Dog-Friendly Activities in New Ashford, MA

Leashed pups are allowed to join you at Hilltop Orchards, a pet-friendly, family-run orchard, cidery and winery in Richmond, MA. Home to 16 acres of prime apple trees, you can enjoy apple cider, artisanal craft ciders, wine tastings and incredible apple cider donuts made fresh daily. Then, explore the hiking trails throughout the property that offer excellent Berkshire views.

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.

Fido is welcome to join you inside or at an outdoor table at Balderdash Cellars, a pet-friendly winery in Richmond, MA. Enjoy a variety of wine options including white, red and rosé, which you can buy by the glass or try multiple by doing a tasting. You are welcome to bring your own food.

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.

Leashed dogs are welcome to join their owners at Natural Bridge State Park in North Adams, MA. This pet-friendly park is home to the only natural white marble arch in North America, well worth a visit. At over 13,000 years old, the natural bridge is made of 550 million year-old bedrock marble that is carved into arches like a bridge. Please note that this seasonal park is open from late May through late October.

TurnPark Art Space in West Stockbridge, MA, invites leashed dogs to join you as you view a variety of contemporary architecture and sculptures. The former marble quarry features 16 acres of land with a diverse topography, including hills, meadows, and a lake. The park consists of two levels. The lower level is paved with marble chip and limestone and the upper level retains its natural appearance.

The Clark Art Institute invites leashed dogs to enjoy a walk on the outside grounds and network of trails at this renowned museum in Williamstown, MA. Surrounded by 140 acres of grassy lawn, meadows and walking trails, this pet-friendly destination offers plenty of green spaces for you and Fido to explore together.

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.

Bennington Battle Monument is pet-friendly. Standing over 306ft tall, the monument was completed and dedicated in 1891 and constructed from blue-grey magnesian limestone. Commemorating the Battle of Bennington in the Revolutionary War, the trails and grounds surrounding the monument welcome leashed dogs to explore with their owners. The Monument is open Friday through Monday from 10am to 5pm.

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.

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.

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.

Enjoy fresh air and exercise with Fido at the dog-friendly Uno Park in North Adams, MA. This public park, owned and maintained by the Massachusetts Museum of Contemporary Art, is a recreation area featuring picnic seating, a bocce ball area, pickleball court and a basketball half-court. Fido must remain on a leash while visiting the park.

Bennington Dog Park is a fenced space located in Willow Park in Bennington, VT. After an on-leash trip to Bennington Battle Monument, one of the region’s most popular attractions, you can let your dog off-leash at this cool fenced space. The dog park is a shady half-acre spot, perfect for running wild on sunny days and meeting other pups. Bennington Dog Park is open every day of the week from dawn until dusk.

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.

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.

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.

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.

Leashed dogs are allowed at Clarksburg State Park in Clarksburg, MA. This pet-friendly park is especially popular during the fall months, when the trees offer stunning colors as the leaves change. There are a number of trails for you and Fido to explore, some that even follow along a scenic lakeshore.

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.