Dog-Friendly Activities in Otis, MA

There are 2 dog-friendly activities in Otis, and 47 more nearby. 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 Otis.

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

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

Hilltop Orchards

Richmond, MA

Hilltop Orchards 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

Norman Rockwell Museum

Stockbridge, MA

Norman Rockwell Museum Leashed dogs are welcome to join you as you explore the pet-friendly grounds of the Norman Rockwell Museum in Stockbridge, MA. The museum houses the world’s largest and most significant collection of Rockwell’s work. While Fido can not browse the artwork inside, the grounds offer 36 acres to explore, including sculptures, lovely landscaping, scenic views and picnic tables. Note that pets may not be left unattended in cars or anywhere else for owners to enter the museum. 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

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

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

Enders State Forest

Granby, CT

Enders State Forest Enders State Forest in Granby is a dog-friendly recreational area in Granby, CT. This diverse forest spreads out over Granby and across to the nearby Barkamsted area, offering wetlands and waterfalls galore. Fido is welcome to join you in the picnic areas and on the hiking trails of this forest. 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

American Legion & Peoples State Forests

Barkhamsted, CT

American Legion & Peoples State Forests American Legion & Peoples State Forests are pet-friendly natural areas in Barkhamsted, CT. You can bring Fido with you to enjoy the beautiful, wooded areas and numerous trails as long as they are on a leash. This recreational area features trails ranging from less than a half mile to two miles for you and Fido to enjoy. 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

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

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

Monument Mountain Reservation

Great Barrington, MA

Monument Mountain Reservation Leashed dogs are allowed at Monument Mountain Reservation in Great Barrington, MA. This pet-friendly natural space features beautiful and moderately strenuous hiking trails. One trail reaches the 1,642-foot summit of the mountain and offers incredible Housatonic River Valley views. 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

The Bookloft

Great Barrington, MA

The Bookloft The Bookloft has been selling books in Great Barrington, MA, since 1974. Well-behaved, leashed dogs are welcome to join you as you select new books to read. You can even pull up a chair and read a book to your favorite furry friend. The shop sells dog treats as well. 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

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