Stockbridge

Above: Stockbridge General Store. Opposite page: Winterlights at Naumkeag.

familiar, that’s thanks to Norman Rockwell, who spent his last 25 years living and working right in the heart of town. The beloved painter of small-town American life created some of his most visionary and socially engaged work here. At his death, he bequeathed his studio, archive, and many paintings to what became the Norman Rockwell Museum, on 36 acres outside the town center.

EAT/DRINK | Everyone is welcome to occupy the classic rockers on the front porch of the venerable The Red Lion Inn (a favorite Rockwell subject), where you can order a craft cocktail while soaking up the view. Or, savor a meal at the formal Main Dining Room (reservations recommended) or more casual Tavern. Downstairs, The Lion’s Den has reopened post-renovation.

Main Street Café is a hop-step from the Inn for breakfast and lunch, or head across the street to The Lost Lamb, “a French-style patisserie and snackerie” that offers daily soups, salads, and sandwiches— plus macarons! After an extended hiatus, Once Upon a Table is open again and with a new owner, new chef, and a brand-new look. The restaurant offers seasonal fare in a cozy setting, tucked away in The Mews, just off Main Street. Sweet tooths will want to check out Peace, Love & Chocolate, right next door, and the newly opened Mielke Confections (it’s the GB store’s second spot). Just off Main, Stockbridge Coffee & Tea is a gathering spot for locals who chew on the news of the day—and pastries from Soma Catering—whilst perusing the gently used books in the adjoining bookstore. Tiffany’s Café has taken up residence at the Elm Street Market, complete with a lunch counter and grocery provisions. Michael’s Restaurant serves lunch and dinner seven days a week.

The Elm Street location of Nejaime’s Wine Cellar (sister store to the one in Lenox) has an extensive wine and craft beer selection.

SHOP | Souvenirs and tchotchkes are in plentiful supply at the Stockbridge General Store on Main and Sidetracks on Elm. Also on Elm: In existence since the 1790’s, Williams & Sons Country Store is an old-fashioned emporium with an abundant selection of penny candy, games, puzzles, and so much more. Schantz Galleries has an impressive display of contemporary glass art (by reservation only). Casablanca South is an offshoot of the main store in Lenox, specializing in fashion for women and men.

Back on Main, scope out the vintage vinyl (and CDs!), signage, and clothing at Seven Arts Gift Shop. Prado De Lana Sheep Farm Yarn and Wool is a family-run sheep farm specializing in wool products from its own flock. And Pittsfield’s Township Four creates beautiful floral arrangements and proffers a curated selection of plants and gifts.

Lastly, see the unique array of trinkets at Heirlooms Jewelry, in the same location for over a half century.

SEE | When the railroad arrived in 1850, so did the wealthy summer folk. Artists and writers came too, among them Daniel Chester French, sculptor of the Lincoln statue at the Lincoln Memorial. French’s summer home and studio, Chesterwood, is open to the public.

Naumkeag, the summer retreat for the Choate family until they bequeathed it to The Trustees of Reservations in 1958. It’s a pleasant mile-drive up the hill from the town center and hosts seasonal events. Launched in 1934, the Berkshire Botanical Garden is among the oldest public display gardens in the Northeast. It offers workshops. lectures, and inspiration.

The Mission House is a National Historic Landmark and museum on Main Street that tells the story of the Mohicans and missionary John Seargent. It’s part of the self-guided walking tour of the town, as is the 1884 former Town Hall (depicted in Rockwell’s The Marriage License). The Stockbridge Library hosts discussions, readings, and other events.

The Berkshire Theatre Festival puts on shows at The Fitzpatrick Main Stage and Unicorn Theater in Stockbridge (as well as The Colonial Theatre in Pittsfield).

STAY | The Red Lion Inn has been providing lodging and food for more than two centuries and now encompasses other guesthouses on the property.

The Kripalu Center for Yoga and Health (reopened after a pandemic pause) affords residential stays that focus on yoga, wellness, and self-discovery.

The Inn at Stockbridge inhabits a refurbished 1906 Georgian-style estate. The antiques-filled rooms at Stockbridge Country Inn come with modern amenities.