The Barkshires Trail

In the Berkshires, we love dogs! Travelers with furry friends will find tail-wagging welcomes at many of our lodging properties, downtown shops, alfresco dining establishments, and even some of our cultural grounds. Follow this trail for a few stops that are sure to be Fido’s new faves.

ROAM: A Xtina Parks Gallery (Williamstown)

Love styling your pup for your shared adventures? Find pet collars and leashes studded in traditional Maasai beadwork that are handcrafted in Kenya at ROAM, an African fair-trade shop and gallery of fine art and photography. At this flagship location you’ll find clothing, home decor, jewelry, and pet accessories – all handmade and beautifully curated.

The Clark (Williamstown)

You and your pup can romp across The Clark’s beautiful 140 acres of expansive lawns, meadows, and walking trails for free year-round. Start your stroll by the reflecting pool, then hike up Stone Hill for a spectacular view of the mountains. Well-behaved pooches can run off leash across the meadows and through the woodlands, but watch out for cows (and their souvenirs!) – part of the property’s enclosure is an outdoor sculpture called “Teaching A Cow How to Draw” by artist Analia Saban. Don’t miss taking a selfie with your pup inside Thomas Schütte’s “Crystal.”

Balderdash Cellars (Pittsfield)

Sip wine with a spectacular view at Balderdash Cellars while your pup naps next to your Adirondack chair at this local winery helmed by a friendly Berkshire couple. Food trucks are often onsite for snacks to accompany your tasting flights. In the summer, try a wine slushy!

Balderdash Cellars. Photo by Great Sky Media.

Shakespeare & Company (Lenox)

Attend a canine-friendly performance of Romeo & Juliet with Shakespeare & Company outdoors at the Arthur S. Waldstein Amphitheatre on Sunday, August 3,2025. Treats will be on hand and complimentary canine companion seating will be available for large dogs. All pups must be leashed and well-behaved. Patrons without dogs are also welcome!

Downtown Stockbridge  (Stockbridge)

Stroll one of the Berkshires’ most iconic downtowns where all dogs are welcome. Sip an iced tea or hot cider on the porch of the famed Red Lion Inn with your pup at your feet, or grab a scrumptious pastry, fresh sandwich, or double scoop of ice cream to snack on as you and your pup people-watch from a picturesque sidewalk bench. Then enjoy the beautiful Berkshire hills as you explore the grounds of the Norman Rockwell Museum – just leave pups at home if you plan to take in the exhibitions or shop the gift store. 

Robin’s Candy (Great Barrington)

No matter your age, you can be a kid in a candy shop at Robin’s Candy in Great Barrington – and your dog can be part of the fun! Dogs on leashes are welcome in the store where you’ll find a curated collection of classics and “classics-in-the-making.” Savor your sweets while you stroll down Main Street through one of the Berkshires’ most quintessentially New England downtowns lined with boutiques, galleries, and restaurants.

High Lawn Farm (Lenox)

Treat yourself to a farm-fresh ice cream cone or some artisanal cheese at High Lawn Farm’s Farmstead Creamery, where leashed dogs are welcome in outdoor spaces and barns. Chill at a picnic table while the Jersey girls graze or walk around the idyllic grounds. Before or after, go exploring in Lenox – many of the shops are dog-friendly and restaurants often have outdoor seating.

Explore more Barkshire inspo! From Pup-loving Lodging to Dog-friendly Adventures to Pet Care #intheberkshires, we have you and your furry friend taken care of!