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    Dog Friendly Activities in Pittsfield, MA

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    There are 3 dog friendly activities in Pittsfield, and 36 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 Pittsfield.

    Pet Friendly The Bookloft

    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
    Pet Friendly Tolland State Forest

    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

    Clarksburg State Park

    Clarksburg, MA
    Clarksburg State Park Leashed dogs are allowed at Clarksburg State Park in Clarksburg, MA. This pet-friendly park is especially popular during the fall months, when the trees offer stunning colors as the leaves change. There are a number of trails for you and Fido to explore, some that even follow along a scenic lakeshore. See Details

    Stone Hill Trails

    Williamstown, MA
    Stone Hill Trails Dogs are welcome to join you as you explore the pet-friendly Stone Hill Trails in scenic Williamstown, MA. This relatively easy and short hike offers excellent views of the area and, while it is recommended to leash your pup there are many dogs that hike this area off leash. The easiest way to access the trails is to park at the Clark Art Institute Visitors Parking, head towards the Lunder Center parking and begin your hike on the gravel trail to the east. See Details

    Hopkins Memorial Forest

    Williamstown, MA
    Hopkins Memorial Forest Leashed dogs are welcome at Hopkins Memorial Forest in Williamstown, MA. This pet-friendly reserve encourages educational and low impact activities that celebrate understanding and enjoyment of the environment. Fido can explore the scenic trails with you throughout the area. See Details

    Ashuwillticook Rail Trail

    Cheshire, MA
    Ashuwillticook Rail Trail The Ashuwillticook 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 Cheshire! The map below shows a parking area with convenient access to the Ashuwillticook 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

    Farnsworth Fine Cannabis Company

    Great Barrington, MA
    Farnsworth Fine Cannabis Company Farnsworth Fine Cannabis Company is a dog-friendly recreational marijuana dispensary in Great Barrington, MA. Fido is welcome to join you as you peruse the upscale space that was featured in Architectural Digest's list of the "most stylish dispensaries in the country." See Details

    Love's Travel Stop

    Canaan, NY
    Love's Travel Stop Love's Travel Stop in Canaan, NY, is a dog-friendly gas station and rest area. Across America, you'll find Love's Travel Stops that offer facilities for traveling canines. This location has a fully-fenced dog park with a convenient waste station. See Details

    Monroe State Forest

    Shattuckville, MA
    Monroe State Forest Leashed dogs are welcome at Monroe State Forest in Shattuckville, Monroe and Florida, MA. This pet-friendly forest offers views of stunning valleys and waterfalls. Fido can join you as you hike to the top of Spruce Mountain or Raycroft Lookout, with some of the most breathtaking views in the area. Please note that there are multiple parking locations depending on the trailhead you are visiting. See Details

    Windsor State Forest

    Windsor, MA
    Windsor State Forest Leashed dogs are welcome at Windsor State Forest, a pet-friendly natural space in Windsor, MA. Visitors are drawn to this pretty park for the views of the Berkshire Hills. You and Fido can explore the area together, including Windsor Jambs waterfall and the Windsor Jambs Brook that weaves through a wide gorge with 80-foot granite walls. See Details

    North Adams Dog Park

    North Adams, MA
    North Adams Dog Park Bring Fido to the North Adams Dog Park in North Adams, MA. This dog park is fenced in to allow for off-leash play, with separate areas for small breeds and large breeds to ensure that all pups have fun. Please remember to keep Fido on a leash when outside of the fenced 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

    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

    Cherry Plain State Park

    Petersburgh, NY
    Cherry Plain State Park Leashed dogs are welcome at Cherry Plain State Park, a pet-friendly recreation area in Petersburgh, NY. You and Fido can enjoy hiking, biking and cross-country skiing the park's trails. Boating, fishing and camping are also popular. You can bring a maximum of two pets and they must remain on a six-foot or shorter leash throughout your entire visit. Proof of a current rabies vaccination must be present. Pets aren't permitted in playgrounds, buildings, golf courses, boardwalks, pools and spray-grounds, or guarded beaches. Please clean up after Fido. 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

    Peru State Forest

    Peru, MA
    Peru State Forest Peru State Forest is a pet-friendly attraction in Peru, MA. Your furry companion can tag along to enjoy this oasis. Activities include hiking, birdwatching, camping, fishing and picnicking. Trails wind through stunning landscapes, streams, crystal-clear ponds and more for all endurance levels. Please ensure Fido remains on a leash during your adventure. 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
    Pittsfield, MA, US