6 Best Small Towns to Explore on a Trip to The Berkshires

Berkshire Towns

Did you know the Berkshires have some of the most beautiful small towns in New England? Take a trip with us down the winding country roads as we tour this special part of Western Massachusetts. We’ll explore Lenox, Great Barrington, and more of the very best towns in the Berkshires.

New England Travel Inspiration

6 Best Towns in the Berkshires 

1. Great Barrington

Our first stop is easily one of the best Berkshire towns! Great Barrington is filled with a range of cafes and restaurants to suit any traveler’s style. Stroll along Main Street before turning onto Railroad Street which is full of unique shops. 

Also, be sure to check out the Monument Mountain hike. This trail has some of the most stunning views of Great Barrington, especially if you’re visiting in the fall season.

Grab a Coffee: Fuel Bistro, Marjoram, & Roux
Enjoy Lunch: Baba Louie’s Sourdough Pizza
Shop: Karen Allen Fiber Arts, Crystal Essence & Happy Place Berkshires
Stay: The Barrington or Fairfield Inn & Suites by Marriott

Berkshire Towns

2. Stockbridge

The historic town of Stockbridge is another popular place to visit in the Berkshires! It’s home to both great outdoor hiking trails and fascinating cultural activities.

Stop in at the Norman Rockwell Museum to experience where the famous artist lived and worked. After that, tour the Naumkeag Mansion and wander through the Berkshire Botanical Gardens. 

10 Fun Things to Do in Historic Stockbridge MA

Grab a Coffee: The Lost Lamb
Enjoy Lunch: Main Street Cafe
Shop: Seven Arts Gift Shop
Hike: Laura Lookout Tower & Ice Glen 
Stay: The Red Lion Inn & Stockbridge Country Inn

Berkshire Towns Stockbridge

3. Lee

Although Lee often flies under the radar compared to other towns in the Berkshires, there is plenty to do and see! Take in the beautiful main street and quaint New England architecture. If you’re a fan of shopping you can even check out the Lee Premium Outlets nearby.

Grab a Coffee: Prado’s Cafe
Enjoy Lunch: Starving Artist Creparie and Cafe
Shop: Lee Premium Outlets
Stay: Chambery Inn & Devonfield Inn

Best towns in The Berkshires

4. West Stockbridge 

West Stockbridge is a small Berkshire town that’s perfect to include in your itinerary. It’s located just seven minutes from historic Stockbridge and a 10-minute drive from Lenox.

There is a very small main street and some fun antique shops to check out. If you have time, be sure to stop at Olivia’s Overlook for an amazing view of the Stockbridge Bowl.

Grab a Coffee: Six Depot Roastery & Cafe
Enjoy Dinner: Truc Orient Express (Takeout) & Rouge
Shop: Shaker Mill Books & Charles H. Baldwin & Sons
Stay: Shaker Mill Inn

West Stockbridge

5. Williamstown

Williamstown is a hip and fun college town in the Berkshires that’s bursting with life! Besides the cafes and walking trails, another draw to the area is the famous Clark Art Institute. 

Also, be sure to check out the highest point in Massachusetts as Mount Greylock. The beautiful viewpoint is just a 30 minutes ride from Williamstown.

Grab a Coffee: Tunnel City Coffee
Enjoy Lunch: Tony’s Sombrero & Pappa Charlie’s Deli Sandwich
Shop: Where’d You Get That Inc.
Hike: Taconic Trail State Park
Stay: The Williams Inn & Maple Terrace Motel

Towns in the Berkshires

6. Lenox

No trip to the Berkshires is complete without spending an afternoon in Lenox. Honestly, this charming village is where we recommend travelers to base their adventures from!

Full of cute coffee shops and amazing hikes, there is no shortage of things to do in one of the best towns in the Berkshires. If possible, try and time your visit in the summer with a concert at Tanglewood. 

10 Things to do in Lenox MA: Tanglewood, Nature Walks, & More

Grab a Coffee: Shots Cafe
Enjoy Lunch: The Olde Heritage Tavern
Shop: Berkshire Classic & The Bookstore and Get Lit Wine Bar
Hike: Mass Audubon’s Pleasant Valley Wildlife Sanctuary
Stay: Gateways Inn & Courtyard by Marriott Lenox

The Berkshires Lenox Town

More of the Best Towns in the Berkshires

You should know there are endless Berkshire towns to discover in Western Massachusetts! After stopping in at some of our favorites, be sure to experience places like North Adams, Pittsfield, and Sheffield.

The small town vibes, history, and gorgeous walking trails are what keep us coming back time and time again. It’s also very convenient to rent a car in Boston and make the 2 hour drive to this special area of Massachusetts. 

Have any questions about this article or want to share more of the best Berkshire towns? Leave us a comment below! 

Safe Travels,
Brigitte & Jake

Stay in the Best Towns in the Berkshires

Ultra LuxuryMiraval Berkshires Resort & Spa – Take in some luxury in this historic Wyndhurst Mansion turned resort. Enjoy golfing, spa treatments, and views of the beautiful Berkshire countryside. 

Fun VacationCourtyard by Marriott Lenox – Just a quick drive from downtown Lenox, this is the perfect spot to relax after a fun day of exploring. While there are plenty of historic hotels and Airbnb’s in the area, we enjoyed having the modern amenities and swimming pool at the Courtyard by Marriot.

Bed & Breakfast Chambery Inn – This beautiful bed and breakfast is situated out in the countryside of Lee, but still close enough to walk to local restaurants and shops. You’ll also be just a few miles from attractions such a Tanglewood and Butternut Ski Resort.

Historic HotelRed Lion Inn – This historic hotel is a landmark in the town of Stockbridge which is one of the best Berkshires towns. Stroll through town which is right at your doorstep, or simply watch the day pass you by while sipping on drinks on the front porch.

For more places to stay in the Berkshires you can explore the latest prices here!

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Best Berkshire Towns

New England Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Scenic Boat Tour in Portland Maine! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

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  1. Lisa Alcombright
    October 4, 2023 / 10:56 pm

    What about Adams? Home of Mt. Greylock
    hike to the top many trails. Susan B. Anthony museum , Quaker House, Bike trails

    • Brigitte & Jake
      October 5, 2023 / 3:24 am

      Adams is great! So much history and nature to experience

  2. Margie Kierstead
    January 2, 2023 / 3:20 pm

    5 out of 6 of these towns are in Southern Berkshire County, where rich people from New York own secondary homes or weekend homes. They are definitely tourist towns.

    Williamstown has Williams College, where rich people send their students that don’t get into Ivy League schools.

    No wonder these towns are nice places to visit..

    • Brigitte & Jake
      January 2, 2023 / 7:28 pm

      What small towns would you suggest people visit in the Berkshires?

  3. August 2, 2022 / 9:57 am


    • Brigitte & Jake
      August 2, 2022 / 2:42 pm

      Another great town to visit!

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