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

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.

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New England Travel Inspiration

• Planning a Visit to the Berkshires: 10 Step Fun & Easy Travel Guide
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• Bash Bish Falls: Easy Hike to the Tallest Waterfall in MA
• 9 Delicious Fall Desserts and Drinks to Enjoy in New England
• Hancock Shaker Village: Fun Day of History and Nature in the Berkshires

6 Best Towns in the Berkshires 

1. Great Barrington

Our first stop is easily one of the best Berkshires 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 in this funky Berkshire town.

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

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 unique 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 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

3. Lee

Although Lee often flies under the radar compared to the other best 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 Creperie and Cafe
Shop: Lee Premium Outlets
Stay: Chambery Inn & Devonfield Inn

4. West Stockbridge 

West Stockbridge is a small Berkshire town that’s perfect to include as part of your day of exploring. 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 unique shops to check out. Pop into Shaker Mill Books to pick up some vacation reading before strolling through TurnPark Art Space. 

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

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. You can also check out the highest point in Massachusetts as Mount Greylock is just a 30 minute ride away.

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

6. Lenox

No trip to the Berkshires is complete without spending at least the afternoon in the charming village of Lenox. Honestly, this is where we would 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

What do you think are the best towns in the Berkshires? Let us know what your favorite Berkshire towns are in the comments below! 

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar! 

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Stay in the Best Towns in the Berkshires

Ultra Luxury – Miraval 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 Vacation – Courtyard 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 Hotel – Red 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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USA 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 Sea Cave Kayak Tour in La Jolla California! 

 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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