Massachusetts
The Berkshires in Summer | My New England
From Tanglewood picnics to modern art, this collection of favorite things to do in the Berkshires in summer offers the perfect blend of old and new.

Coffee By Design | Portland, Maine
Photo Credit : Katherine Keenan
Photo Credit : Linda Campos
CONNECTING WITH NATURE
We spend a lot of time outdoors. Whether we’re hiking, swimming, or listening to a concert on the lawn, we aim to soak up as much of the scenery and landscape as we can. We’re lucky to have the Stockbridge Bowl in our back yard. This is where you’ll often find us kayaking, paddle boarding, or going for a swim at sunset. If you don’t have your own, you can rent kayaks and paddleboards from the Arcadian Shop in Lenox. They drop them off and pick them up daily from the boat launch in Stockbridge. If you prefer to hike, there are unique and captivating trails in abundance all over the Berkshires. Most hikes are pet-friendly and you can find some of our favorites here.
Photo Credit : Linda Campos
KRIPALU YOGA ON THE LAWN AT TANGLEWOOD
One of my favorite places to be on a Saturday morning in the Berkshires is at Tanglewood for Kripalu Yoga on the lawn. If you’ve never experienced outdoor yoga serenaded by the Boston Symphony Orchestra during their morning rehearsal, you’re in for a serious treat! This hour-long class boasts one of my favorite views of the Stockbridge Bowl and depending on the weather, a nice breeze to boot. The classes are free for ticket holders of the morning rehearsal and a great place to catch some sun or enjoy a shady spot under the trees during class.
Photo Credit : Linda Campos
EATING OUT IN THE BERKSHIRES
It’s no secret that I love to cook. My Instagram feed is littered with photos of local produce from neighboring farms and farm stands. I’m like a kid in a candy store waiting for each new crop to arrive at the farm. While summer cooking is a highlight for me, there are many great restaurants to try as well. No. Six Depot in West Stockbridge is my go-to lunch spot. It’s a favorite of many, so be prepared for long lines on the weekends. Some of my personal favorites are the Italian Tuna Salad, the Antalya Salad, and the Quinoa Salad, but it’s hard to go wrong when ordering off of their breakfast or lunch menu. The Bistro Box was a new find for us this summer and we can’t get enough of their grass-fed burgers. The Prairie Whale in Great Barrington is always on repeat with their scrumptious corn bread, farm-to-table vibes, and all around great atmosphere. Baba Louie’s in Great Barrington is the top request from my nieces and nephews when they visit. Some of my family members were on the verge of fighting over their gluten-free barbecue chicken pizza. And finally, for those special occasions, there is Nudel in Lenox. This is where we chose to celebrate my husband’s birthday dinner with friends. It’s seasonally inspired and we couldn’t be happier that they’ve started taking reservations this year.
Photo Credit : Linda Campos
A DAY AT THE MUSEUM | WILLIAMSTOWN & N. ADAMS
There is no shortage of cultural institutions in the Berkshires, but whenever my husband and I have a free day we like to drive north to either the Clark or Mass MoCA for some inspiration. Williamstown and North Adams are charming and quaint little towns and the drive reminds us of just how expansive the Berkshires are. The Clark collection features some impressive American and European artists, but I especially love the Winslow Homer collection. The museum’s outdoor spaces are also so relaxing that you won’t want to leave. I recommend lounging “pool side” in one of the many Adirondack chairs outside of the main building. The view is stunning and I can’t wait to go back during fall to enjoy the foliage. MassMoca’s long-term Sol LeWitt exhibition is a must-see when in North Adams. The vibrant colors and bold geometric shapes of his wall drawings are fun for grown-ups and children alike. If you have kids in tow, they’ll enjoy the artbar where they can experiment with making art projects.PICNICS ON THE LAWN AT TANGLEWOOD
Lastly, it wouldn’t be a summer night at Tanglewood without a picnic! If you’re a part of the BSO family, you tend to spend weekends on the lawn picnicking with friends and family. While many concert attendees bring their own personal picnics, a group of us regulars meet each week and call ourselves the Competitive Picnic League. It’s tons of fun cooking to a theme and as our name implies, trying to upstage each other with fancy table settings and impressive food. One of our most memorable recent picnic themes was Mad Men and the 1960’s. People brought their A-games with dishes like Baked Alaska, home brew brown ale fondue, and a Bloody Mary bar. While we’re serious about our food, more importantly, the league brings us together as a community, and that’s what I love the most. If you love to cook and share in local food experiences, you’re welcome to join us next summer!
Photo Credit : Linda Campos
Wow this looks so perfect! Saturday morning yoga is always amazing, and it’s so great to get back to nature!
Chelsea
This is a great list, thank you!
You’re welcome!
I agree with all these spots and can add to,it. Must stops for our visitors are Baldwin’s extracts in West Stockbridge, the Canaan general store in nearby Canaan NY, and the New Lebanon flea market on Subday mornings. MacHaydn theatre inChatham is fantastic Thayer in the round for musicals. Hikes to do include Bebee Hill fire tower in Canaan, and Ice Glen in Stockbridge, which also shares a trailhead with a lovely flat paved walk along the river. Check these out!
Those sound lovely! I always stock up on baldwins vanilla but have never checked out the general store in Canaan. Thanks for the tips!
Any list of things to do in the Berkshires should include the Norman Rockwell Museum in Stockbridge and Mount Greylock, the highest peak in Massachusetts. These are the places we like to take our first-time visitors to the Berkshires.
I love the Norman Rockwell Museum! It was difficult to narrow down all of the amazing sights in the Berkshires. ????
Wow, what a feast to the eye, spirit and the soul. Delicious taste to the imagination!