see the home that Edith Wharton designed herself, right down to the sunken Italian garden. 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

Ashuwillticook Rail Trail

Adams, 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 Adams! 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

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

Pittsfield Dog Park

Pittsfield, MA

Pittsfield Dog Park Fido is sure to enjoy a day spent with friends at Pittsfield Dog Park, located in Pittsfield, MA. The dog park is a fully-fenced in, off leash area with separate spaces for large and small dogs. Well-behaved dogs are welcomed to exercise and socialize in a clean, safe environment. A hydration station will provide relief for thirsty pets at play! Dogs visiting Pittsfield Dog Park must be at least six months old and be licensed, vaccinated and spayed or neutered. All dogs should be wearing their tags and remain within view of their owners. The dog park is open from dawn until dusk. 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

Les Trois Emme Winery and Vineyard

New Marlborough, MA

Les Trois Emme Winery and Vineyard Fido can join you in outdoor spaces at Les Trois Emme Winery and Vineyard in New Marlborough, MA. This family-owned, dog-friendly winery offers wine tastings and lovely vineyard views. You and your leashed pup are welcome to explore the grounds. Please be sure to call the winery during inclement weather to confirm they are open prior to visiting. 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

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

Adams Dog Park

Adams, MA

Adams Dog Park Dogs can enjoy off-leash play at Adams Dog Park in Adams, MA. This fenced recreation area features double-gated entry, a picnic table, waste stations with disposal bags, and nearby parking for easy access. Fido should be leashed when entering and exiting the dog park area. See Details

Sena Farm Brewery

Worthington, MA

Sena Farm Brewery Sena Farm Brewery is a dog-friendly brewery nestled in the foothills of the Berkshires in Worthington, MA. Fido is welcome inside the barn and to explore the farm outside. Guests can enjoy a variety of style beers like pale ale, saison, IPA and pilsner. The brewery also hosts special events and food trucks. Check their website for a current schedule. 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

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

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

Tolland State Forest

Otis, MA

Tolland State Forest Tolland State Forest is a pet-friendly spot in Otis, MA. Your four-legged companion can tag along as you explore the area. Activities include hiking, sailing, fishing and kayaking. Please be aware of hunting season and note that there's a parking fee and dogs can't use the beach. See Details

Parsons Marsh Reserve

Lenox, MA

Parsons Marsh Reserve Parsons Marsh Trail in Lenox, MA, offers a scenic dog-friendly walk through the woods. This 0.6-mile round-trip trail features a mix of packed trail and elevated boardwalk, making it accessible and easy to navigate. Built in 2018 to U.S. Forest Service accessibility standards, it’s a great spot for a peaceful stroll, geocaching or a picnic with your 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

Savoy Mountain State Forest

Florida, MA

Savoy Mountain State Forest Leashed pups can join their humans at Savoy Mountain State Forest in Florida, MA. There are 50 miles of pet-friendly trails that weave around this stunning forest. Kayaking, fishing and cross-country skiing are also popular here. Autumn is an especially beautiful time of year to visit the park and marvel at the fall foliage. See Details