Other Dog Activities in Monterey, 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.

See Details

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

Balderdash Cellars

Richmond, MA

Balderdash Cellars

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.

See Details

Land of Nod Vineyard & Winery

East Canaan, CT

Land of Nod Vineyard & Winery

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.

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

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

TurnPark Art Space

West Stockbridge, MA

TurnPark Art Space

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.

See Details

Mount Riga State Park

Salisbury, CT

Mount Riga State Park

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.

See Details

Platt Hill State Park

Winsted, CT

Platt Hill State Park

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.

See Details

Beckley Furnace Industrial Monument

East Canaan, CT

Beckley Furnace Industrial Monument

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.

See Details

Pleasant Valley Drive-In

Barkhamsted, CT

Pleasant Valley Drive-In

Pleasant Valley Drive-In is a pet-friendly drive-in movie theater in Barkhamsted, CT. This nostalgic pastime is still going strong and invites you to bring your pooch along to watch a new release or a classic feature from the comfort of your car. Dog owners are reminded not to disturb other moviegoers by only bringing well-behaved dogs along who won't bark at the exciting scenes. If your dog needs a bathroom break, don't forget to clean up any mess that is left behind. Please note that Pleasant Valley Drive-In is cash only and open seasonally. Check their website for opening dates.

See Details

Sunset Meadow of Massachusetts

Sheffield, MA

Sunset Meadow of Massachusetts

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.

See Details

Big Elm Brewing - Great Barrington Taproom

Great Barrington, MA

Big Elm Brewing - Great Barrington Taproom

Locally, women-owned Big Elm Brewing in Great Barrington, MA is pet friendly. Bring Fido along while you enjoy house-brewed beers in a variety of styles, and be sure to request a milk bone from the bar staff! Dogs are allowed inside taproom and outside on the porch., and while they don't serve food on site, you're welcome to bring in or order food from nearby establishments.

See Details