Other Dog Activities in Sheffield, MA

Take Fido to the dog-friendly tasting room at Sunset Meadow of Massachusetts Winery, located in Sheffield, MA. Fido is welcome inside the winery or beside you at an outdoor table and must remain leashed. Dogs who visit Sunset Meadow should be friendly towards people, other pets, and be well socialized. Try a wine flight and take home a souvenir glass, or sip a refreshing ice-cold wine slushie. Sunset Meadow produce a selection of the finest New England wine and also sell small-batch seasonal bottles along with local meats, cheeses, spreads and crackers.

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.

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.

Leashed dogs are welcome in outdoor spaces (weather permitting) at Land of Nod Vineyard & Winery, a pet-friendly winery in East Canaan, CT. Situated in the foothills of the Berkshires, on land steeped in early American History, this popular vineyard is a great place to hang out with your pup and sample a glass of fine wine. Open seasonally; check their website for current hours.

Forged Brewing Co. in Bainbridge, NY, is a charming brewery and winery nestled in the woods of Coventry. Enjoy a relaxing atmosphere, flavorful beers and tasty wines. Well-behaved, leashed dogs are welcome at the pet-friendly outdoor seating area.

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.

Beckley Furnace Industrial Monument is a pet-friendly site in East Canaan, CT. Part of the National Register of Historic Places, the Beckley Furnace was once the site of iron production for railroad car wheels. Now you and Fido can enjoy a guided experience of this site or take advantage of the interpretive signs and wander around on your own. Just keep Fido on a leash at all times.

Dogs are welcome at Mount Riga State Park in Salisbury, CT, home to the largest mountain in all of Connecticut, Bear Mountain. This pet-friendly park is popular among hikers and their dogs as it provides an easy access point the Appalachian Trail. From the stone pyramid at the top of the mountain, you can enjoy panoramic views of the valleys and peaks of New York, Massachussetts, and Connecticut in the surrounding area.

Platt Hill State Park is a pet-friendly recreation area that covers 159 acres in the town of Winsted, CT. They welcome pooches to join their owners on the trails around the area. Although the area is not maintained, you can still access some trails and have a look around the pretty area.

Bring Fido to the Four Brothers Drive In in Amenia, NY. Pets are welcome on the patio, in the drive in area and there is even a pet park for the pups to romp around in! Make sure to get your furry friend a house dog treat. Onsite, overnight camping and private event space is also available.