Summer in the Berkshires: 7 must-visit mountain towns in Massachusetts

Aug 10, 2021

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

Update: Some offers mentioned below are no longer available. View the current offers here – Marriott Bonvoy Boundless Credit Card       

Planning your next vacation getaway on the East Coast? Tucked away in the Berkshires are six towns you should add to your summer bucket list. 

The Berkshires rest in the Taconic Mountains between New York and Boston. Home to some of the most picturesque hiking trails in the country, a vibrant art scene and historic landmarks, the towns are known for their intimate, yet lively New England charm. The great part about visiting the Berkshires is that you can find various activities in each town, and all either within walking distance or just a short drive away. Below are six must-visit towns to explore during the summer.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter.

In This Post

Where to go 

Lee 

October Mountain State Forest has some beautiful views of Mt. Greylock, the highest mountain in Massachusetts. (Photo by Mark Wilson/The Boston Globe/Getty Images)

Known for: “Gateway to the Berkshires,” down-to-earth charm, Lee Premium Outlets, lake boating

The “gateway to the Berkshires,” Lee has simultaneous down-to-earth charm and innovative culture. This town is great for shopping whether you’re searching for rare vintage items and antiques at the Retro Pop Shop or on the hunt for a bargain at Lee Premium Outlets where there are deals on famous fashion brands and a full food court. 

If you plan to visit during the weekend, don’t miss the Lee Farmer’s Market on Saturdays. For a unique art experience, Animagic is an appointment-only museum where you can learn about movie animation models by local artists, a great option with kids. 

If you crave outdoor time, head over to October Mountain State Forest for birding, hiking, mountain biking, kayaking or a picnic. There are plenty of noteworthy restaurants in town, too, from authentic Peruvian cuisine at Alpamayo restaurant to a romantic French bistro fare at Chez Nous.

Lenox

Lenox, Massachusetts. (Photo by Brian Bumby/Getty Images)

Known for: Tanglewood, Shakespeare & Company, The Mount (Edith Wharton’s literary home)

Lenox is conveniently located 10 minutes away from Lee and Stockbridge. It’s the setting of the famed Tanglewood music festival that runs from early June to mid-August, the summer home of the lauded Boston Symphony Orchestra. 

If you’re not a classical music fan, you may not have heard of this little town. However, although Lenox may look quiet and quaint, the international artists and talent that perform here every summer comprise an impressive collection of guests. In the summer of 2017, I spent six weeks in Lenox as part of Boston University Tanglewood Institute (BUTI) as a violinist in its Young Artists Orchestra. One memory that stands out was listening to John Williams conduct the Indiana Jones theme song and meeting the legend himself the next day at my rehearsal.

The town itself is rich with fascinating visitors and fun activities. Folks have claimed to have met Yo-Yo Ma while getting a classic American brunch at Haven Bakery or sat beside famous composers at outdoor concerts. While you are there, visit composer Aaron Copland’s memorial or explore novelist Edith Wharton’s (supposedly haunted) estate. 

A fun feature of the town is its scarecrow people, which can be seen “walking” down the street or sitting on a park bench. Lenox is just a two-hour drive from Boston and three hours from New York City, so it’s perfect for a weekend getaway for anyone in search of a place full of New England charm with an international flair

Stockbridge 

The Norman Rockwell Museum and studio in Stockbridge. (Photo by John Greim/LightRocket/Getty Images)

Known for: Norman Rockwell Museum, historic downtown, riverside hiking

Lenox’s neighbor, Stockbridge, is known for its historic downtown, outdoor hiking trails along the Housatonic River and former artistic residences such as the Norman Rockwell Museum. 

The Foundry in West Stockbridge is a new arts venue that puts together interesting programming, including everything from spoken word to chamber music. 

For some relaxing outdoor time head to the Berkshire Botanical Garden, one of New England’s oldest botanical gardens. Here you can stop and smell the flowers, take an art workshop or listen to Music Mondays.

North Adams & Williamstown

(Photo courtesy of the Williamstown Theatre Festival/Facebook)

Known for: Mass MoCA, Williams College, Williamstown Theatre Festival

North Adams and Williamstown are about a 30-minute drive from Pittsfield and about an hour north of the other towns. But don’t skip a visit to them. Williamstown is home to the Williamstown Theatre Festival, bringing in stars from Hollywood and Broadway. 

At the heart of Williamstown is Williams College, one of the top liberal arts schools in the country. You will also find the Massachusetts Museum of Contemporary Art (Mass MoCA), the largest contemporary museum in the country. 

Get a bite to eat at one of the many restaurants that support local farming, such as Mezze (which offers vegetarian, vegan and gluten-free options), The Public or The Break Room.

According to the locals, you can’t go wrong with any of the area’s hiking trails. Mount Greylock, in particular, has stunning views as the highest point in Massachusetts. 

Animal lovers should pay a visit to Colonial Alpacas, a small alpaca farm in Williamstown.

Great Barrington 

The view along Main Street in Great Barrington. (Photo by Barry Winiker/Getty Images)

Known for: outdoor activities, swimming holes, boutiques and galleries, fine dining

Centrally located in the Berkshires, Great Barrington’s proximity to the Appalachian Trail makes it a great summertime location for visiting the ski mountains, which become adventure parks in the summer (such as Catamount Adventure Park). You can also spend time outdoors at one of the many natural swimming holes or go horseback riding at Blue Riders Stables

Great Barrington is known for its fine dining. The Prairie Whale has a Pizza Garden Summer Pop-up along with their classic American fare, while Bizen Japanese Restaurant & Sushi Bar serves gourmet Japanese food from its robata charcoal grill. For a more laid-back, but still high-quality meal, check out Aroma Bar & Grill, a family-run Indian restaurant. 

The town also has a rich history: this was the town where slave Elizabeth Freeman (also known as Mumbet) sued for her freedom in 1781, eventually setting a state-recognized precedent to abolish slavery in Massachusetts.

Great Barrington was also the hometown of writer, activist and sociologist W.E.B. Du Bois, and the historic Du Bois Center is located just south of Main Street. Beyond the town hall is a monument citing the first pre-Revolutionary War resistance against the British. Other interesting historical facts about Great Barrington: Main Street was the first street in the United States to have electric lights, and Railroad Street is one of the oldest streets in the country. 

Pittsfield 

Pittsfield, Massachusetts. (Photo by DenisTangneyJr/Getty Images)

Known for: largest Berkshires city, cinemas and eclectic downtown attractions, First Fridays Artswalk, Berkshire Museum 

From its eclectic downtown and movie cinemas to the creative offerings of First Fridays Artswalk and the kid-friendly Berkshire Museum, Pittsfield is a must-see for the entire family. 

The Berkshire Museum offers half-day summer camps for kids grades one through six; sign them up for a unique learning experience, such as the CSI Monster Hunter or Animation programs. In the meantime, adults can check out the museum’s American landscape paintings. 

Catch a flick at the independently owned Beacon Cinema, and order a beer or glass of wine there while you’re at it. For a more active excursion, drive 12 miles north and challenge yourself to the Mountain Adventure Park.

Hungry? For traditionally-made fresh bread and pizza, visit Berkshire Mountain Bakery, featured in Netflix’s four-part documentary Cooked.  Also nearby is Brattle Farm to purchase fresh produce and pick herbs. 

How to get there 

There are several ways to get to the Berkshires, but make sure to plan ahead. The Berkshires have several airports accessible by jet or private plane, but it will cost you. The closest airport to the Berkshires is Albany International Airport (ALB), approximately 60 miles northwest of the area or Bradley International Airport (BDL) in Connecticut, about 70 miles from the Berkshires. Boston is the closest city, but Logan International Airport (BOS) is 135 miles away, a roughly a 2.5 hour car ride.

Whatever airport you choose, you will have to take a car, bus or train to enter the region. Below are several options. For more transportation information, visit the Berkshires official website.

  • By car: The Berkshires are accessible by car via interstate routes to Lee (also known as the “Gateway to the Berkshires”) from New York, New Jersey, Connecticut and Massachusetts. 
  • By bus: Peter Pan Bus Lines and Greyhound Lines travel to more than 30 locations in the Berkshires. Other bus lines that travel from metropolitan airports and train stations include Ally Charter Bus Boston, the National Charter Bus Boston and the Boston Charter Bus Company
    • One-way ticket from Albany, New York, to Lee, Massachusetts on Aug. 12, 2021:
      1. Peter Pan Bus Lines starts at $25
      2. Greyhound Lines starts at $15
  • By train: Amtrak has services to Pittsfield on the Lake Shore Limited 

Related: The best credit cards for commuting

Once you are in the Berkshires, you’ll do best to travel by car, especially when getting between towns. The Berkshires Regional Transit Authority (BRTA) operates buses with limited hours every day except on Sundays. Ridesharing services such as Uber and Lyft have become more popular in recent years, while taxis are harder to find.

Where to stay 

With plenty of outdoor activities, artistic attractions and historic landmarks in each town, and with each town about a 10-20 minute drive from one another (with the exception of North Adams and Williamstown, which are about 30-40 minutes north of the others), you can’t go wrong with what location you choose for your stay. 

From charming bed and breakfasts to luxury resorts, you can find a stay that will suit your needs. Many options are found in Lenox, such as the recently opened Miraval Berkshires Resort & Spa in Lenox.

Related: 15 things to know about staying at Hyatt’s brand-new Miraval Berkshires

You can also earn points at popular hotel brands such as:

  • Hilton Garden Inn between Lenox and Pittsfield, or the Hampton Inn in Lenox — If you book and stay at a Hilton hotel by Sept. 6, 2021, you can earn 2x bonus points on stays of one or two nights and 3x the bonus points on stays of three nights or more. Make sure you book directly via Hilton with a promo code for this 2x Points Package

Related: 16 best ways to earn more Hilton Honors points in 2021

  • Fairfield Inn & Suites by Marriott in Great Barrington — Use Chase’s Marriott Bonvoy Boundless Credit Card for three free night awards (each free night award has a redemption value of up to 50,000 bonus points, which is a value of up to 150,000 total points) after you spend $3,000 on purchases in the first three months from account opening. In addition, you can earn 10x total points on up to $2,500 within the first six months of account opening for combined purchases at restaurants, gas stations and grocery stores.

Related: Award traveler’s guide to Marriott Bonvoy

Related: The award traveler’s guide to IHG Rewards Club

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

Related: Complete guide to 2021 hotel promotions

For a stay that screams “the Berkshires” try any of these inns and hotels:

  • Yankee Inn in Lenox — A cozy but elevated stay with personal touches, such as their vintage posters in each room and cozy fireplaces. They are known for their Romantic Getaway Package. Take advantage of their current promotion when you book directly online and get 10% off your reservation.
  • Canyon Ranch in Lenox — Although versions of this wellness resort can be found in several other U.S destinations, their location at the historically rich Bellefontaine Mansion in Lenox makes this a truly unique, all-inclusive wellness experience. 
  • The Blantyre — A sumptuous luxury estate in Lenox known for its “gilded-age elegance” and locally sourced French cuisine at Café Boulud by the Michelin-starred Chef Daniel Boulud. This location is great for an adults-only vacation, though the estate welcomes children ages eight and up.
  • Red Lion Inn — In Stockbridge, the Red Lion comprises the charming Main Inn, the modern country Maple Glen and cozy villas. Each room is individually decorated with antiques and one-of-a-kind pieces to create a unique, luxurious experience. The Inn is pet-friendly too (you may even meet their feline friend Norman in the lobby).
  • Williams Inn — A new inn that channels the rustic elegance of the area’s farmhouses located in the heart of Williamstown with views of the Taconic Mountains. Among the inn’s top amenities is The Barn Kitchen and Bar, which offers full brunch, dinner and drinks menus with fresh ingredients from local farms.  

Bottom line

When visiting the Berkshires, go solo, take a couples’ vacation or visit with the family. Whether you prefer to lounge at one of the resorts or inns, listen to live entertainment, explore art museums or take on some of the many outdoor adventures, the Berkshires has something for everyone. The great part about visiting this region is that you can find a variety of activities in each town, all either within walking distance or just a short drive away. 

Featured photo by Dominic Defelice/EyeEm/Getty Images.

Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.

With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.

Apply Now
More Things to Know
  • Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights.
  • Fee Credit for Global Entry or TSA Pre✓®.
  • Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.
  • See Rates & Fees
Regular APR
15.74%-24.74% Variable
Annual Fee
$250
Balance Transfer Fee
N/A
Recommended Credit
Excellent/Good
Terms and restrictions apply. See rates & fees.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.