Dog Friendly Activities in Sheffield, MA

There’s 1 dog friendly activity in Sheffield, 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 Sheffield.

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

Housatonic State Forest

Cornwall, CT

Housatonic State Forest Leashed dogs are welcome to explore parts of the Housatonic State Forest in Cornwall, CT. This pet-friendly recreation area boasts a variety of amenities for parkgoers, including hiking, hunting, letterboxing, mountain biking, snowmobiling and more. See Details

Familiar Trees

Great Barrington, MA

Familiar Trees Visit the dog-friendly Familiar Trees in Great Barrington, MA. Your leashed furry friend is welcome to join you inside this local bookshop, which offers a wide range of vintage and contemporary objects, art, and an extensive selection of books in the architecture, design, cinema, literature, non-fiction and photography genres. See Details

Becket Land Trust

Becket, MA

Becket Land Trust Becket Land Trust is a pet-friendly recreational hub in Becket, MA. Your leashed furry companion can tag along to explore over 300 areas. Established by a dedicated group of citizens, the park aims to preserve the town's rustic charm, safeguard its natural resources and conserve ecologically sensitive zones. Please keep your pup under control during your visit, and be aware that a parking fee is applicable. See Details

East Mountain State Forest

Great Barrington, MA

East Mountain State Forest East Mountain State Forest is a pet-friendly route in Great Barrington, MA. Your leashed canine companion can tag along as you hop on this challenging trip along the Appalachian Trail. The area features four beautiful overlooks with views of three states. Please note the terrain is rugged and that the area is a habitat for coyotes, bears, deer, and turkeys. See Details

Spencer's Run Dog Park at Waveny Park

New Canaan, CT

Spencer's Run Dog Park at Waveny Park Bring Fido to Spencer's Run Dog Park at Waveny Park for an afternoon of fun in New Canaan, CT. Dogs go wild for this 1.5-acre fenced, off-leash dog park, which includes trees for shade, benches for owners, water, and loads of room to run and play. This park is open to current registered members with a user code, and visiting canines must wear a license and current rabies tag. 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

Lee Premium Outlets

Lee, MA

Lee Premium Outlets Leashed dogs are welcome in outdoor spaces at Lee Premium Outlets, a pet-friendly outdoor shopping destination in the beautiful Berkshires of Lee, MA. Designed to mirror a quaint New England village, Fido is welcome in some of stores that feature pet-friendly stickers on their doors. Pups can even enjoy the on-site dog park. The recreational area contains two kennels, a water station, waste disposal station, and picnic table. You can find the dog park at the north end of the property near Bath & Body Works, Coach, and American Eagle Outfitters. See Details