The 7 Best Towns to Visit in the Berkshires

Seven of the best and most popular towns in the Berkshires to visit. Add these to your itinerary to experience the best of what the region has to offer.

You’ve heard the Berkshires are a spectacular region to visit in Massachusetts – full of natural beauty, art, culture, and quaint New England towns.

But you’re probably wondering which Berkshires towns are worth visiting.

Nearly every stretch of this westernmost Massachusetts county is stunning with rolling hills and charming villages sprinkled throughout.

But there are a few Berkshire towns that really stand out – not only for their aesthetic beauty but for what they have to offer within them.

Below we share the 7 best Berkshires towns to focus your itinerary on when you visit. But before we get started, let’s get better acquainted with this area.

Where are the Berkshires?

In the United States, the Berkshires are the westernmost county in the state of Massachusetts.

To the north, Berkshire County borders Vermont, to the west it borders New York State, and to the south, Connecticut.

The region to the east of the Berkshires is known as Pioneer Valley which is a portion of the Connecticut River Valley. It consists of the Massachusetts counties of Hampden, Hampshire, and Franklin.

Like most other governmental counties in Massachusetts, Berkshire County has no active legal governmental or legal function. It only serves as a historical geographic region except for certain offices such as sheriff and registry of deeds.

The U.S. Berkshires are named after Berkshire County in southern England, the former home county of Sir Francis Bernard who served as the royal governor of Massachusetts from 1760-1769 and named the county.

While the written name, Berkshire, is the same in both countries, the British pronounce it Bark-sheer while Americans say Berk-sheer.

A Map of the Berkshires

This map illustrates where the Berkshires are in relation to the rest of Massachusetts. It also highlights the location of the seven best towns to visit in the county.

What are the Berkshires known for?

First and foremost the Berkshires are known for its natural beauty.

Western Massachusetts is known for its gentle rolling hills, that while less dramatic than the mountain ranges of Vermont or New Hampshire, still feature wide-sweeping, dramatic vistas that come alive with vibrant color in fall.

It’s from this backdrop you’ll find some of the most charming villages in New England – another characteristic of the Berkshires. Each community showcases an assortment of architectural styles and time periods, reminiscent of previous eras gone by.

The picturesque setting of the Berkshires is what inspired wealthy families in the late 19th and early 20th century, a time known as the Gilded Age, to make the Berkshires their late summer retreat. Today, the legacy of these opulent mansions and gardens lives on in the form of museums and tourist destinations.

While an art community existed before the Gilded Age, it was during this period that the Berkshires also became known as a destination for artists and art lovers alike. An influx of wealth brought with it support for the arts and this small region boasts an oversized number of impressive museums, performing arts venues, and is the summer home of the Boston Symphony Orchestra.

Today, former city dwellers from New York and Boston in particular, have made the Berkshires their home. With them, or among them, has come an influx of culinary expertise resulting in exquisite farm-to-table restaurants, cozy cafes, and a number of food coops and farmer’s markets.

The best towns in the Berkshires to visit

You’ll find beauty around every corner of the Berkshires, but there are a few towns in particular that draw the most visitors each year. These communities have well-regarded cultural attractions, shopping, restaurants & cafes, and the most popular hiking spots or outdoor recreation.

Listed by popularity (with our preference mixed in) here are the seven best Berkshire towns to explore when visiting.

Lenox

Nearly anyone who has spent a small amount of time in the Berkshires has most likely visited Lenox.

Located just south of central Berkshire County, this community is where wealthy industrialists primarily set up their summer homes during the Gilded Age. This influx of cash during the late 18th and early 19th centuries not only developed the cultural and artistic center of Lenox but also put it on the map as a popular tourist destination.

While Lenox’s small downtown is walkable and full of art galleries, high-end clothing boutiques, cafes restaurants, and a bookstore, the village is most well known for its cultural attractions, including the Tanglewood Music Center, Edith Wharton’s historic home The Mount, and the historic Ventfort Hall Mansion & Gilded Age Museum, among others.

See related: Top 15 Best Things to Do in Lenox Massachusetts

Great Barrington

Great Barrington is often considered the second most popular town to visit in the Berkshires.

Unlike Lenox which has more of an old-money vibe, Great Barrington is a mix of Brooklynites, locals, and former hippies. Wandering through the downtown you’ll find high-end clothing stores, art, gifts, and housewares – on par with what you’d find in urban retail establishments.

The hippie vibe can be seen in rainbow-painted crosswalks, the well-stocked Berkshire Food Co-op, and an outsized number of cannabis dispensaries. High-end restaurants also line Main and Railroad Streets, as do cafes, coffee shops, and a local ice cream shop.

Hiking enthusiasts will also want to check out Monument Mountain‘s trails. This mountain, the name of which is derived from Mohican tribe stone offerings, also ties to Herman Melville, William Cullen Bryant, and Nathaniel Hawthorne.

See related: Top 15 Best Things to Do in Great Barrington Massachusetts

Williamstown

Williamstown is most definitely at the top of the best Berkshire towns to visit.

This small community has it all – with its definitive New England college campus, a red brick building downtown, world-class art museums, and excellent hiking opportunities – all set against stunning rolling hills in the backdrop.

Art lovers, in particular, will enjoy a visit here with The Clark and Williams College of Art Museum exhibiting works from celebrated artists such as Pierre-Auguste Renoir, Sandro Botticelli, Claude Monet, Edgar Degas, John Singer Sargent, Edward Hopper, Winslow Homer, and contemporary artists, to name a few.

And hiking enthusiasts will want to check out the magnificent Mount Greylock, the highest peak in Massachusetts. Views from the top of Mount Greylock stretch as far as 90 miles in the distance. And a variety of hiking trails are suitable for both novice and experienced hikers.

Simply strolling through the Williams College campus and the small downtown is a delight unto itself. Although you won’t find as many high-end stores here as you would in Lenox or Great Barrington, the selection is still alluring. A few casual restaurants and an ever-popular coffee house round out the downtown’s appeal.

See related: Top 15 Best Things to Do in Williamstown Massachusetts

Stockbridge

Nestled between Lenox to the north and Great Barrington to the south, Stockbridge is another popular town to visit in the Berkshires.

The biggest attraction in Stockbridge is the museum dedicated to Norman Rockwell, the painter and illustrator known for his heartwarming and nostalgic depictions of everyday life in the 20th-century U.S.. Here you’ll find hundreds of his renowned Saturday Evening Post covers and numerous paintings including a portrait of J.F.K. and Rockwell’s Four Freedoms series.

Stockbridge’s tiny downtown is also worth a visit whether it’s to admire the delightful historic buildings captured in Norman Rockwell’s Main Street Stockbridge painting, wander into a few shops or art galleries, or grab a bite to eat at the Main Street Cafe.

You’ll also want to carve out time to tour Naumkeag, a stunning Gilded Age mansion a short distance from downtown. And serious art enthusiasts will want to visit Chesterwood, the house of Daniel Chester French, the sculptor of the statue of Abraham Lincoln at the Lincoln Memorial in Washington, D.C..

See related: Top 15 Best Things to Do in Stockbridge Massachusetts

West Stockbridge

West Stockbridge isn’t as well-known as the previous towns mentioned, but this sweet community is well worth a stop.

One of the central points in town is No. 6 Depot & Cafe, serving some of the best coffee you’ve ever tasted. Located in a former train station, this roastery and cafe is a hub of the community with friends, families, and coworkers meeting over a latte or espresso.

On Main Street, a short distance away, you’ll also find a couple of interesting art galleries, a Shaker furniture store, an antique gallery, a used bookstore, and the Public Market – a good place to pick up a sandwich and drink.

If you’re up for a bit of an artistic adventure, stop by TurnPark Art Space’s sculpture park on Moscow Street. Donations of $10 are requested for a self-guided tour of the property.

North Adams

A former mill town, North Adams is almost double the population of neighboring Williamstown and still a little rough around the edges after the collapse of his industrial center. But undoubtedly, North Adams is worth a visit – especially if your itinerary includes the north of Berkshire County.

Mass MoCA, the largest contemporary art museum in the United States if not the world, is the largest draw in North Adams. Here, you’ll experience art like never before. Housed in an interconnected array of spacious former fabric mills, Mass MoCA allows artists to show works unbounded by the restrictions of traditional museums. Popular exhibits at Mass MoCA include Sol LeWitt’s Wall Drawing Retrospective and James Turrell’s Into the Light collection.

After visiting the museum, grab a bite to eat in one of the handful of eateries on the property or head downtown for a meal at Public Eat + Drink. If North Adams is the last stop on your trip and you’re heading back east, be sure to follow the Mohawk Trail and capture the view from the famous hairpin turn lookout as you leave the city.

Pittsfield

As the largest city in the Berkshires and its centralmost point, Pittsfield is a common stop for anyone traveling throughout the county.

While downtown Pittsfield is still up-and-coming, there are a number of cultural attractions in the city. First, there’s the Berkshire Museum which is an aquarium, natural history, and art museum in one and a great destination for families with children.

Another popular destination in Pittsfield is the Hancock Shaker Village – a living history museum showcasing Shaker architecture, lifestyle, and culture including 20 buildings and multiple acres of gardens and walking trails.

Downtown, you’ll also find a few art galleries and studios, a performing arts theater, and restaurants & cafes. There’s also a teen-run Farmer’s Market held on Saturdays during warm-weather months.

See related: Top 15 Best Things to Do in Pittsfield Massachusetts

How to decide which Berkshire towns to visit

While ideally you’ll visit all seven Berkshire towns on your trip, not every itinerary allows for such an extensive overview of the region. Here’s a breakdown of which Berkshire towns are best for you given your interests and desired activity.

If shopping and spending time in restaurants and cafes is at the top of your list, be sure to visit Great Barrington. While this downtown is small and certainly walkable, there are a variety of well-appointed retail and culinary options to choose from here.

Museum goers and those interested in visiting Gilded Age mansions will want to spend time in Stockbridge and Lenox. These communities have a plethora of art museums, performing arts venues, and the famous Tanglewood, the summer home of the Boston Symphony Orchestra. There are also a handful of mansions in these towns that serve either as museums or hotels.

Art lovers – and particularly those interested in world-class artists and contemporary art – will want to carve out time to visit Williamstown and North Adams. While these communities are a bit of a distance from Lenox and Stockbridge, they pair well by rounding out the art viewing options in the area. A stop at the Berkshire Museum in Pittsfield is also a welcome attraction while traveling between these two areas.

And finally, if hiking or outdoor recreation is high on your list of things to do, nearly every community on this list has much to offer. While spectacular views can be seen from nearly every hill or mountain climb in the Berkshires, it’s worth noting that the climbs get steeper, and the views more extensive, the further north you travel in the county.