Dog-Friendly Activities in Otis, MA

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.

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Campbell Falls State Park Reserve is a pet-friendly recreational area in Norfolk, CT. This natural area offers plenty of hiking experiences for you to enjoy with your dog. Just keep Fido on a leash at all times.

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.

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.

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.