The Berkshires are well known as a fall destination for their colorful foliage, but a winter or spring escape could be just as adventurous. With such a variety of things to do indoors and outdoors in this rural region in the mountains of western Massachusetts, Pick and choose from the many options, all while having some of the most delicious drinks and food that New England has to offer.
Berkshire County – founded in 1761 at the western edge of Massachusetts – encompasses towns such as Williamstown, North Adams, Pittsfield, Lenox (my hometown), Stockbridge, and Great Barrington. These small towns run north to south, abutting Vermont, New York to the west, and Connecticut. The Berkshires are known for their arts and culture scene, with museums and galleries packed into historical town centers. Outside of these central hubs, there are thousands of miles of hiking trails, many leading to and from the Appalachian Trail. I always get hungry after a hike, and find that there is no shortage of delicious fresh food from local farms, restaurants, and bakeries.
Where to Stay
The Berkshires offers a complete array of accommodations. From camping (or glamping) sites, to chain hotels, to posh establishments, historically known as The Berkshire Cottages.
Camping is best done at one of the many State Forests, such as Mount Greylock, Pittsfield State Forest, or Savoy Mountain. Mt. Greylock is a favorite as the campground sits at the base of the tallest mountain in Massachusetts, and an iconic stop along the Appalachian Trail (at nearly 4,000 feet). Reservations can be made at Reserve America. There are primitive tent sites, RV site options, and even yurts and cabins at some of the forests. Here is a link on how to set up an account and reserve your campsite.
Find top campgrounds in Massachusetts for your adventure.
While camping is our usual go-to for travel, the Berkshires is one place you could splurge on your stay and have a true Gilded Age experience. Picture wealthy New York City industrial-era socialites escaping the hustle and bustle of city life while relaxing in and around one of the sprawling estates they owned just a short train ride east. Properties like Cranwell, Wheatleigh, and Blantyre speckle the landscape of The Berkshires and offer lavish accommodations with luxurious spas and restaurants on site.
What to Do & Where to Eat
Once you decide on where you will stay, start filling up your daily agenda with stops in many of the towns:
Williamstown
Home to Williams College, The Clark Art Institute, and Water Street. Before going into town, stop at Wild Soul River for some morning coffee or tea, and take in their curated shop offering herbs, books, tarot cards, and even Reiki energy treatment. The Clark Art Institute is an essential stop. It offers an impressive gallery of American and European paintings and the opportunity to walk miles of trails on its lush 140 acres. Water Street will fulfill both your shopping and eating needs with small shops and excellent options for lunch, such as The Spring Street Market and Cafe.
North Adams
Home to MassMoca, Natural Bridge State Park, and some impressive outdoor sculptures. North Adams is an up-and-coming spot in the Berkshires. MassMoca ranks as one of my all-time favorite museums for the way its revolving contemporary art exhibits ignite curiosity and demand exploration. Natural Bridges State Park offers an accessible walk to see some of the naturally carved gorges and is home to the only white marble arch in North America. After activities, check out PUBLIC Eat+Drink for both its ambiance and macaroni and cheese.
Pittsfield
We locals generally know Pittsfield as “the hub” of Berkshire County, linking north and south county together. Pittsfield offers a selection of chain stores and restaurants alongside buildings that formerly housed General Electric workers. Pittsfield is reinventing itself with more opportunities to experience the central point of The Berkshires. Take some time to stop here, stroll down North Street, and imagine it 50 years ago, when the streets were crowded with GE employees just having received their paycheck and going to eat and shop in the lively downtown area. A favorite weekend activity is to visit the Pittsfield Farmers Market, located just a few blocks from downtown.
Places like Wander, a new coffee shop, performance space, and gallery, are literally changing the course of Pittsfield’s offerings. I stopped in for a coffee and pastry one morning. I was lucky enough to see that they are building and connecting the community through almost daily events, such as silent dance parties, craft clubs, and professional networking events. I ended up going back several times during my stay, got to meet the owner, Jay Santangelo, and attend an LGBTQ+ business networking event there.
Lenox
My hometown of Lenox is home to world world-famous Tanglewood Music Center, many of the aforementioned Gilded Age Estates, and the sweetest small downtown area you may find anywhere. I spent every Fourth of July listening to James Taylor play before the fireworks over Stockbridge Bowl Lake. Beyond its concerts (summer home to the Boston Symphony Orchestra since 1937), Tanglewood offers stunning gardens and grounds, all open to the public year-round. Tanglewood is only a short drive from the four main blocks that make up the downtown area. Find any one of the small bistros along the street and enjoy a snack or meal while people watching.
Not technically in Lenox (although they originally branded their location there for the prestige associated with the town), High Lawn Farm has recently opened its doors to visitors. Late winter is a magical time on the farm because many baby cows are born and raised right there. I was able to visit a 12-hour-old baby cow, many juveniles, and then head over to the milking barn before stopping in their shop, filled with milks, cheeses, and homemade ice cream.
Stockbridge
This small town has a big flair. Stockbridge is one of my favorite places to walk with dogs, spend a day doing yoga, or grab one of the best chocolate croissants I have ever eaten. Kripalu offers day passes as well as retreat options for a variety of needs, all centering around wellness and movement. While I was there, I spent the day doing yoga dance, spending time in the sauna, and walking the labyrinth in a guided meditation. Before I went to Kripalu, located on a grassy hillside overlooking Monument Mountain, I had one of the best chocolate Croissants of my life at The Lost Lamb. If you want to eat at an original Berkshires establishment for lunch or dinner, check out The Red Lion Inn.
Great Barrington
One of the most southern towns in Berkshire County, Great Barrington is my favorite foodie town. You can do every meal and snack and never leave town. Start with The Great Barrington Bagel Company, just minutes outside of town. Then drive in and walk around the shops, where you will find a focus on local art, especially at the Railroad St. Collective. There are also an abundance of chocolate, candy, and bakery options. Grab a light lunch at one of the many small establishments on Railroad St., but save room for ice cream at SoCo creamery. Dinner will follow, with a delectable meal at Cafe Adam.
Quiet & Quaint
This most recent visit to The Berkshires was especially enlightening for me as I perused the many new LGBTQ+ owned businesses and organizations that have popped up throughout the region. Having grown up in this area, I often felt isolated from my community, so it brought a special bit of joy to my heart to see diversity and inclusion at the heart of The Berkshires experience.
New England boasts some of the most pastoral views, small town vibes, and cultural experiences of anywhere we have been in the United States. We find ourselves drawn to the slow and steady energy that New England embodies through its deep historical roots and focus on the natural beauty that lies along the Appalachian Range.
