A Weekend at Tanglewood in the Massachusetts Berkshires

As the summer home of the Boston Symphony Orchestra, Tanglewood has provided music against a beautiful Berkshires backdrop since 1937 — picnics encouraged.

By Aimee Tucker

Jun 26 2019

Tanglewood Shed Picnic


Photo Credit : Aimee Tucker
In the beautiful Berkshires of western Massachusetts, the soundtrack to summer is provided by Tanglewood, the summer home of the Boston Symphony Orchestra and New England’s premier “concert with a picnic” destination since 1937. Tanglewood with Yankee Magazine I wrote about Tanglewood as a “Local Treasure” in the May/June 2015 issue (See: “Music with a View“), so I was delighted (along with fellow Yankee Kate Hathaway Weeks) to journey to Lenox last month to help kick off the summer season and distribute complimentary copies of the issue. Many folks like to arrive several hours before the concert begins so they can relax and picnic under the summer sun (the term “Tanglewood Tailgating” gets tossed around a lot), and what better New England reading material is there than Yankee? None, of course! Here’s a look at our two-day Tanglewood adventure. DAY ONE
Tanglewood Entrance
Welcome to Tanglewood in Lenox, MA!
Photo Credit : Aimee Tucker
We started the day with a guided tour, which are offered for free several times per week and led by a member of the Boston Symphony Association of Volunteers. Our friendly and knowledgeable guide, Howie Arkans, showed us around before the gates opened. It was a perfect summer afternoon, and strolling the grounds while listening to Sheryl Crow and her band (that night’s featured performer) do their sound check had us feeling like two of the luckiest ladies in New England.
Tanglewood Guide Howie Arkans
Our friendly Tanglewood guide Howie Arkans.
Photo Credit : Aimee Tucker
Howie told us the basics of Tanglewood’s long history. The Boston Symphony Orchestra (BSO) gave its first outdoor concerts in the region back in 1936. Then, that same year, the donation of the Tanglewood estate in Lenox (named for the 1853 Tanglewood Tales by Nathaniel Hawthorne) made it possible for then-conductor Serge Koussevitzky to officially found in 1937 the festival we know today as Tanglewood. In time, it grew. The Koussevitzky “Shed” pavilion opened in 1938, the Tanglewood Music Center began in 1940 as a school for young performers, and the grounds expanded by 40 percent with the 1986 addition of the adjacent Highwood estate. When you first walk through the main gates, you’re met with the sight of the Koussevtitzky Shed and its famous sprawling lawn. We asked Howie how many people they could fit at a concert, and he told us that they never had a limit for the lawn until the James Taylor shows started getting more popular than they could safely have room for, so now they cap the number at around 23,000.
Tanglewood Lawn
The Koussevitzky Music Shed at Tanglewood, with its famous (and impossibly green) lawn.
Photo Credit : Aimee Tucker
Under the shed, there are curved rows of wooden seats, and an overhang for the lawn folks in case of severe weather.
Tanglewood Shed Seating RS
Under the shed at Tanglewood.
Photo Credit : Aimee Tucker
Here’s a quick video showing the scope of the lawn while the BSO warms up with an instrumental version of “She’s Leaving Home” by the Beatles. Just a few hours later, the lawn was completely filled with colorful, joyful picnickers. Continuing along, we stopped at the Tanglewood Visitor Center, which glows from the inside like a Victorian dollhouse. Its front porch offers what many consider to be the best view at Tanglewood of the Stockbridge Bowl.
Tanglewood Visitor Center
The Tanglewood Visitor Center.
Photo Credit : Aimee Tucker
It’s no wonder that some folks choose to set up their picnics here to admire the views while the music drifts over from the adjacent Shed lawn.
Tanglewood View Stockbridge Bowl
The view from the porch at the Tanglewood Visitor Center.
Photo Credit : Aimee Tucker
Leaving the views behind, we passed Lion’s Gate entrance (marked by two lion statues) before arriving at one of Tanglewood’s on-site dining options, the Tanglewood Cafe. There’s also the option of pre-order picnics, a casual grill-style eatery near the main entrance, a Beer Garden, and more elegant dining at the Highwood Manor House, newly opened to the public for dinner Friday and Saturday, and Sunday brunch. At the Cafe, we especially recommend a cold brew iced coffee from Six Depot Roastery and Cafe (they also have a mobile cart near the main entrance), based in nearby West Stockbridge.
Tanglewood Cafe
The Tanglewood Cafe.
Photo Credit : Aimee Tucker
And here’s the Highwood Manor House, where more elegant buffet offerings are available on the weekends.
Tanglewood Highwood Manor House
Highwood Manor House at Tanglewood.
Photo Credit : Aimee Tucker
The views from the front lawn at the Highwood House aren’t bad, either.
Tanglewood Highwoood House View
The view from Highwoood Manor House.
Photo Credit : Aimee Tucker
Tanglewood’s second major concert space, Ozawa Concert Hall, was opened in 1994. During a performance, its wooden doors can be opened to offer the same lawn experience as the Koussevitzky Shed.
Tanglewood Ozawa Concert Hall
Ozawa Concert Hall, opened in 1994.
Photo Credit : Aimee Tucker
Tanglewood Ozawa Concert Hall Side
Ozawa Concert Hall.
Photo Credit : Aimee Tucker
Howie pointed out to us a few of the rehearsal buildings for students at the Tanglewood Music Center. It’s delightful to imagine the nondescript buildings tucked into trees emitting some of the most beautiful music in the world played by some of its most talented musicians.
Tanglewood Practice Area
A rehearsal space for students at the Tanglewood Music Center.
Photo Credit : Aimee Tucker
After thanking Howie for the tour, it was time to set up our table and get ready for the gates to open.
Yankee Table
We were on site to hand out complimentary copies of the May/June 2015 issue, which featured an article on Tanglewood.
Photo Credit : Aimee Tucker
Yankee Magazine at Tanglewood
Yankee Magazine Director of Brand Marketing Kate Hathaway Weeks and Digital Editor Aimee Seavey (that’s me!) at Tanglewood.
Photo Credit : Kate Hathaway Weeks
Yankee Magazine Tanglewood
What could be better reading material at Tanglewood than Yankee Magazine?
Photo Credit : Aimee Tucker
We were situated right as folks entered the grounds (between a popular ice cream stand and Sheryl Crow’s merchandise table), and it was great fun handing out magazines and watching the picnickers make a beeline for their favorite spot on the lawn. Some carried coolers, some beautiful vintage picnic baskets, and still others pulled wagons stuffed with chairs, tables, balloons, and even the odd candelabra. Picnics, I soon learned, are serious (but fun) business at Tanglewood.
Picnickers head to claim their spot.
Photo Credit : Aimee Tucker
The crowd was made up of every kind of music-lover. Young couples strolled in alongside entire families, kids cartwheeled across the grass, and a group of twenty-something girlfriends in cowboy boots followed on the heels of an older couple carrying an L.L. Bean tote bag with a baguette and fresh flowers sticking out of the top. Tanglewood is a party, and everyone’s invited.
Tanglewood Chair Rental
Traveling light? Chair and cushion rentals are available on site for a small fee.
Photo Credit : Aimee Tucker
Some picnickers laughed and joked as they ate while others readied themselves for a nice long late afternoon nap before the show started (although I don’t think napping during it is frowned upon, either). Drinking in the happy vibe, it’s clear why people love Tanglewood and look forward to coming back year after year, if not month after month, or week after week.
Tanglewood Tree
Picnickers set up under one of the stately Tanglewood trees.
Photo Credit : Aimee Tucker
Tanglewood Picnickers
Picnickers as far as the eye can see.
Photo Credit : Aimee Tucker
Tanglewood Crowd Couple
Lounging and laughing are both encouraged.
Photo Credit : Aimee Tucker
As the sun began to set and conductor Keith Lockhart came to the podium to welcome the crowd to “a perfect summer evening at Tanglewood,” everyone applauded and settled in to enjoy the show — a wonderful medley of Beatles songs performed by the Boston Pops followed by a fantastic set by Sheryl Crow, who repeatedly referred to her appearance as “a real treat.”
Tanglewood Sunset
Sunset settles over Tanglewood.
Photo Credit : Aimee Tucker
It was for us, too. DAY TWO We began our second day in the Berkshires with a tasty breakfast at our historic hilltop host resort for the weekend, Cranwell. A Tudor-style mansion (there’s a spa and golf, too), Cranwell dates back to 1869, and its lovely grounds were designed by famous landscape architect Frederick Law Olmsted.
Cranwell Berkshires
Cranwell Resort in Lenox, MA.
Photo Credit : Aimee Tucker
Re-fueled and ready for another beautiful day in the Berkshires, we had one clear mission — to build the perfect picnic to enjoy during that evening’s concert. In anticipation, I’d already picked up a beautiful basket from our New Hampshire neighbors at Peterboro Basket, but what to put inside? My initial bout of inspiration had come from local author Gina Hyams’ wonderful new book, The Tanglewood Picnic: Music and Outdoor Feasts in the Berkshires (Muddy Puppy Media, 2015). A delightful read for both newbies and seasoned Tanglewood pros, the book details more than 80 years of picnicking tradition with vintage photos, personal stories, and tasty recipes.
Tanglewood Picnic Gina Hyams
You’ll find “The Tanglewood Picnic: Music and Outdoor Feasts in the Berkshires” by Gina Hyams for sale at many locations throughout the Berkshires. We spotted these copies at Charles H. Baldwin & Sons in West Stockbridge.
Photo Credit : Aimee Tucker
We also asked our friend Stephanie (a proud local) to suggest a few places to pick up the best provisions, and she didn’t disappoint. Stops included the Downtown Pittsfield Famers’ Market for palm-sized cookies from Madeline’s, Chocolate Springs Cafe (the chocolate violins would be especially appropriate at Tanglewood), and Spirited for a bottle of local wine, cheese, and a fresh-baked baguette from Berkshire Mountain Bakery.
Pittsfield Farmers Market
Find local bread, baked goods, honey, produce, and more at the Downtown Pittsfield Farmers’ Market.
Photo Credit : Aimee Tucker
We also visited Guido’s Fresh Marketplace, a popular local spot for picnic provisions that Howie had recommended to us on our Tanglewood tour. If you’re looking for a one-stop shop that carries basic provisions plus the fancier things in life, Guido’s is a great bet. They had it all, from pre-packaged sides and plastic wine glasses to fresh fruit, meats, cheeses, wines, snacks, fresh flowers, and everything in between. We picked up some nuts, cherries, figs, grapes, Tre Olive olive oil (based in East Longmeadow, MA), crackers (including our Editors’ Choice Food Award winner Stonewall Kitchen Aged Cheddar Beer Crackers), and a few bottles of Black Cherry soda.
Guido's Fresh Marketplace Pittsfield, MA
Guido’s Fresh Marketplace in Pittsfield (there’s a location in Great Barrington, too) is a picnic packer’s paradise.
Photo Credit : Aimee Tucker
Cranwell, knowing of our Tanglewood plans, was also kind enough to put together two picnic lunches for us to take along. You get the distinct feeling in the Berkshires that, at every inn, restaurant, cafe, and roadside farm stand from Pittsfield to Great Barrington, there’s something for sale for picnickers. The corkscrew is as common in western Massachusetts as the lobster cracker is along the Maine coast. And finally, what picnic is complete without a blanket? If you forgot to pack one, or are just in the mood to get something new, there’s a Pine Cone Hill (an Annie Selke company) outlet store in Pittsfield that has a wonderful (and bargain!) selection of colorful textiles. We picked out a cheerful blue and white striped indoor/outdoor rug, and it worked beautifully. When it came time to head back over to Tanglewood, the sky had darkened and intermittent sprinkles were passing through. Taking advantage of the quiet pre-show atmosphere, I decided to wander over to the Shed once more to hear the BSO running through the evening’s performance, a tribute to Stephen Sondheim.
Tanglewood Rehearsal
Watching the BSO rehearse before a show at Tanglewood.
Photo Credit : Aimee Tucker
Tanglewood BSO Rehearsal
Practice makes perfect, and these guys are already the best of the best.
Photo Credit : Aimee Tucker
I also decided to check out the Tanglewood Formal Gardens, located beyond the Visitor Center. It’s amazing how quickly you feel like a kid again, wandering through a “secret garden” — there wasn’t another soul in sight. Just me and the wet grass and a tunnel of grape vines leading to the bust of great American composer Aaron Copland. Copland loved Tanglewood, and headed the composition faculty at the summer music academy for 25 years.
The Formal Gardens at Tanglewood
The Formal Gardens at Tanglewood.
Photo Credit : Aimee Tucker
Tanglewood Aaron Copland Bust
The bust of composer Aaron Copland in the Tangelwood Formal Gardens.
Photo Credit : Aimee Tucker
There’s also a “whispering bench” in the garden. If you whisper into one side of the bench, a person sitting on the opposite side will be able to clearly hear you.
Tanglewood Whispering Bench
The whispering bench in the Tanglewood Formal Gardens.
Photo Credit : Aimee Tucker
After another pre-show bout of handing out copies of the May/June issue and chatting with friendly Tanglewood patrons, it was time to set up our own picnic before the show began. Not a bad spread for a few first-timers, eh?
Tanglewood Picnic
Our Tanglewood picnic.
Photo Credit : Aimee Tucker
Then, as the sky began to darken, the show began. The bad weather (the rain continued to come and go all evening) likely kept a few folks at home, but the Tanglewood picnic faithful just donned their raincoats and camped under the trees.
Tanglewood Picnic
Our picnic ready, it was time to settle down and enjoy the show!
Photo Credit : Aimee Tucker
Listening to beautiful music, full of good food, and charmed by the glow of our neighboring picnickers’ paper lanterns, we agreed that Tanglewood was very magical indeed.
Tanglewood Lanterns
Another beautiful evening at Tanglewood.
Photo Credit : Aimee Tucker
Have you ever been to Tanglewood? What do you (or would you) pack in your picnic basket? Tanglewood. 297 West Street, Lenox, MA. 888-266-1200 (Tanglewood tickets); bso.orgThis post was first published in 2015 and has been updated.