Living in Massachusetts I hear about the small towns in the Berkshires a good amount. Whether it’s for hiking in the summer or for skiing in the winter, someone I know is always heading to the Berkshires.
So, what all is there to do in the Berkshires and where should you stay? Read on to learn the best stuff these towns in the Berkshires have to offer.
Where to stay in the Berkshires
You could stay at a different hotel for each of these small towns in the Berkshires. However, since many of the most popular things to do in the Berkshires are just a short drive from one another, I’d recommend parking it somewhere central and exploring from there.
There are many great places to stay in the Berkshires, but the most popular towns to base yourself are Stockbridge, Lenox, or Great Barrington. Here are some of the best hotels in each of these:
Red Lion Inn – Stockbridge, MA
The Red Lion Inn is your quintessential Berkshires hotel—historic, antique-y, friendly. This historic landmark opened as a small tavern back in 1773 and has since grown into one of the most popular hotels in the Berkshires.
Many of the most popular things to do in the Berkshires are just a short walk or short drive away. While here, eat at one of their three restaurants and bars, check out their library and garden, and swim in their outdoor pool.
People love the old décor and the comfort of the place, as well as its location for sightseeing. Check them out here: Red Lion Inn
Yankee Inn – Lenox, MA
If the aesthetic you’re going for is “a little bit less like my grandmother’s house,” then the Yankee Inn is for you.
While many of the Berkshires hotels fancy that antique, lace curtain style, the Yankee Inn is more of a modern lodging situation. (With just a touch of lace, I guess they can’t help it.)
The Yankee Inn has a Superb guest rating, both an indoor and outdoor pool, 24-hour fitness center, 24-hour business center, and a bar/lounge. They offer free WiFi and free parking, as well as an incredibly friendly staff. Check them out here: Yankee Inn
Fairfield Inn & Suites – Great Barrington, MA
And if it’s absolutely no lace, no antiques, no four poster beds you’re looking for, the Fairfield Inn & Suites in Great Barrington is where you need to stay.
Though it lacks that characteristic Berkshires charm, the Fairfield Inn & Suites has everything you’re accustomed to: large indoor pool, simple rooms, a fitness center, a business center, and a 24-hour front desk.
They offer free WiFi, free parking, and even a free full breakfast. It’s your standard chain hotel but, with a Superb rating from reviewers, you’re sure to be pleased with your stay. Check them out here: Fairfield Inn & Suites
6 easygoing towns in the Berkshires
Now that you’ve chosen your base, it’s time choose which of these towns in the Berkshires you’re going to visit and what there is to do there.
1. Stockbridge, MA
Stockbridge, Massachusetts is one of the more well-known towns in the Berkshires and home to many of the area’s most popular sights and activities.
It’s primarily known for being the home of American painter Norman Rockwell and to walk down Stockbridge’s Main Street is to, quite literally, walk through a painting.
Stockbridge is said to be one of the quintessential American small towns and, if you’re coming from Boston (2 hours) or New York City (3 hours), this town will surely be a welcome sight.
Also check out: The Only Boston Bucket List You Need: 65+ Best Uniquely Boston Experiences (w/ Pro Tips!)
What to do in Stockbridge
Stockbridge is one of the many towns in the Berkshires big on history and art. Here are some of the best things to do in Stockbridge:
- Norman Rockwell Museum – home to the world’s largest collection of original Normal Rockwell paintings
- Naumkeag – Public garden, historic home, 48-acre “architectural masterpiece”
- Berkshires Botanical Gardens – 24-acre botanical garden featuring over 3,000 plant species
- Enjoy a meal at the Red Lion – The hotel mentioned above serves some delicious meals in some cool historic spaces.
2. Lenox, MA
Lenox, Massachusetts is mostly a summer destination as it’s the summer home of the Boston Symphony Orchestra (which I’ll get to in a second). And like many of the small towns in the Berkshires, Lenox couldn’t be cuter. Lenox is dotted with massive privately-owned mansions, historic libraries, and natural beauty.
What to do in Lenox
Lenox is home to one of the Northeast’s most popular festivals, among other things.
- Tanglewood Music Festival – The summer home of the Boston Symphony Orchestra hosts a variety of musical guests and performances.
- The Mount – historic mansion home of American author Edith Wharton (The Age of Innocence)
- Ventfort Hall – historic mansion and Gilded Age Museum
- Pleasant Valley Wildlife Sanctuary – Over 1,100 acres of forests, wetlands, and meadows; 7 miles of hiking trails; ponds and wildlife viewing
3. Great Barrington, MA
On its list of Best Small Towns in America, Smithsonian Magazine listed Great Barrington, Massachusetts as number one. On this list of easygoing towns in the Berkshires I have listed it as #3, purely by coincidence.
Besides that accolade, Great Barrington is known for a couple other points: being the birthplace of author and civil rights activist W.E.B. Du Bois, and for its plethora of antique shops.
It’s also popular for its dining scene. This small town in the Berkshires has over 70 restaurants—far more than a town this size should have. Apparently antiquing makes ya hungry.
What to do in Great Barrington
If antiquing isn’t why you came to town, rest assured there is more to this town than old furniture and knick-knacks.
- Monument Mountain hike – One of the most popular hikes in the Berkshires, said to be the inspiration for Herman Melville’s Moby Dick.
- Bash Bish Falls – 80-foot waterfall on the Massachusetts/New York border you can reach by hard trail or by easy trail.
Also check out: Visit Boston on a Budget: 13+ Ways to Save Money on Your Next Trip
4. Pittsfield, MA
Pittsfield, Massachusetts is known as the heart of the Berkshires and is the largest of all the towns in the Berkshires. (Population 47,000) It’s been featured on best places to retire lists and is even called the “Brooklyn of the Berkshires.” Clearly, it’s not as simple as many of the smaller towns in the Berkshires.
What to do in Pittsfield
Being the cultural center of the Berkshires that it is, you’re going to find a number of festivals, food and drink experiences, shopping, and many other ways to spend your days. Such as:
- Herman Melville’s Arrowhead – the former home of Moby Dick author Herman Melville
- Berkshire Museum – containing collections on fine art, natural sciences, ancient artifacts, and more
- Pittsfield State Forest – featuring 30 miles of trails for hiking, mountain biking, horseback riding, and more
- Hancock Shaker Village – former Shaker commune, now a living history museum
5. Chatham, NY
You read that right, not all towns in the Berkshires lie in Massachusetts. The Berkshires are actually located at the junction of Massachusetts and New York, down to Connecticut and up to Vermont.
And unlike the picturesque little towns of Massachusetts, Chatham, NY is something else entirely. More on the “pastural” side of things, this eclectic little town is a lot greener and a little more remote.
What to do in Chatham, NY
But like all the other towns in the Berkshires, Chatham is full of historic buildings and plenty of art and shopping experiences. Check out:
- Ooms Conservation Area at Sutherland Pond – Miles of trails, beautiful mountain views, birdwatching opportunities, and a variety of other outdoor activities
- Chatham Brewing – local microbrewery offering tons of beer and food
- Hudson Chatham Winery – Get your hand-made batches of wine, cheeses, and desserts here with beautiful Hudson Valley views.
- Check out some historical architecture – like the Crandell Theater and Union Station
6. North Adams / Adams, MA
Listed as the smallest city in Massachusetts, North Adams is easily one of the quaintest towns in the Berkshires. Adams and North Adams are just 10 minutes apart, and just 15 minutes from both the New York and Vermont borders.
What to do in Adams and North Adams
Though they may be small, they are home to some of the most popular things to do in the Berkshires. Like:
- Mount Greylock – popular hiking spot and the highest point in Massachusetts, also part of the Appalachian Trail
- Massachusetts Museum of Contemporary Art – For something quite different than many of the art museums in the Berkshires
- Natural Bridge State Park – home to the only natural white marble arch in North America (made from 550 million-year-old marble)
More info for your trip to the Berkshires
- Where to stay: Read reviews and find great places to stay here.
- Car rentals: Check out the best area rental car deals here.
- Pick up this New England guidebook before you go!
- Want more New England? Check out these posts.
Like this post? Have questions? Let me know in the comments! Enjoy your time in the Berkshires!
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