Everything you need to know about a trip to the Berkshires

Situated in western Massachusetts just a few hours from big-city hubs like Boston and New York, the Berkshires are one of the best-loved outdoor playgrounds in the Northeast and a perfect getaway for all ages.

Unlike some of the region’s other favorite summertime getaways like Cape Cod and the Jersey Shore, the Berkshires are all about solitude. Crowds are relatively sparse, allowing visitors to indulge in some R&R as they reconnect with nature. The Berkshires are filled with pretty lakes, rustic New England towns, endless scenic roads, and tons of cultural and culinary offerings. 

No matter what time of year you are visiting the Berkshires, you can expect an array of fun activities at your disposal. Below you’ll find some of the best things to do in the Berkshires, from hiking and swimming to skiing and leaf-peeping. 

Where are the Berkshires Located?

So, where are the Berkshires, exactly? This region stretches across the entire western part of Massachusetts, with Vermont to the north, New York to the West, and Connecticut to the South. 

What’s the best way to get to the Berkshires?

Those traveling from major cities like Boston and New York City can access the Berkshires in less than three hours by car. Depending on your final destination, the trip takes around two hours from Boston and about two and a half hours from NYC. 

The Berkshires can also be reached via train. The easiest way to get to the Berkshires from New York City is taking a 2-hour Amtrak train from New York Penn Station to Hudson, NY (which is a very charming town with tons to do). From Hudson, the Berkshires is about a 45-minute drive depending on your final destination. Additionally, Amtrak recently announced a new seasonal weekend service from New York City to Pittsfield, just in time for the summer season.

From Boston, you can hop on Amtrak’s daily service toward Chicago on the Lake Shore Limited and hop off in Pittsfield. 

If you’re flying to the Berkshires, the closest airport is Bradley (BDL) near Hartford, Connecticut. From Bradley, the Berkshires are about a one-hour drive. 

When considering where to stay in the Berkshires, remember that the towns are never too far apart from one another. And anyways, the scenic drive between attractions is often half the fun!

The Best Towns and Villages to Visit in the Berkshires

There are tons of charming towns in the Berkshires to discover, but there are few that deserve a spot on every traveler’s bucket list. Below you’ll find a few of our favorites in the Berkshires. 

New Marlborough

We’re a bit biased, but tucked near the Connecticut border in southern Massachusetts, New Marlborough is one of the best villages in the Berkshires. It has all the quintessential attributes of the region, including historic landmarks, great restaurants, and tons of outdoor activities for all four seasons. 

During the summer you can cool off in the nearby Lake Buel or York Lake, and in the winter, the ski slopes of Ski Butternut are just a few minutes away. 

Once you work up an appetite there is an abundance of great restaurants in New Marlborough. Fresh farm-to-table cuisine is served up on ever-changing menus across town, including favorites like Cantina 229, The Old Inn on the Green, and Gedney Farm. In addition to delicious food, these venues have beautiful grounds you can explore and some even have lodging options. If you’re looking for a delicious pastry or to enjoy local favorite No. 6 Depot Coffee, head straight to the Southfield Store, our favorite place to grab breakfast or lunch before a hike. 

Great Barrington

Great Barrington is the gateway to the Berkshires South County. The cozy cafes, award-winning restaurants, unique shops, and a postcard-perfect downtown all make Great Barrington a great place to visit. 

Start your day with a coffee from Majoram & Roux or Fuel Bistro, then head down to the River Walk to enjoy some great views of the Housatonic River. Once you get hungry, there’s a full line-up of highly-rated restaurants in Great Barrington, including The Prairie Whale, Twoflower cafe, Baba Louie’s Sourdough Pizza Co, and the Marketplace. For cocktails, don’t miss Mooncloud, spinning up delicious craft cocktails in a cozy bar. And for dessert, head to the SoCo Creamery for a scoop of micro-batched hand-crafted ice cream, including many vegan options.

While downtown Great Barrington is a fun place to spend some time, its proximity to the great outdoors is what really makes Great Barrington one of the best towns in the Berkshires. It sits near some of our favorite hikes in the Berkshires, including Monument Mountain, Lake Mansfield, the Housatonic River, and a section of the Appalachian Trail.

Lenox

You can’t visit the Berkshires without spending a little time in Lenox. Lenox is everything a typical New England village should be. It has great restaurants, a beautiful downtown area, cute coffee shops, and tons of outdoor offerings bordering the town. 

It’s easy to indulge your senses during your time in Lenox, whether it be with an open-air concert at Tanglewood, a spa day at Canyon Ranch, or a white tablecloth meal at Bistro Zinc. 

Lenox is great for literary lovers as well, and this is where you’ll find The Mount – the home of the late American novelist Edith Wharton. Some of her most famous work was created in this house, and today you can tour the historic home and grounds that pay homage to her life.   

Stockbridge

Home to the famous Norman Rockwell Museum and the historic Naumkeag Mansion, Stockbridge is another one of the best towns in the Berkshires.

In addition to the collection of cultural offerings in historic Stockbridge, there are also plenty of outdoor activities. You can stroll through the stunning Berkshire Botanical Gardens, take a hike at Goodrich Memorial Park, or kayak around Lake Mahkeenac. You could also reconnect with nature while reconnecting with yourself at Kripalu – a center for yoga and health that offers a variety of seasonal programs with an emphasis on body, mind, and spirit. 

After a busy day of exploring, there’s no better place for dinner and a drink than the Red Lion Inn. Operating since 1773, the tavern is as historic as it is iconic. Enjoy a cold drink on the porch, or dine on modern interpretations of authentic New England cuisine in the antique dining room. 

Honorable Mentions

The Berkshires are filled with ample quaint towns. We’ve already named a few of our personal favorites but for those staying a few extra days in the Berkshires here are a few honorable mentions.

The small town of Becket (situated just outside of Pittsfield) is home to Jacob’s Pillow – a National Historic Landmark and renowned dance training center. Jacob’s Pillow hosts the nation’s longest-running dance festival, which is held every summer from mid-June through late August.

The acclaimed MASS MoCA (Massachusetts Museum of Contemporary Art) is housed in a converted factory complex in North Adams, located in the northwest corner of the state. This massive museum boasts one of the country’s largest collections of contemporary visual art, so be sure to carve out plenty of time to explore all 250,000 square feet of gallery space. 

Step back in time at the Hancock Shaker Village, located on the outskirts of Pittsfield. This living history museum dates back to the late 1700s and gives visitors a look into Shaker life, including a working farm, a history museum, and thousands of artifacts. 

Theater lovers should make a beeline to Williamstown for the annual Williamstown Theater Festival. This iconic event takes place each summer on the campus of Williams College and presents plays, readings, workshops and more.

Rain or shine, during the summer you’ll find an abundance of farmers markets around various villages. Some of the best include the Berkshire Area Farmers Market in Lanesborough, the Hancock Farmers Market in Hancock, and the Otis Farmers Market in East Otis.  

Best Outdoor Activities in the Berkshires

Best Hikes in the Berkshires

Getting out in nature is one of the best things to do in the Berkshires. There are dozens of great hiking trails in this area. So whether you’re a beginner looking for a leisurely stroll or a seasoned pro seeking out the best views, you’ll find plenty of options. Monument Mountain and Mount Greylock are two of the most popular places for hiking in the Berkshires. 

Monument Mountain

Situated a few minutes from the center of Great Barrington, Monument Mountain is one of the most popular places to hike while visiting the Berkshires. Standing tall at 1,642 feet, the summit offers panoramic views of the Housatonic River Valley below. If you don’t feel like trekking all the way to the top, there are plenty of shorter trails around the mountain as well. 

Mount Greylock

Just shy of 3,500 feet, Mount Greylock boasts the tallest peak in the state. On a clear day, hikers will be able to see five different states from the summit, including Massachusetts, New York, New Hampshire, Connecticut, and Vermont. The mountain is located within a state reserve, so there are plenty of other hiking trails if you don’t feel like going all the way up to the summit.

Other Outdoor Activities in the Berkshires

In addition to hiking, there are tons of fun ways to get out and explore the great outdoors while visiting the Berkshires. 

Water Sports

During the summer, the pretty lakes around the region are hubs for swimming, kayaking, and fishing. 

One of the most scenic lakes of the bunch is the 511-acre Pontoosuc Lake, especially when the fall colors are in full bloom. You can rent a pontoon from the Berkshire U-Drive Boat Rental tucked right on the lake shores, or bring your own boat along and utilize the public boat ramp located on the water’s south end. 

Onota Lake is another popular pick, thanks to its sandy shoreline. In addition to the beach, visitors can also enjoy the walking path, fishing pier, and excellent mountain views. The lake is a popular hub for fishing, water skiing, and sailing. You can rent kayaks, canoes, pedal boats, and more from the Onota Boat Livery, or launch your own boat from the public Onota Lake boat launch on the east shore. 

Great Barrington’s Lake Mansfield is a great place for a beach day, especially if you’re visiting the Berkshires with the kids in tow. Lifeguards patrol the sandy beach, and there’s also a swing set and playground located nearby. Other amenities of Lake Mansfield include a wooded walking trail, picnic tables and grills, and bathrooms. 

Adventure Parks

The Berkshires also have some fun adventure parks with canopy trails, zip lines, and other exhilarating elements to challenge visitors both young and young at heart. Two of the most popular adventure parks in the area are the Catamount Aerial Adventure Park in South Egremont and the Ramblewild Adventure Park in Lanesborough.

Winter Sports

Visitors to the Berkshires will find many activities to keep them busy throughout the winter months. The mountainous terrain makes the region a haven for winter sports enthusiasts, and there’s no better spot in the Northeast to take to the slopes than the Berkshires. 

Jiminy Peak is the biggest resort in the area, but there are plenty of options for skiing and snowboarding in the Berkshires, including Ski Butternut, Catamount, and Bousquet Mountain, among others. If you’re searching for the most affordable lift passes, you may want to opt for the ‘Best Deal in the East’ at Butternut. During the week, lift tickets are just $35 dollars.

Snowshoeing and cross-country skiing are also great winter pastimes in the Berkshires, and you’ll find miles of scenic trails across the region. Whether you’re new to the sport or a seasoned pro, you’ll want to check out the groomed trails at Stump Sprouts, located in Hawley. There are over 15 miles of scenic trails to traverse here, along with gear rentals and a charming warming room in a New England Farm House. Other great cross-country skiing and snowshoeing spots include Notchview in Windsor and Canterbury Farms in Becket. 

Cultural Offerings in the Berkshires

Come for the outdoor offerings, but stay for the cultural attractions. The Berkshires are brimming with exciting museums, iconic entertainment venues, historic landmarks, and tantalizing food and drink options. So, whether you want to check out one of the famous art museums, catch some live music or a dance performance, visit one of the historic homes, or simply indulge in fresh farm-to-table cuisine, your options are truly endless.  

Live Entertainment

If you want to see some live music while visiting the Berkshires, don’t miss Tanglewood – a beautiful outdoor music venue known to host stellar performances. People have been rocking out to all kinds of music at Tanglewood since the 1930s, and currently, the Boston Symphony Orchestra plays regular shows in the summer. Other additions to the annual lineup have included stars such as James Taylor, Earth, Wind & Fire, Van Morrison, and Ringo Starr and his All-Starr Band, to name just a few!

Jacob’s Pillow also has a great cast of performances for their annual summer dance festival. Acts vary from performances by the New Orleans Jazz Orchestra and Miami City Ballet to evocative choreography from the Ladies of Hip Hop Dance Collective and Indigenous Enterprise, among many others. Classes and workshops are also available throughout the summer, along with “PillowTalks,” exhibitions, and freestyle dance parties. 

Museums

There are many fantastic museums scattered around the Berkshires. Whether you’re interested in art, history, or literature, you’ll find numerous options to indulge in your favorite topics around the region. 

Often considered the absolute best museum in the region, the Clark Art Museum in Williamstown is a must-see. You could also check out the world’s largest collection of Rockwell’s work at the Norman Rockwell Museum in Stockbridge or explore the contemporary exhibitions at the Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams. 

Historic homes abound in the Berkshires. From the Naumkeag Mansion and the Ventfort Hall Mansion to The Mount (Edith Wharton’s home) and the Herman Melville Arrowhead Museum, you’ll have plenty of chances to step back in time and learnall about the Berkshires’ fascinating history. 

Food and Drink

One of the best parts about visiting the Berkshires is the food. The area is rich in fields and farms, which gives way to menus full of fresh, local ingredients and some of the best farm-to-table cooking in the country.

While the list is non-exhaustive, some of the tastiest meals in the Berkshires are served up at the Old Inn on the Green in New Marlborough, Cantina 229 right nearby in New Marlborough, and the Prairie Whale in Great Barrington. The Berkshires also have plenty of places to stop off for a drink. If you’re looking for pizza that rivals anything you’ll have in New York or any other city be sure to stop by Roberto’s in Sheffield. 

Some of our favorite cocktails can be found at Mooncloud right in the heart of Great Barrington. Craft beer aficionados will appreciate the abundance of breweries in the region, including Berkshire Brewing Company and Big Elm Brewing, among many others. Wine lovers should aim for a pit stop at Balderdash Cellars, and hard cider enthusiasts can indulge at the Berkshire Cider Project.

Best Time to Visit the Berkshires

There’s truly no bad time to visit the Berkshires. Each season has its own magic, which means visiting the Berkshires is possible year-round.

While many visitors flock to the area in the summer to swim in the pretty lakes and enjoy the good weather, autumn is perhaps the best time to visit the Berkshires. Fall foliage is at its peak, making all the popular outdoor activities even more scenic. Winter is also a great time for visiting the Berkshires thanks to the numerous ski resorts that dot the area. An extra added bonus in winter if the place you’re staying, like Oak Hill House, has a hot tub or fire pit to keep you cozy during those snowy winter nights.