Summer in the Berkshires: 7 Essential Mountain Towns to Explore in Massachusetts

Are you planning your next East Coast getaway? Nestled in the Berkshires are six towns you won't want to miss this summer.

The Berkshires are located in the Taconic Mountains, situated between New York and Boston. Renowned for their stunning hiking trails, vibrant arts scene, and historic sites, these towns exude a charming New England vibe. One of the best things about visiting the Berkshires is the abundance of activities available in each town, all within walking distance or a quick drive. Here are six towns to discover this summer.

Where to Visit 

Lee

Highlights: The "Gateway to the Berkshires," charming atmosphere, Lee Premium Outlets, and opportunities for lake boating.

Known as the "gateway to the Berkshires," Lee blends rustic charm with a vibrant culture. It's an excellent destination for shopping, whether you're after unique vintage finds at the Retro Pop Shop or seeking great deals on popular brands at Lee Premium Outlets, complete with a diverse food court.

If you're visiting on the weekend, be sure to check out the Lee Farmer's Market on Saturdays. For a distinctive artistic experience, consider Animagic, a museum available by appointment, where you can explore local artists' movie animation models—a fantastic option for families.

For outdoor enthusiasts, October Mountain State Forest is perfect for birdwatching, hiking, mountain biking, kayaking, or enjoying a picnic. The town also boasts a variety of notable restaurants, from authentic Peruvian dishes at Alpamayo to romantic French cuisine at Chez Nous.

Lenox

Highlights: Tanglewood, Shakespeare & Company, The Mount (the literary home of Edith Wharton)

Lenox is just a 10-minute drive from Lee and Stockbridge. It hosts the renowned Tanglewood music festival, which takes place from early June to mid-August and serves as the summer residence of the celebrated Boston Symphony Orchestra.

If classical music isn't your thing, you might not be familiar with this charming town. Yet, despite its tranquil appearance, Lenox attracts a remarkable array of international artists and performers every summer. I had the pleasure of spending six weeks in Lenox during the summer of 2017 as part of the Boston University Tanglewood Institute (BUTI) as a violinist in the Young Artists Orchestra. One unforgettable moment was hearing John Williams conduct the Indiana Jones theme, followed by the incredible experience of meeting him the next day at my rehearsal.

The town is brimming with intriguing visitors and enjoyable activities. Many have claimed to have encountered Yo-Yo Ma while savoring a classic American brunch at Haven Bakery or found themselves next to renowned composers at outdoor concerts. While you're there, be sure to visit the memorial for composer Aaron Copland or explore the (reportedly haunted) estate of novelist Edith Wharton.

One quirky attraction in town is its scarecrow figures, which can be spotted "walking" down the street or lounging on park benches. Lenox is conveniently located just two hours from Boston and three hours from New York City, making it an ideal weekend retreat for those seeking New England charm with an international twist.

Stockbridge

Highlights: The Norman Rockwell Museum, charming historic downtown, and scenic riverside hiking.

Lenox's neighbor, Stockbridge, is celebrated for its historic downtown, scenic hiking trails along the Housatonic River, and iconic artistic sites like the Norman Rockwell Museum.

The Foundry in West Stockbridge serves as a vibrant new arts venue that hosts a diverse range of programming, from spoken word performances to chamber music concerts.

For a peaceful outdoor experience, visit the Berkshire Botanical Garden, one of the oldest botanical gardens in New England. Here, you can enjoy the beauty of the flowers, participate in an art workshop, or attend Music Mondays.

North Adams & Williamstown

Highlights: Mass MoCA, Williams College, Williamstown Theatre Festival

North Adams and Williamstown are approximately a 30-minute drive from Pittsfield and about an hour north of the surrounding towns. However, a visit here is a must. Williamstown hosts the Williamstown Theatre Festival, attracting stars from both Hollywood and Broadway.

At the center of Williamstown lies Williams College, one of the premier liberal arts institutions in the nation. You can also explore the Massachusetts Museum of Contemporary Art (Mass MoCA), the largest contemporary art museum in the U.S.

Dine at one of the numerous restaurants that prioritize local farming, such as Mezze (offering vegetarian, vegan, and gluten-free dishes), The Public, or The Break Room.

Locals agree that you can't go wrong with any of the area's hiking trails. Mount Greylock, in particular, offers breathtaking views as the highest peak in Massachusetts.

Animal enthusiasts should stop by Colonial Alpacas, a charming alpaca farm located in Williamstown.

Great Barrington

Highlights: outdoor recreation, swimming spots, unique boutiques and galleries, fine dining options

Nestled in the heart of the Berkshires, Great Barrington's close proximity to the Appalachian Trail makes it an ideal summer destination. The nearby ski mountains transform into adventure parks during the warmer months, like Catamount Adventure Park. You can also enjoy the outdoors at various natural swimming holes or go horseback riding at Blue Riders Stables.

Great Barrington is renowned for its fine dining scene. The Prairie Whale features a Pizza Garden Summer Pop-up alongside its classic American dishes, while Bizen Japanese Restaurant & Sushi Bar offers exquisite Japanese cuisine cooked over a robata charcoal grill. For a more casual yet quality meal, visit Aroma Bar & Grill, a family-operated Indian restaurant.

The town boasts a rich history: it was here that Elizabeth Freeman, also known as Mumbet, sued for her freedom in 1781, establishing a state-recognized precedent that led to the abolition of slavery in Massachusetts.

Great Barrington is also the birthplace of writer, activist, and sociologist W.E.B. Du Bois, with the historic Du Bois Center located just south of Main Street. Beyond the town hall, you can find a monument commemorating the first pre-Revolutionary War resistance against British rule. Notable historical facts include that Main Street was the first street in the U.S. to have electric lights, and Railroad Street ranks among the oldest streets in the nation.

Pittsfield

Highlights: largest city in the Berkshires, cinemas and diverse downtown attractions, First Fridays Artswalk, Berkshire Museum

Pittsfield is a must-visit destination for families, offering an eclectic downtown, movie theaters, the creative events of First Fridays Artswalk, and the kid-friendly Berkshire Museum.

The Berkshire Museum provides half-day summer camps for children in grades one through six, offering unique learning experiences like the CSI Monster Hunter and Animation programs. Meanwhile, adults can explore the museum's collection of American landscape paintings.

Catch a movie at the independently-owned Beacon Cinema, where you can enjoy a beer or glass of wine while watching. For a more adventurous outing, drive 12 miles north to take on the challenges at Mountain Adventure Park.

Feeling hungry? For freshly made traditional bread and pizza, head to Berkshire Mountain Bakery, featured in Netflix's four-part documentary Cooked. Nearby, you can also visit Brattle Farm for fresh produce and herb picking.

How to reach the Berkshires 

There are various routes to the Berkshires, so be sure to plan ahead. Several airports accommodate jets and private planes, but be prepared for the cost. The nearest airport is Albany International Airport (ALB), located about 60 miles northwest, followed by Bradley International Airport (BDL) in Connecticut, approximately 70 miles away. While Boston is the closest major city, Logan International Airport (BOS) is 135 miles from the Berkshires, roughly a 2.5-hour drive.

Whichever airport you select, you'll need to travel by car, bus, or train to reach the region. Below are several options. For further transportation details, visit the Berkshires official website.

• By car: You can access the Berkshires by interstate routes leading to Lee, known as the "Gateway to the Berkshires," from New York, New Jersey, Connecticut, and Massachusetts.
• By bus: Peter Pan Bus Lines and Greyhound Lines serve over 30 locations in the Berkshires. Additional bus services connecting from metropolitan airports and train stations include Ally Charter Bus Boston, National Charter Bus Boston, and Boston Charter Bus Company.
• One-way fare from Albany, New York, to Lee, Massachusetts on August 12, 2021:

1. Peter Pan Bus Lines fares start at $25
2. Greyhound Lines fares start at $15

• By train: Amtrak offers service to Pittsfield via the Lake Shore Limited

Once you're in the Berkshires, traveling by car is the most convenient option, especially for getting between towns. The Berkshires Regional Transit Authority (BRTA) operates buses with limited hours daily, except Sundays. Ridesharing services like Uber and Lyft have gained popularity recently, although taxis are less common.

Where to stay 

With an abundance of outdoor activities, artistic attractions, and historic sites in each town, and with towns being only a 10-20 minute drive apart (except for North Adams and Williamstown, which are about 30-40 minutes north), you'll find great options no matter where you choose to stay.

From cozy bed and breakfasts to luxurious resorts, you'll discover accommodations to fit your needs. Many options are available in Lenox, including the newly opened Miraval Berkshires Resort & Spa in Lenox.

You can also accumulate points with popular hotel brands such as:

• Hilton Garden Inn located between Lenox and Pittsfield, or the Hampton Inn in Lenox -- If you reserve and stay at a Hilton hotel by September 6, 2021, you can earn 2x bonus points on one or two-night stays and 3x bonus points on stays of three nights or more. Be sure to book directly through Hilton using the promo code for the 2x Points Package.

• Fairfield Inn & Suites by Marriott in Great Barrington -- Utilize Chase's Marriott Bonvoy Boundless Credit Card to earn three free night awards (each valued up to 50,000 bonus points, totaling up to 150,000 points) after spending $3,000 within the first three months of account opening. Additionally, earn 10x total points on combined purchases at restaurants, gas stations, and grocery stores up to $2,500 during the first six months.

• Holiday Inn in South Lee -- Most IHG brands offer 10x points, and using your IHG One Rewards Premier Credit Card will earn you 5x points on travel, gas stations, and restaurants, along with 3x points on other purchases. Furthermore, the IHG Premier Credit Card currently provides a sign-up bonus of 140,000 bonus points after spending $3,000 within the first three months. Additionally, earn up to $100 in statement credits on purchases at IHG properties within the first year.

• Wyndhurst Manor & Club in Lenox, Massachusetts -- Book a stay with the Hyatt Night In package by September 12, 2021, and enjoy VIP perks for staycations or weekend getaways, including extended check-in/check-out times, discounts on amenities and extra rooms, plus upgrades based on availability. Use the special offer code NIGHTIN.

For a quintessential Berkshires experience, consider staying at any of these charming inns and hotels:

• Yankee Inn in Lenox -- A cozy yet refined escape, featuring vintage posters in each room and inviting fireplaces. They offer a Romantic Getaway Package and currently provide a 10% discount on direct online bookings.
• Canyon Ranch in Lenox -- While wellness resorts can be found in various U.S. locations, the one situated in the historic Bellefontaine Mansion in Lenox offers a truly distinctive all-inclusive wellness retreat.
• The Blantyre -- An opulent luxury estate in Lenox celebrated for its "gilded-age elegance" and locally sourced French cuisine at Café Boulud, crafted by Michelin-starred Chef Daniel Boulud. Ideal for an adults-only getaway, although the estate welcomes children aged eight and older.
• Red Lion Inn -- Located in Stockbridge, the Red Lion features the quaint Main Inn, the contemporary Maple Glen, and charming villas. Each room is uniquely adorned with antiques and distinctive pieces, providing a luxurious and personalized experience. The Inn is also pet-friendly, so you might meet their resident feline, Norman, in the lobby.
• Williams Inn -- A newly established inn that embodies the rustic charm of local farmhouses, situated in the heart of Williamstown with scenic views of the Taconic Mountains. The Barn Kitchen and Bar is among the inn's top amenities, offering a full menu of brunch, dinner, and drinks made from fresh local ingredients.

Final thoughts

When exploring the Berkshires, whether you're solo, on a couples' retreat, or with family, there's something for everyone. Enjoy lounging at resorts or inns, experiencing live entertainment, visiting art museums, or engaging in various outdoor adventures. The beauty of this region lies in its diverse activities available in each town, all within walking distance or a short drive from one another.