9 Best Towns in the Berkshires and What to Do There

If it's your first time visiting the Berkshires and you're wondering the best towns to visit and what to do in each town then you're in luck! This guide covers everything you need to know if you're visiting the Berkshires especially if it's the first time. 💗

Since Berkshire County is pretty spread out - 50 miles north to south on the western side of Massachusetts, this guide highlights the best part of each area and town in the Berkshires. Find the pros and cons of each region of the Berkshires. Looking to hike? Find the towns with the best trails. Want to fill your time with museums and shows? Find the the best towns to do so!

This guide to visiting the Berkshires tells you the best areas and towns to stay in depending on the getaway you want and the activities you want what to do! You'll also find the best places to eat and visit in each town.

I was lucky enough to have spent several years living and working in the Berkshires in Lenox and Great Barrington. I slowly got to know all the towns and each weekend would explore more and more. I found my favorite spots and places that are widely agreed upon favorites including the best chocolate shop ever, where to find the BEST croissants, the best hikes in the Berkshires, walks, waterfalls, farms, museums!

Now, living next door in Connecticut, I still come back often; several times a month for a day or weekend trip in the Berkshires to get my fix of this beautiful area.

So come along and read all about what makes these Berkshire towns special and find out which area you should visit!

I know you’ll find this guide to visiting the Berkshires (from someone who’s lived here) very helpful as you plan your trip! Let’s get to it and explore the best of the Berkshires!

🗺️ Visiting the Berkshires: 9 Towns to Visit

🌄Southern Berkshires

The southern part of the Berkshires is often the most popular with visitors. Towns here include Sheffield, Egremont, Great Barrington, and Stockbridge.

The southern Berkshires is a personal favorite for me and not just because I'm coming from CT! A mountainous region of the Appalachian Trail runs through the southern towns here which makes for a beautiful backdrop as you drive as well as hikes with the best views. The southern towns combine to make a great area for adventure, amazing places to eat, and historical sites!

Best things to do in the Southern Berkshires:

• Berkshire Botanical Garden
• Norman Rockwell Museum
• Chesterwood – Historic studio of sculptor Daniel Chester French.
• Small-town shopping and antiques along the quaint Main Streets of Stockbridge or Great Barrington.
• Hike Flag Rock at Monument Mountain Reservation or (more challenging) Mount Race & Race Brook Falls
• Hike to Bash Bish Falls (tallest waterfall in MA!)
• Visit Taft Farms for seasonal produce, the best apple cider donuts, and prepared foods
• Scenic drives along Route 7 or back roads of Sheffield and Egremont
• The Patisserie in Great Barrington for THE BEST baked goods
• Prairie Whale for meals using local produce & meat

🗺️ Best towns to visit in the Southern Berkshires:

Great Barrington

There's so much to do in Great Barrington and it's one of my personal favorites—and not just because I used to live here. It’s lively, walkable, and full of shops, restaurants, and bakeries (I promise, the croissants alone are worth it!). Monument Mountain towers above town and offers a classic Berkshires hike with sweeping views. Ski Butternut is has lots of family-friendly activities if you're visiting the Berkshires in winter!

➡️ Stay in Great Barrington for an array of food choices, a vibrant downtown, and easy access to hikes and outdoor activities.

🛏️ Where to stay in Great Barrington: The Granville House 🏡 🌟 9.8 'Exceptional' on Booking.com (dog-friendly)

Stockbridge

Stockbridge feels straight out of a Norman Rockwell painting—literally, since his museum is located here and the quaint downtown was an inspiration for many paintings. The town is also home to Chesterwood (the studio of Lincoln Memorial sculptor Daniel Chester French) and the Berkshire Botanical Garden.

➡️ Stay in Stockbridge for a classic small-town feel and easy access to cultural sites.

🛏️ Where to stay in Stockbridge: The Red Lion Inn 🦁🌟 8.2 'Very Good' on Booking.com (dog-friendly)

Egremont & Sheffield

These towns are smaller and quieter, perfect for those looking to escape the crowds and get off the beaten path of the more popular Berkshire destinations. Think less downtown strolling and more mountains and trails. Egremont is home to some of the best big mountain hikes in the Berkshires including Mount Race, Alander Mountain, and the tallest waterfall in MA, Bash Bish Falls.

I love the drive alone though Egremont and Sheffield as they're dotted with antique shops, inns, farms, and country back roads that make for the most scenic drives.

➡️ Stay in Egremont for proximity to the Appalachian Trail, a quieter country getaway, a mix of old charm and outdoor beauty.

🛏️ Where to stay in Egremont: Wilder House Berkshires 🌟 9.6 'Exceptional' on Booking.com

🎶Central Berkshires

The heart of the Berkshires includes Lenox, Lee, Pittsfield, and Richmond. This is where arts and culture meet rolling hills and country roads. If you're into hiking you'll find lots of moderate hikes and scenic strolls in this area of the Berkshires but the bigger mountain views that you'll find in the southern section and northern section of the Berkshires.

Central Berkshires is the best choice for you if you want to have the option to drive north or south and want a great sampling of what the Berkshires has to offer. It is also the best if you're looking for higher end stays, spa destinations, and retreats although you'll find a mix of inns and more affordable stays here too.

Best things to do in the Central Berkshires:

• Catch a concert at Tanglewood: Summer home of the Boston Symphony Orchestra; concerts, lawn events.
• Visit The Mount (Edith Wharton's estate) & stroll the gardens (🐶 friendly)
• Visit Naumkeag: 48-acre public garden & historical home with seasonal events
• Shakespeare & Company: Live performances in a stunning old theater.
• Visit Hancock Shacker Village (not dog friendly, lots of family friendly seasonal activities)
• Berkshire Museum: mix of art, history, and natural science
• Hike Kennedy Park (rolling trails) or Pleasant Valley Audibon Sanctuary
• Walk the quaint downtowns of Lenox and Lee
• Chocolate Springs Cafe for THE BEST chocolates ever!!
• Haven Café & Bakery – Lenox favorite for brunch and baked goods.
• Lee Premium Outlets – Shopping for visitors who want a break from hiking or museums.

🗺️ Best towns to visit in the Central Berkshires:

Lenox

Lenox is one of the most popular bases in the Berkshires, known for its upscale inns, boutique shops, and cultural landmarks. In the summer, Tanglewood (the summer home of the Boston Symphony Orchestra) draws thousands of music lovers as people fight for tickets to James Taylor and Yo-Yo Ma but don't worry because the Boston Symphony Orchestra plays here weekly in the summer and there are lots of lawn seats available! Other highlights include The Mount, Shakespeare & Company, and Canyon Ranch Spa.

➡️ Stay in Lenox for a central Berkshire location, a luxury stay, cultural trip, or a romantic getaway.

🛏️ Where to stay in Lenox: The Cornell Inn 🌟 9.0 'Wonderful' on Booking.com

Lee

Often considered the “gateway to the Berkshires,” Lee is right off the Mass Pike, making it easy to reach. It’s more affordable than Lenox and a convenient spot for exploring the southern and central parts of the region. It also has a charming downtown and outlets nearby.

➡️ Stay in Lee for a budget-friendly trip, central access, and family-friendly feel.

🛏️ Where to stay in Lee: Chamberay Inn 🌟 8.4 'Very Good'

Pittsfield

Pittsfield is the largest city in the Berkshires, so it has more restaurants, shops, and services. It’s also home to the Berkshire Museum, Barrington Stage Company, and easy access to nearby lakes and trails. If you want a central location with more nightlife and activity, Pittsfield is a solid choice.

➡️ Stay in Pittsfield for more of a nightlife scene, trendy dining options, and a city base.

🛏️ Where to stay in Pittsfield: Hotel on North 🌟 9.0 'Wonderful'

🖼️Northern Berkshires

The northern region includes Lanesborough, Cheshire, Adams, North Adams, and Williamstown. This area combines rugged mountain scenery with world-renowned art museums.

Best things to do in the Northern Berkshires:

• Mount Greylock State Reservation – Hike or drive to Massachusetts' tallest summit, climb the Veterans War Memorial Tower.
• Hoosac Range trails – Hiking and scenic views near Adams and North Adams.
• MASS MoCA (North Adams) – World-class contemporary art museum.
• Clark Art Institute (Williamstown) – Art museum with beautiful grounds.
• Williams College Museum of Art – Smaller but excellent collection.
• Williamstown Theatre Festival – Summer performances at the college theater
• Local cafés and bakeries in North Adams and Williamstown.
• Breweries and cideries scattered in the northern Berkshires.
• Ski Jiminy peak

🗺️ Best towns to visit in the Northern Berkshires:

North Adams

A former mill town turned arts hub, North Adams is home to MASS MoCA, one of the largest contemporary art museums in the country. The town also has a growing food scene and easy access to outdoor adventures.

➡️ Stay in North Adams if you're a contemporary art lover, creative traveler, and want a down-to-earth town close to Mount Greylock.

🛏️ Where to stay in North Adams: The Porches Inn at Mass MoCA 🌟 8.7 'Excellent' 🐶 Dog-friendly

Williamstown

Just north of North Adams, Williamstown is a classic college town (home to Williams College) with a lively cultural scene. Don’t miss the Clark Art Institute and Williamstown Theatre Festival in summer. It’s also one of the prettiest small towns in Massachusetts.

➡️ Stay in Williamstown for art and theatre enthusiasts, college-town charm, and scenic beauty.

🛏️ Where to stay in Williamstown: The Williams Inn 🌟 9.4 'Wonderful' 🐶 Dog-friendly

Adams, Cheshire & Lanesborough

These smaller towns are great for outdoor adventures. Adams is a gateway to Mount Greylock, the tallest mountain in Massachusetts. You can hike or drive to the summit for incredible views and the historic Veterans War Memorial Tower. Lanesborough is another access point for Greylock and also has scenic lakes.

➡️ Stay here if you're a hiker who wants rugged outdoor adventures in the northern Berkshires.

🛏️ Where to stay in Adams: The Porches Inn at Mass MoCA 🌟 8.7 'Excellent' 🐶 Dog-friendly

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Conclusion:

Whether you’re planning a trip to the Berkshires for the first time or coming back to explore more, each region offers its own charm and highlights.

I took my years of experience living in the Berkshires along with my frequent recent visits to provide this 'best of the Berkshires' post.

I hope this guide helps you discover the best towns in the Berkshires and inspires you to plan the perfect trip!

Feel free to leave any questions or comments below - I'd love to hear from you! 🙂

Happy exploring and happy trails! 🐾🐶🌸