Country Retreat to The Berkshires

Culture & history

Spend an evening channeling the life and times of Edith Warton at The Mount & Gardens, her beloved country estate. Fridays and Saturdays throughout the summer offer live music and jazz, while fall is a great time to take a ghost tour of the home and property.

Tour the gilded age mansion and gardens of Naumkeag. If you happen to visit over a Thursday evening, stay for the live music and food.

A visit to Stockbridge isn’t complete without spending time in the history-filled halls of the Norman Rockwell Museum. Norman lived and painted for much of his life in this community and the largest representation of his work can be found lining the walls. Kids will appreciate the paintings of children their own age.

Live music

Jacob's Pillow is an iconic dance festival and historic landmark nestled in the Berkshires, with performances running all summer. They showcase a wide range of dance companies and styles, and entry is free. A must-do!

If Tanglewood is in season (June through August), be sure to catch a matinee at Seranak Cottage, the summer home of the Boston Symphony Orchestra since the 1930s. You can order a picnic online via their website, or head to Ne Jaime's Wine Cellars in Stockbridge for the best in gourmet fare – pre-packaged picnics or self-curated. They'll even pack your wine or beer on ice and provide serviettes and silverware.

Shopping downtown

Head to Great Barrington to poke around the sweet shops that line Main Street. One Mercantile for copper mint julep mugs, ceramics and salt water taffy, Rubiner's Cheese Mongers & Grocers for some funky fromage and of course, Tom's Toys.

Coffee, breakfast and snacks

At the Red Lion Inn, the blueberry pancakes reign supreme. Especially if you add a side of local Berkshire pork sausage. Be sure to pay a visit to the house cat and ride the old-timey elevator for a glimpse back in time.

Haven is beloved by all the locals, and a must-stop for seasonal, fresh and homemade baked goods, as well as breakfast fare.

Stockbridge Coffee & Tea: Their housemade roasts are some of the best in the Berkshires.

Fuel: Great breakfast and coffee await in this lofty brick-lined coffee shop.

The Scoop: Go for the heartbreakingly creamy ice cream and stay for the candy, fresh baked goods, and another cup of coffee.

SoCo Creamery: Get a scoop or two (or three) of their premium gelato, ice cream and sorbets, offered in inspiring flavors such as Blueberry Honey Lavender, Espresso Cookie and Alphonso Mango sorbet.

Lunch & dinner

Widow Bingham's Tavern: This century old dining room is part of the Red Lion Inn, and the pub has been satiating appetites for lunch and dinner since the 1800s. You'll enjoy hearty soups, fresh fare and savoury classics – plus a kids’ menu for picky minis.

Frankie's Ristorante Italiano: Offering casual and fun American Italian cuisine, this restaurant is especially welcoming of young families.

Table Six at the Kemble Inn: Grab a table on the grass and let your kids run amok across the vast lawn – it's enormous and inviting – while the adults enjoy a moment of peace and tranquility.

Prairie Whale: Former Brooklynite and well-known restaurateur, Mark Firth, has brought his farm-to-table cuisine closer to the farms themselves. Serving delicious, seasonal, hyper-local meat and produce, the menu changes daily. Best pick for a date night.