The Berkshires are a perfect New England weekend getaway if you’re looking for a place on the East Coast to leave the everyday behind and enjoy nature and the simplicity of small towns.
They’re in Massachusetts and northwestern Connecticut. The Berkshires have long been a popular vacation destination for people from New York and Boston, many of whom have second homes there. Others, like me, are attracted by the peaceful atmosphere of the region and come from further away.
The Berkshires’ small towns have an old-world calm and serenity, perfect for those seeking a slower pace and a connection to the outdoors. I visited the area to visit Kripalu, a retreat center for yoga, health, and holistic living, in Stockbridge, Massachusetts and did some exploring while there.
Getting to the Berkshires
You’ll need a vehicle to visit this area. I drove the winding roads that curved around forests and lakes. Cresting and descending the many hills made for a fun and lively drive that held my attention, and it had all of mine.
My imagination was captured by dense forests, clear lakes, and long, grassy lawns leading to Gilded Age estates hidden in the trees. I drove past farmland, open fields, historic barns, and happy-looking livestock. Occasionally, a quaint, historic town or village would appear and drift past, each unique with character. Picture a white-steeple church, a mercantile, a town center, historic homes and small cafes with outdoor umbrellas.
But maybe you want to stop? I’ve got a few ideas.
Stockbridge
If you’re a fan of Norman Rockwell, the Stockbridge Main Street will look familiar. It’s probably how they came up with the word picturesque. It can feel more geared towards tourism centered around its main attractions or like Michael J. Fox when he went “Back to the Future.”
Still, this is a good place to stop for an entire afternoon. You can browse the many galleries and shops and have lunch at a local eatery.
Not into shopping? Hang out by Lake Mahkeenac for swimming, boating, kayaking, and fishing. There’s a public boat launch and a town beach. Yes, it’s all very scenic. Norman Rockwell wasn’t exaggerating.
Things to do:
- Norman Rockwell Museum: It houses the most extensive collection of Norman Rockwell paintings, illustrations, and even his (relocated) studio.
- Chesterwood: Tour the grand summer home of sculptor Daniel Chester French, best known for creating the Lincoln Memorial.
- Naumkeag: A 44-room “cottage” on eight acres with formal gardens that are a sight to behold. Puts the “gilded” in the Gilded Age.
- Berkshire Botanical Garden: A 24-acre garden. They often offer yoga and tai chi classes.
- Kripalu Center for Yoga & Health: A renowned yoga and wellness retreat center.
West Stockbridge
Stockbridge has the classic Berkshire experience with its famous museums, historic landmarks, and scenic lake. West Stockbridge is smaller, laid-back, very walkable and has a bubbling creek running through it.
- The TurnPark Art Space is a unique outdoor sculpture park built on a former marble quarry site.
- West Stockbridge Historical Society Museum: Learn about the history of the town and its industrial past, particularly its marble quarrying industry.
- Hiking: You’ll find access trails from a favorite scenic stop, Olivia’s Overlook.
- Shaker Mill Pond: A local place for canoeing and kayaking.
- Stevens Glen: A scenic area with a hemlock forest.
Lenox
Lenox is known for its abundant Gilded Age mansions, vibrant arts scene, and preserved natural surroundings. It’s the type of place that makes me wonder why I was born so poor. It has an “old-money” feel and features high-end boutiques, antique shops, and art galleries. Just visiting will make you feel more sophisticated and enriching.
If you visit on a concert night, you’ll hear the music from the Boston Symphony Orchestra wafting through town; Lexon is their summer home. If you dine in one of the cafes, you may hear some Shakespearean verses. A renowned theater company is housed here. It’s that kind of place. Here are a few things to do:
- Tanglewood: World-class classical music performances from the Boston Symphony Orchestra and popular artists’ concerts in a beautiful outdoor setting.
- The Mount, Edith Wharton’s Home: Tour the historic house and gardens of the Pulitzer Prize-winning author.
- Shakespeare & Company: The famed theater company presents a variety of plays, dramas, and comedies.
- Berkshire Scenic Railway Museum: Take a scenic train ride through the countryside. They offer various themed rides and special events.
The uniqueness of the Berkshires lies not only in these cultural offerings and their well-maintained historic charm but also in their abundance of natural splendor. The Lenox area has several natural areas. These include the Pleasant Valley Wildlife Sanctuary, with 1,000 acres of forests, meadows, and a beaver pond, Laurel Lake beach and boat launch and the nearby October Mountain State Forest, the largest state forest in Massachusetts.
Great Barrington
While still a Berkshire town, this one diverges a bit with its progressive spirit. I mean, it has cannabis shops, which is definitely off-brand, but there’s something for everyone in the Berkshires. Often described as the “Brooklyn of the Berkshires” there are rainbow crosswalks and a generally more laid-back feel than other towns.
It makes sense. This is a college town of sorts. It’s home to Bard College at Simon’s Rock, an early college where students can begin their college education after the 10th. Also, I wish I’d been born smart, alas.
Great Barrington was home to W.E.B. Du Bois, an African American sociologist, historian, civil rights activist, writer, and editor. Du Bois co-founded the NAACP and fought for racial equality. The W.E.B. Du Bois Boyhood Homesite here is a National Historic Landmark.
Other things to do:
- Mahaiwe Performing Arts Center: A restored historic theater that hosts performances, including music, dance, theater, and film.
- Art Galleries and Studios: Great Barrington has a big art scene, with galleries for local and regional artists.
- Local Festivals and Events: The town is known for hosting popular gatherings.
Like the rest of the Berkshires, there’s no shortage of outdoor activities and natural beauty. The Housatonic River flows through Great Barrington, and many head here for kayaking, canoeing, and fishing. No Berkshire town is complete without a water feature and this one has scenic Lake Mansfield. It’s perfect for swimming, boating, and picnicking on weekend afternoons.
If you’re a hiker, Monument Mountain is the most popular destination in the Berkshires and has views of the Housatonic River Valley. You may have heard of those views from our old friends Nathaniel Hawthorne and Herman Melville. They used to like to hang out around here, too.
Fun Fact: Pick up a section of the Appalachian Trail here. Approximately 90 miles of the Appalachian Trail traverse Massachusetts, most of which lies within the scenic Berkshire Hills. There’s an access point near Great Barrington.
Reasons to Love the Berkshires Small Towns
Among the most appealing aspects of the area was the reverence for nature and lack of big-box consumerism. Each small town has farm-to-table restaurants, cozy cafes, and unique shops offering local produce and artisanal and hand-crafted goods. It’s not bargain shopping, but browsing can be just as enjoyable when you meet the people behind the work.
I enjoyed coffee at local roasters, stopped at many hand-crafted chocolate shops and an adorable cheese farm with the happiest cows and goats you’ll ever find. I had to yield for more than one big turtle to cross the road.
- Natural Beauty: So many lakes and trees make your nervous system sing with happiness.
- Local Character: Unique shops, restaurants, and cultural institutions give each town a distinct identity.
- Slower Pace of Life: Relaxed atmosphere of a bygone era.
- Hidden Gems: Businesses run out of homes and off-the-beaten-path attractions.
- Hiking, Boating, Biking: Numerous trails, including sections of the Appalachian Trail, offer something for all outdoor lovers.
- Culture: Even just walking through these towns is enriching with arts and history.
Tips for Exploring the Berkshires’ Small Towns
- Plan Your Route: Expect to find each town you pass through will have more than you expect to find. Plan to stop more often than you might on any other type of road trip.
- Support Local Businesses: Many small businesses pop up alongside the road. Be watchful and prepare to stop or turn around. You can find some of the most unique art and colorful characters here! I bought a great piece of pottery in a house on the side of the road.
- Check calendars for local events: These small communities are active all year round and often host farmers’ markets, festivals, parades and performances. Check websites in advance and plan accordingly.
These are just a few of the many small towns in the Berkshires. North Adams, Williamstown, Lee, Pittsfield, and others are also worth visiting. Each has its unique blend of history, culture, and natural beauty, offering a refreshing escape and a wealth of experiences worth discovering. Which Berkshires small town is your favorite?
Read more stories about Massachusetts here.
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