Kick things off with a visit to the Norman Rockwell Museum (the iconic painter spent much of his life in Stockbridge). Located on the edge of town, the museum maintains the largest single collection of the artist’s works — including every one of his Saturday Evening Post covers. Docents deliver an engaging presentation in the main exhibit hall every couple of hours. Afterward, your best bet is to take the self-guided audio tour, which allows you to hear insightful commentary on most of the displayed works at your own pace. Rockwell’s studio — which was preserved when he died — was relocated from his Stockbridge home to the museum grounds and is a highlight of the tour.
Head back to the center of town for lunch at the Main Street Café. The airy, wood-paneled dining room provides an inviting backdrop for hearty, homemade fare. Save room for dessert at the adjacent Stockbridge General Store, which serves to-die-for locally made ice cream from SoCo Creamery.
Walk the Main Street immortalized by Rockwell and check some of the town’s retail highlights, including the Seven Arts Gift Shop for music and eclectic pop-culture memorabilia, Williams & Sons Country Store for vintage and retro toys, games, candy, kitchen gadgets, books, and cards; and Peace Love and Chocolate for some sweet treats. Take a photo of the now-defunct Alice’s Restaurant, made famous by Arlo Guthrie’s debut album (and subsequent film). When you’re ready for a break, head to the corner of the block and have a drink at the Red Lion Inn. Anchoring Stockbridge’s Main Street since 1773, the inn has welcomed visitors for more than two centuries. Enjoy your drink by the fire in the inn’s parlor or sit outside on the inn’s iconic, bustling porch and take in a little people-watching.
Around the corner, Schantz Galleries on Elm Street, displays a breath–taking collection of glass art by Chihuly, Ries, Tagliapietra, and others. Stop next door at Nejaime’s Wine Cellar, and have them recommend a bottle or two to take home with you.
Go back in time, in style, by visiting Naumkeag, one of the few surviving and best-preserved summer “cottages” from the Berkshires’ Gilded Age. Take in the views from Naumkeag’s collection of enchanting gardens before touring the 44 rooms of this architectural gem.
End your day with dinner at Once Upon a Table, a cozy restaurant tucked away in an alley just off of Main Street, or head back to the Red Lion Inn for a traditional New England dinner in its main dining room or adjacent tavern. Stockbridge Through the Seasons: Stockbridge makes a wonderful day trip at any time of the year, with botanical gardens and outdoor arts-and-crafts fairs in the warmer months, and a popular harvest festival in October. In December, a living recreation of Rockwell’s Main Street at Christmas painting is staged, with vintage cars, food, drink, and entertainment.