Dog-Friendly Things to Do in the Berkshires

The Berkshires Is for Everyone, Including Your Four-Legged Friends!

Whether your pup is a serious hiker, a professional patio lounger, or simply very good at convincing you to share your snacks, you’ll find plenty of ways to enjoy the Berkshires with your dog. Grab the leash, pack the treats, and get ready for a pawsome adventure.

Stay Somewhere That Welcomes the Whole Family

Finding a place to stay is a little easier when your definition of “the whole family” includes someone with paws. The Berkshires has pet-friendly lodging throughout the region, from cozy inns and boutique hotels to outdoor-focused stays and vacation rentals.

In North Adams, TOURISTS offers an outdoorsy take on the classic hotel stay. In Pittsfield, Hotel on North puts you right in the heart of downtown and welcomes pets on its designated pet-friendly floor.

Further into North and Central County, other pet-friendly options include Berkshires Untold, which welcomes dogs, and Huttopia Berkshires, where you can get a little closer to nature with a glamping experience.

Heading south? Element Lenox Berkshires offers pet-friendly accommodations in Lenox and the surrounding area. In Great Barrington, The Little Lion offers another welcoming option for travelers exploring South County with their four-legged companions.

Want to get a little closer to nature? Huttopia Berkshires offers a glamping experience surrounded by the outdoors, without quite having to commit to sleeping on the ground.

Browse our pet-friendly lodging listings to find a place that works for both you and your travel companion.

Pet policies, fees, size restrictions, and the number of pets allowed vary by property and can change. Be sure to check directly with your lodging provider before booking.

Go Where the Trails Are

If your dog gets noticeably more excited when they see a hiking boot, you’re in the right place.

The Berkshires is home to hundreds of miles of trails, with everything from easy walks to challenging mountain hikes. And there’s no shortage of scenery to sniff along the way.

For an easy-going outing, head to the Ashuwillticook Rail Trail, a mostly level, multi-use trail winding through Pittsfield, Cheshire, Lanesborough, and Adams. It’s a great choice for a leisurely walk, a bike ride, or simply letting your dog investigate approximately 7,000 extremely important smells.

Looking for a bigger adventure? Explore Mount Greylock State Reservation or Greylock Glen in Adams. With mountain scenery, forests, and plenty of trails to choose from, it’s classic Berkshire hiking at its best.

For even more places to explore with your dog, visit Berkshires Outside for ideas on getting outdoors throughout the region.

Before heading out, check current trail conditions and posted rules, and remember that some trails have seasonal restrictions.

Art, Culture & a Little Downtown Wandering

Your dog may not have much to say about the Impressionists, but that doesn’t mean they can’t enjoy the Berkshires’ arts and culture scene.

At The Clark Art Institute in Williamstown, leashed dogs can explore 140 acres of lawns, meadows, and walking trails surrounding the museum. Take a stroll around the reflecting pool, wander up Stone Hill, and enjoy the views. Just save the galleries for your human companions.

At The Mount, Edith Wharton’s historic Lenox home, leashed dogs are welcome to explore the grounds and gardens. Several trails wind through the property, making it a beautiful spot for a walk.

You can also spend an afternoon exploring the charming streets of Stockbridge, where a downtown stroll can easily turn into an afternoon of shops, snacks, and people-watching. Your dog will probably be especially interested in that last part.

Many Berkshire cultural attractions have outdoor spaces where dogs are welcome, even when pets aren’t permitted inside. Always check individual policies before visiting.

And don’t forget the souvenirs. Barkshire Dog Trading Co. has Berkshire-inspired gear and gifts for pups and their people, including plenty of ways to commemorate your trip.

Find a Patio and Call It Lunch

After a hike, there is only one reasonable thing to do: eat. Plenty of Berkshire restaurants, cafés, breweries, wineries, and farms offer outdoor spaces where dogs can join their people. Look for patios and alfresco dining when planning your meals, and always check the current policy before you go.

At Balderdash Cellars in Richmond, dogs are welcome in the outdoor areas, where you can settle in with a glass of wine and enjoy the views.

Plan a stop at High Lawn Farm in Lee, where leashed dogs are welcome in outdoor areas. Be sure to grab a farm-fresh ice cream cone for yourself and a pup cup for your four-legged friend.

Bright Ideas Brewing in North Adams is another great stop for an outdoor drink with your pup after exploring downtown.

You’ll find even more dog-friendly patios and outdoor dining options throughout the Berkshires, so there’s no need for anyone to sit this meal out.

Ready to Explore the Barkshires?

The Berkshires has plenty of room for you, your dog, and probably a stick or two that absolutely must come home with you.

And when you’re ready to plan the rest of your trip, check out the Official Guide to the Berkshires for even more places to stay, play, dine, and explore.

Bring the leash. Pack the treats. Leave a little room in the itinerary for a good sniff.

We’ll see you and your furry friends #intheberkshires!