Remarkable East Coast Ski Destinations: The Berkshires, Massachusetts

The first of a four-part series exploring remarkable ski destinations

The Berkshires region of Massachusetts is situated perfectly between the large cities of New York and Boston; making it the perfect northeast getaway for those who want to escape the city—its rolling hills and scenic countryside provide a plethora of outdoor activities all year long; while its art, culture, and history add a city-like sophistication that pairs well with its rustic charm. Truly the best of both worlds—a multitude of eclectic diversions and activities; and a scenic haven for nature lovers—the Berkshires are sure to captivate any visitor looking for a relaxing, yet fun, getaway to New England.

Winter is an especially enchanting time in the region, as the warm weather activities of hiking, biking, fishing, and water sports give way to some of the best opportunities for winter recreation in Massachusetts—including five well-regarded ski areas, and a myriad of places for snowshoeing, cross country skiing, and sledding. The best part is, there is still plenty to see and do in this picturesque region after you put your skis away for the day; whether its relaxing by exploring one of the area’s quaint New England towns; or unwinding by the fire with a warm drink while soaking up the unforgettable Berkshires scenery.

Explore The Berkshires’ Charming Small Towns

The Berkshire region consists of several small towns, each more charming than the last. Each place has its own distinctive vibes—yet all are brimming with the small town charm and welcoming atmosphere the area is famous for. And all of these amazing towns are within an hour and a half or less of one another, making the region infinitely explorable; whether you’re looking for a weekend getaway or a week long retreat, the Berkshires has something for everyone.

Christmas in downtown Stockbridge, Photo Courtesy of the Stockbridge Chamber of Commerce

Pittsfield: The Largest City In The Berkshires

Pittsfield is the largest city in the Berkshires and is in the heart of the region; designated the “City of Festivals,” it’s a top spot to explore the area’s top cultural offerings. It’s also home to a number of celebrations and fun events throughout the year throughout the downtown area. There’s no shortage of recreation here too—with a number of parks and outdoor opportunities that even include their own baseball team, the Pittsfield Suns.

Almost all of Pittsfield’s downtown area is dedicated to its diverse range of cultural attractions, supplemented with numerous dining, shopping, and recreational amenities.

Family Fun in Pittsfield

The Hub Of South County: Great Barrington

Great Barrington is the jewel of the Southern Berkshires—its vibrant and bustling downtown area is chock full of history, culture, and above all, charm. Known as a city of ‘firsts,’ Great Barrington’s Main Street was one of the first in the country to have electric lights; its Railroad Street is one of the oldest in the U.S., and it boasts the site where the first slave was freed. With an abundance of history, a fashionable shopping and dining district, and numerous outdoor activities including hiking and cycling in the summer, and skiing in the winter, it’s no surprise Great Barrington was voted the #1 Best Small Town by Smithsonian Mag in 2012.

Where To Stay in Great Barrington

Where To Eat in Great Barrington

Merrell Inn, Lee, MA

Lee: The Gateway To The Berkshires

Since the 1760s, the town of Lee has been a historic haven for visitors to the region. Known as the Gateway to the Berkshires, Lee was named after famed revolutionary patriot General Charles Lee. In this over 250-year old gem history reigns supreme—and there are plenty of testaments to its long and storied traditions throughout its downtown area that’s listed in the National Register of Historic Places. But Lee isn’t just about history—the town is about the present, too; focusing on revitalization projects to bring more restaurants, shopping, and attractions to the area.

Where To Shop in Lee

Lenox: Brimming With New England Charm

The former home of literary giant Edith Wharton, the charming hamlet of Lenox is known for both its scenic, recreational areas and its distinctive downtown full of architectural and historical landmarks. Stroll through the tree-lined avenues and scope out this quaint Berkshire town that’s also home to national attractions like Kripalu and Tanglewood, and was named the Best Northeastern Small Town by USA Today in 2017.

Where To Dine in Lenox

The Charming Towns Of North Adams And Williamson

These two Berkshire towns are renowned for their scenic natural beauty that includes two famed state parks. North Adams is known as ‘The Town of Steeples and Peaks’ because of its rolling forests and hills, proximity to Mount Greylock (the state’s tallest summit), and its abundance of charming village churches that add to the quaint, charming backdrop. Also home to the largest contemporary art museum in the country, The Massachusetts Museum of Contemporary Art (MASS MoCA), the area also has plenty of cultural significance.

Williamstown is also an idyllic combination of lovely scenic sights and diverse cultural attractions. Known as ‘The Village Beautiful,’ it is a picture of Berkshire beauty and charm. Home to natural treasures such as the Hopkins Memorial Forest, the Taconic Trail State Park, and the Bullock Forest; the town is also a bastion for the arts where visitors can explore some of the region’s most iconic attractions—such as the world famous Williamstown Theatre Festival.

Outdoor Adventures in North Adams and Williamstown

Winterfest in downtown North Adams, Photo Courtesy of the Mohawk Trail Association

Stockbridge: Picturesque And Historic

In the heart of the Berkshire Hills lies the picturesque town of Stockbridge. Famous for being the long-time residence of American icon Norman Rockwell, who immortalized the town in his famous painting ‘Stockbridge Main Street at Christmas.’ There’s even a Rockwell museum—home to the world’s largest collection of his art. Explore the charming downtown area that has remained largely unchanged throughout the years, and revel in the New England village vibes. Check out the area’s many recreational pursuits that include famous trails along the Housatonic River, and access to world-class skiing. Most of all, bask in this historic hamlet that is the epitome of small-town Berkshire charm.

Historic Sites in Stockbridge

Christmas in downtown Stockbridge, Photo Courtesy of the Stockbridge Chamber of Commerce

Skiing In The Berkshires

The Berkshires are a bastion for some of the best winter recreation in the Northeast. Home to five top ski areas and full of numerous opportunities for a variety of cold-weather activities like cross-country skiing, snowshoeing, sledding, and more; outdoor enthusiasts and winter sports fans will find plenty to celebrate in this scenic New England tourist destination.

Berkshire East Mountain Resort

A favorite of both locals and tourists alike, the Berkshire East Mountain Resort is a family-owned ski area that has been providing outdoor recreation in the Berkshires for over 40 years. It’s also the only ski area in the world to produce 100% of its energy from onsite renewable energy, making it super eco-friendly, too. And for those that want to hit the slopes without skis, Berkshire East also has an epic Snow Tubing Center for epic winter fun.

Berkshire East is also a four-season resort where visitors can enjoy lovely accommodations with views of the surrounding mountains—all while enjoying the most skiable terrain in Massachusetts. A true Berkshires mountain getaway for the entire family, this epic lodge also has several on-site restaurants and pubs that make it a truly inclusive winter getaway. And with 45 trails to choose from, everyone from beginners to experts can hit the slopes when the 2021-2022 season commences in mid-December.

Lifts and Trails at Berkshire East

Where To Eat At Berkshire East

Photo Courtesy of Berkshire East Mountain Resort

Bousquet Mountain

“The Berkshire’s Local Mountain since 1932,” Bousquet Mountain has long been a favorite winter haven for skiers and winter sports enthusiasts everywhere. Close to downtown Lenox, this picturesque ski area is close to a number of area attractions for those who want something to do after hitting the slopes. Home to the Yokun Terrain Park, 8 lanes of snow tubing fun, and 18 epic trails, this historic ski area is full of plenty of activities for the entire family.

Lifts and Trails at Bousquet Mountain

Where To Stay and Eat: Bousquet Mountain

Catamount Mountain Resort

Snowmaking is the focus at Catamount Mountain Resort—known as being one of the best snow making operations in Southern New England, making it the perfect spot to catch the best conditions during the season. New this year to Catamount is a snow tubing center where visitors of all ages can have a blast on the resort’s super-fast tube that’s groomed to perfection. Known as one of the most diverse trail networks in the Berkshires, Catamount’s 43 trails are perfect for skiers and riders of all skill levels. Catamount is the sister resort to Berkshire East, and it offers similar accommodations at its new and improved lodge. There are also several restaurants on-site for visitors to enjoy; and for those planning a single day trip, cabanas are available to rent to store your gear while spending the day on the slopes.

Lifts and Trails at Catamount

Where To Eat At Catamount

Berkshires Skiing at its best, Photo Courtesy of Catamount Mountain Resort

Jiminy Peak Mountain Resort

A family-friendly ski resort with plenty of activities, the Jiminy Peak Mountain Resort has over 150 acres of top-notch skiing and snowboarding trails. One of Southern New England’s favorite ski resorts since 1948, Jiminy now runs on 100% renewable energy sources, making it an eco-friendly and fun place to be. For those who like to hit the slopes after dark, Jiminy also offers 21-night skiing riding trails lit by LED lights where visitors can hit the mountain under the lovely New England sky. Comfortable, cozy lodgings are available on-site, so visitors don’t have to worry about traveling and can spend more time outside. Also available on-site are restaurants, shopping, and other activities and entertainment—an all-inclusive resort experience with something for everyone to enjoy.

Trail and Lift Map of Jiminy Mountain

Shopping and Dining at Jiminy Creek

Activities at Jiminy Creek

Ski Butternut

Close to the lovely town of Great Barrington, Ski Butternut is located on the northern slopes of the East Mountain State Forest. This incredibly scenic resort is relaxing and peaceful—nestled among the area’s sprawling evergreen and hardwood forests. For almost 60 years, Butternut has provided a fun, memorable ski experience for both locals and visitors alike. And Butternut isn’t just for skiing—the resort also offers epic tubing opportunities; two lodges with several dining options; and an on-site ski and board shop.

Trails and Lifts at Ski Butternut

Where To East at Ski Butternut

Where To Stay Near Ski Butternut

Learning to Ski, Photo Courtesy of Ski Butternut

Other Winter Recreation In The Berkshires

While the Berkshires is famed for its skiing, there are also a plethora of other outdoor activities for visitors to enjoy when not hitting the slopes. Cross country skiing is a popular winter past-time in New England, and the Berkshires also has its fair share of beautiful spots to choose from. Canterbury Farm is a charming bed and breakfast where visitors have access to ice skating, cross-country skiing, and snowshoeing—the perfect spot for those who love being outside in the chill Massachusetts air. While lodging is only open during the summer months, this lovely spot is still open to visitors who want to visit this hidden gem in nearby Becket, MA.

Another popular spot to cross-country ski, snowshoe, and even take winter hikes is the Northfield Mountain Recreation & Environmental Center. Located on the picturesque mountainside in nearby Northfield situated along the Connecticut River, Northfield is the perfect spot for outdoor enthusiasts to enjoy over six miles of snowshoe trails.

Trail Map of Northfield

For those who aren’t fans of skiing, there are still plenty of ways to enjoy the beautiful scenery in the Berkshires; ice skating and sledding are two extremely popular winter activities that people also enjoy when visiting this picturesque Massachusetts region.

Where To Ice Skate

Where To Sled

The Berkshires are the perfect four-season destination—full of outdoor activities throughout the year and set among the stunning mountainous backdrop and forested green hills of western Massachusetts, the area’s scenic beauty is one of the top reasons this lovely New England region is a top tourist destination.

Consisting of several distinctive towns and villages, The Berkshire region offers a plethora of unique cultural, historical, and recreational opportunities—making this lovely area an all-in-one vacation destination that shines throughout both the summer and winter seasons.

Venturing Out: Park 2 Park, Grand Junction: Bill’s Spill

Enjoying our content?

Subscribe and receive a weekly newsletter packed with awesome stories to inspire you!

Related articles

Blossoming Beauty: A Guide to Arkansas’ Botanical Gardens and Arboretums

There’s something magical about strolling through a botanical garden...

Scaling New Heights: 5 Epic Rock Climbing Spots in Iowa

Are you tired of the same old climbing routes?...

Adventures for Every Season in Pagosa Springs

From scenic drives in the fall and dog sledding...

A Weekend at the Banneker Hotel: Your Gateway to Washington, D.C.

If you’re seeking a weekend of history, culture and...

Hawaii Unleashed: The Ultimate Thrill-Seekers Guide to Paradise

With heart-pumping adventures on land, in the sea, and...