The Berkshire Mountains region in Massachusetts is known for its stunning natural beauty and plethora of outdoor activities. If you are considering a vacation with your family (including the four-legged members), there are plenty of accommodations and things to do in the pet friendly Berkshire Mountains, no matter what the season.

The Berkshires is a hilly region in the western-most part of Massachusetts, stretching north to the Vermont border and south to Connecticut. To the west is New York State, and to the east a ridge of hills over which runs the Appalachian Trail. The region includes 30 mainly rural towns and two small cities, Pittsfield, The Berkshire County seat and North Adams. The Berkshire Mountains are equidistant from Boston – about 120 miles east – and New York City – about 120 miles southwest, or a two to two-and-a-half-hour drive.

The history of the area boasts a tradition of arts and letters from the 19th century, with famous American authors such as Herman Melville and Nathaniel Hawthorne, who resided in the area, and Henry David
Thoreau, whose visits to the Berkshires are well-documented. In the early 20th century, this was home to Edith Wharton, who built a summer estate called, simply, The Mount. This was also the summer getaway for the rich and powerful during the Gilded Age, when many of the luxurious Berkshire “Cottages” were built. These summer homes were, in fact, grand homes for residents of metropolitan. New York who spent summers here at the turn of the 20th century.

Springtime in the Berkshire Mountains

In the springtime, the Berkshires burst with new life. Snow dissolves into mountain streams, and the scent of springtime-of fresh flowers and rich soil-fills the air. A host of new activities in the Berkshires come to life as well. You can golf, bike, stroll through botanical gardens or budding forests, ride horses or llamas, visit antique shops, historical homes and museums, and much, much more.

Summertime in the Berkshire Mountains

The Berkshires truly come alive in the summer. Tanglewood brings classical concerts to music lovers beneath the stars (no pets allowed on the grounds, though). Museums feature new shows and world-class artists-both time-honored and cutting-edge spectacular mountains, beautiful forests, pristine ponds and rushing streams beckon lovers of the outdoors to camp, hike, bike, raft, fish, swim, boat and golf. Theatre festivals offer traditional and contemporary performances, from Shakespeare to Sam Shepard. Picturesque downtown villages host community parades and festivals.

Though farmers offer a colorful array of fruits and vegetables from May through the holiday season, it’s the cool autumn months that give a hearty robust flavor to fresh pumpkins and apples. A scenic drive along a backcountry road will most likely lead to a farm where you and your family can pick your own.

Outdoor activities during the spring and summer abound. The Berkshire Mountains are home to numerous parks, trails, and outdoor recreational areas where you can enjoy nature with your pet. Some trails do close in the winter months, so check this before you go.

You should bring your pet’s leash along as most all trails will require that your pet be leashed. Popular pet-friendly parks and trails include:

• Kennedy Park (Lenox, MA)
• Mount Greylock State Reservation (Adams)
• Ashuwillticook Rail Trail (Cheshire to Lanesborough)
• Pittsfield State Forest (Pittsfield, MA)
• Monument Mountain Reservation (Great Barrington, MA)
• Beartown State Forest (Monterey, MA)
• Mount Washington State Forest (Mount Washington, MA)
• October Mountain State Forest (Lee, MA)
• Hilltop Orchards (Richmond, MA)
• Bash Bish Falls Trail (Mount Washington, MA)

For “spirited” pet owners, check out these pet-friendly wineries:

• Balderdash Cellars (Richmond, MA)
• Home Range Winery (Canaan, NY)
• Hilltop Orchards (Richmond, MA)
• The Cambridge House Brew Pub (Granby, CT)
• Les Trois Emme Winery and Vineyard (Marlborough, MA)

Autumn in the Berkshire Mountains

When autumn arrives in the Berkshires, it means harvest time is here. The scent of fresh baked pies is in the air and pumpkins and apples are ready for the picking. The Berkshires are bountifully blessed with luscious, locally grown produce.

Stunning vistas become even more spectacular, as gold, yellow, and scarlet hues blanket the landscape. Mountains glimmer in the sun. Spend your days outdoors in the golden kaleidoscope-hiking, biking, picking apples and pumpkins. Embrace the views as you drive to museums, antique shops and cultural events.

The following museums will allow leashed pets on their grounds:

• Norman Rockwell Museum
• The Mount, Edith Wharton’s Home
• Herman Melville’s Arrowhead
• Ventfort Hall and Gilded Age Museum

Because the Hancock Shaker Village has various animals in their attraction, pets are not allowed. The Massachusetts Museum of Contemporary Art also does not allow pets.

Winter in the Berkshire Mountains

In the Berkshires, wintertime means playtime. In other parts of the world people hibernate during the cold weather, but in the Berkshires, the fun is just beginning. You can ski or snowboard at one of our many ski resorts, explore miles of cross-country trails, visit historic downtowns illuminated by twinkling holiday lights and hike through still, serene forests.

Of course, there are plenty of tempting indoor pursuits as well: Take a leisurely stroll through your choice of museums, indulge yourself with a luxurious health spa visit or have a shopping spree at any of the Berkshires many different merchants. And when the winter day is done, warm your soul with a sumptuous dinner out, then snuggle into a cozy bed in one of a host of legendary lodging facilities.

Pet Friendly Accommodations in the Berkshire Mountains

Many hotels, motels, inns, and vacation rentals in the Berkshire Mountains area are pet friendly. Be sure to check with individual accommodations about their pet policies and any additional fees. Some popular pet-friendly options include:

• Red Lion Inn (Stockbridge, MA)
• The Porches Inn at Mass MoCA (North Adams, MA)
• Ventford Hall (Lenox, MA)
• Jiminy Peak Mountain Resort (Hancock, MA)
• The Williams Inn (Williamstown, MA)
• The Black Swan (Lee, MA)
• Vacation rentals through Airbnb or Vrbo often offer pet-friendly options as well.

Augusta House is a charming, pet friendly, 1863 Colonial conveniently located on a quiet street in the beautiful hill section of Great Barrington. It is surrounded by other elegant historic homes, only a few minutes’ walk to downtown Great Barrington, one of the wonderful towns nestled in the Berkshires. A day or evening stroll will bring you to shops, restaurants, and entertainment. Great Barrington was incorporated in 1761 and is a quaint town with enough activity to keep you and your pet interested.

For those of you who enjoy the supernatural, the innkeepers of the Wainwright Inn report hearing people singing and seeing lights turn on and off. Alarms in the hallways sometimes go off for no reason, and they’ve also heard unexplained footsteps in the attic above their living space.

It is always best to understand all pet policies regarding pet areas, leashing, waste removal and other considerations wherever you visit in the pet friendly Berkshire Mountains. Enjoy the adventures with your best friend! It will be worth the trip.