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    Dog-Friendly Activities in Housatonic, MA

    There are 43 dog-friendly activities within 20 miles of Housatonic. 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 Housatonic.

    Pet Friendly Hilltop Orchards

    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
    Pet Friendly The Mount, Edith Wharton's Home

    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

    Bash Bish Falls State Park

    Mount Washington, MA
    Bash Bish Falls State Park Leashed dogs are welcome at Bash Bish Falls State Park in Mount Washington, MA. The centerpiece of the park, the stunning falls, are the highest single drop waterfalls in the state. You and Fido can view this natural wonder from the overlook or explore the area on the pet-friendly trails that weave around the park. 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

    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

    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

    Art Omi

    Ghent, NY
    Art Omi Art Omi is a pet-friendly, not-for-profit arts center with a 120-acre facility in Ghent, NY. Fido is welcome to tag along to explore the grounds and sculptures but must register for their dog pass program in the visitor center. Your furry friend can be off-leash in the architecture fields from October 1 until April 30 before 8:30 AM on weekdays. 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

    Forged Brewing Co.

    Bainbridge, NY
    Forged Brewing Co. 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. See Details

    French Park Dog Park

    Great Barrington, MA
    French Park Dog Park Fido can play off-leash at French Park Dog Park in Great Barrington, MA. This fenced dog park features two spacious, grassy areas and waste stations. Please bring water for Fido, and register on their website prior to enjoying the dog park. See Details

    Harlem Valley Rail Trail

    Copake, NY
    Harlem Valley Rail Trail The Harlem Valley 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 Copake! The map below shows a parking area with convenient access to the Harlem Valley 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. 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

    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

    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

    Taconic State Park

    Copake Falls, NY
    Taconic State Park Taconic State Park is a pet-friendly recreation area in Copake Falls, NY. You and your leashed dog can enjoy hiking the park's trails, camping, fishing, and picnicking. A maximum of two pets can join you at this park, and they must be supervised and on a six-foot or shorter leash throughout their visit. Pets aren’t permitted in buildings, playgrounds, golf courses, boardwalks, pools, spray grounds or guarded beaches. Please clean up after Fido. 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

    Beartown State Forest

    Monterey, MA
    Beartown State Forest Leashed dogs are allowed at Beartown State Forest in Monterey, MA. Home to a 12,000-acre forest and Benedict Pond, you and Fido can take on the pet-friendly Benedict Pond Loop Trail, which circles the scenic pond. Although a nice location year round, one of the best times to visit is in autumn to enjoy the breathtaking fall foliage. See Details

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    Housatonic, MA, US