BringFido’s Guide to The Berkshires

Posted by Billy Francis

The Berkshires sprawl across parts of western Massachusetts into northwest Connecticut. This hilly region of New England has long been known to attract famous authors and artists looking to escape the distractions of big city life, but they’re not the only ones who have flocked to these scenic surroundings for a breath of fresh air. Four-legged travelers can join their owners in The Berkshires to explore historic grounds, hike into the clouds and visit charming towns.

Things to Do

Unleash the fun. Photo by

The “Barkshires” are calling you and your cultured canine.

Waterfall Hike

Bash Bish Falls State Park. Outbound hounds will love the pet-friendly out-and-back trail that leads to viewing points of the highest single drop waterfall 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.

Take a Walk Through History

Escort Fido on a self-guided tour of the grounds of The Mount, Edith Wharton's Home in Lenox, MA. Edith Wharton published more than 40 books over a 40-year career to become one of America’s greatest writers. In addition to writing novels, she also designed her house and beautiful grounds. Dogs aren’t allowed inside, but are welcome to tour the sunken Italian garden and pathways free of charge.

Reach the Highest Point in The Bay State

Drive or hike with your hound to the highest point in Massachusetts, Mount Greylock State Reservation. On a clear day, visitors can see almost 90 miles of the surrounding area from its peak and can always enjoy Mount Greylock Monument. To reach the summit, you and your hiking buddy can climb a moderate 7-mile trail or drive the 16-mile scenic byway.

Visit Melville’s Place With Your Mutt

Supposedly, writer Herman Melville got the idea for the white whale in “Moby Dick” from seeing Mount Greylock State Reservation covered in snow. After visiting the place that inspired his greatest work, see where he wrote it at Herman Melville’s Arrowhead. Dogs are not allowed inside the house, but the 45-acre grounds and nature trails are open year-round for hiking, snowshoeing, and cross-country skiing at no cost.

“This is nice. Now, how do I get out?”Photo by @rogerdawg

Pick Fruit With the Apple of Your Eye

Hilltop Orchards is a family-run property that sits on 200 acres and grows 26 varieties of apples, most of which are available for visitors to pick. During apple season, they offer free hayrides for two- and four-legged guests alike. Hilltop Orchards also allows visitors with pets to use their land for hiking, skiing and snowshoeing. Apple season at Hilltop Orchards usually runs from Labor Day through Columbus Day.

Calling All Canine Critics

Get inspired on a walk around TurnPark Art Space in West Stockbridge, MA. This outdoor art park welcomes dogs to join their owners on a sculpture walk around 16 acres of land on the site of a former quarry. Art on display includes work by Alexander Konstantinov and others. From views of rolling hills, meadows and a lake, natural beauty is the real masterpiece at TurnPark.

Paddle With Your Pup

The Berkshires has an abundance of freshwater lakes and waterways compared to other parts of The Bay State. Berkshire Canoe Tours offers a dog-friendly tour on the quiet Housatonic River. While you paddle with your pooch, you may be lucky enough to see hawks, owls, beavers and more.

Places to Stay

"Follow me to your room." Photo by @jessmarchione

Historic hotels, cozy homes and romantic retreats await you and your pooch in the rolling Berkshire Hills.

There’s Room at the Inn

The Red Lion Inn is a charming place to hang Fido’s leash in Stockbridge, MA. The inn is made up of village houses, a large guesthouse, and a number of unique lodging options for you and your dog. Four-legged guests are greeted with treats and bowls at check-in. During your stay, visit the pet-friendly gardens of Norman Rockwell Museum located just a short walk away.

Escape to the Lake

Enjoy a vacation home with its own private lake at this spectacular Berkshire retreat in Lee. Whether your pooch loves to swim, cross-country ski or hike, there’s something for all active dogs here. If he prefers the laid-back life, simply admire the natural show when the leaves start to turn a different color during fall.

Get Cozy Around the Fire Pit

Reserve a stay at this cozy home in Becket with your best friend. This cute little house has a great outdoor space, which includes a grill, dining area and a fire pit to gather around and cook s’mores for the family. Don’t forget to bring your ice skates along to glide across nearby Big Robin Lake when it freezes over in winter.

“We’re smiling on the inside.”Photo by

Motel at Monument Mountain

Located at the foot of Monument Mountain in Great Barrington, The Briarcliff Motel provides an affordable place for traveling canines and their owners who want to experience The Berkshires, but aren’t interested in spending big. At dinnertime, walk into town and enjoy Greek delights at the pet-friendly Aegean Breeze.

Pitch Up in Pittsfield

Pittsfield is the biggest city in The Berkshires and makes a great jumping off point before you head further into the hills. Reserve a stay at Hotel On North, a 4-star hotel downtown. Each room has been carefully and uniquely decorated to compliment the exposed brick dating from the 1880s. Sip cocktails with your Cockapoo in a birdcage elevator at this delightful pet-friendly hotel. Pittsfield Dog Park is a short walk away.

Stay in a Striking Family Home

Nestled in the woods near The Appalachian Trail, this beautiful Berkshire family house is immersed in nature. The high beams, tall ceilings and sunny rooms will make it difficult to drag yourselves away to all the sights in the surrounding area. If you end up staying in for the day (or week), curl up with a book in front of the roaring fireplace.

Share a Welcoming Village Stay

Surrounded by rolling fields and meadows, The Old Inn On The Green is a picturesque place to rest after a long day of exploring The Berkshires. There’s plenty of room around the historic former stagecoach relay to stretch Fido’s legs before bedtime. The attached restaurant has even been known to provide pup cups on summer days.

Dog-Friendly Restaurants

“You can’t beat the brewery!” Photo by @bugz_harishdottir

Whether you’re looking for a sunset dinner or a morning pick-me-up, The Berkshires delivers on dining out with your furry foodie.

Say “Cheers!” in Barrington

Relax and refuel on the pet-friendly patio of the expansive Barrington Brewery. Locals and tourists alike enjoy ordering a round of beers brewed on the premises and soaking it up with burgers, wings and other freshly made bites.

Sample Locally Sourced Delights

Dotties Coffee Lounge is proud to source food locally. Bring your dog along to sit on the patio while you enjoy breakfast sandwiches and a variety of specialty coffee drinks. This local hangout hosts a variety of events throughout the year to bring the community together.

Enjoy Baked Goods With Your Good Boy

For a casual bite, look no further than Haven Cafe & Bakery in Lenox. This local staple serves up fresh breakfast, lunch and weekend brunch. Sink your teeth into creative morning fare like a breakfast sandwich on challah bread or a breakfast banh mi. Leashed dogs are welcome on the expansive patio area.

Pretty in purple. Photo by @heather.runs

Pints at a New England Pub

When The Purple Pub in Williamstown swings the doors open during the summer months, it’s hard to walk by without stopping in for a pint or two. Dogs are welcome on the patio to meet local mutts who frequent this popular spot.

Pinot With Your Pup

Get a taste for Massachusetts' wine scene at Les Trois Emme Winery and Vineyard. Bring your best friend to this family-owned vineyard, where you can sample five different Les Trois Emme wines in the tasting room. Afterwards, enjoy a walk through the grounds to see how the grapes are grown.

Peace, Love and Ice Cream

There’s nothing quite like an ice cream to cool off on a hot summer’s day, right Fido? Join the ice cream fanatics at Ben & Jerry’s in Pittsfield for a refreshing and flavorful scoop for you and one for your pooch, too.

Merlot With Your Mutt

If you don’t mind Fido staring wistfully at you while you eat, grab a table on the covered patio at Brava in Lenox. Choose from a selection of tapas, pizzas, and cheese plates while you sip on delicious wines from the bar.

What are your favorite dog-friendly things to do in The Berkshires? Leave a comment or tweet us @BringFido!

Banner photo by @zekeohzeke.