With its sublime forests and deep valleys, the Berkshires mountain range has long been a popular vacation spot for Bostonians and New Yorkers, who come for the world-famous arts scene, and increasingly, for the food, as more chefs — and curious foodie travelers — are drawn to the yields of its fertile farmland. Here’s how to enjoy the bounty on a weekend getaway with the best restaurants and things to do in the Berkshires.
Day 1: Farm-To-Table Friday Eats
Start your weekend with an educational tour of Hancock Shaker Village, a living history museum set on 750 green acres just 15 minutes south of Hancock and Pittsfield.
Interpreters dressed in traditional Shaker garb lead you through the Village’s complex of historic buildings, from the brick house and the meetinghouse to the weave shop and the tannery. It’s an especially fun day for families with little ones: You can watch chicks hatch, try on Shaker clothing, write with a quill pen, or take a 19th-century lesson from a Shaker teacher in the Schoolhouse.
Come lunchtime, walk over to the Village’s recently opened Bimi’s Café. Operating under the Shakers’ commitment to growing what you eat, Bimi’s is not your average museum-cafe. Many of the ingredients on the menu are plucked from the on-site farm.
Properly satiated, it’s time for a taste of the region’s celebrated arts scene. The Barrington Stage Company back in Pittsfield is best known for the 2004 world premiere of The 25th Annual Putnam County Spelling Bee, which moved to Broadway and won two Tonys.
This year, the theater is putting on several exciting shows: Eleanor (July 16-Aug. 1), starring Tony Award-winning actress Harriet Harris as Eleanor Roosevelt; Sister Sorry (Aug. 13-Aug. 29); and A Crossing (Sept. 23-Oct. 17). Catch one, and then some sleep.
Day 2: Leisurely Saturday Picnics
In the morning, head 35 minutes south to enjoy a walk-and-talk breakfast at the Great Barrington Farmers Market, which has been championing small local producers for 25 years and is the epicenter of the Berkshires food scene.
Your first stop: Strudel House for its hand-pulled pastry stuffed with sour cherries, blueberries, or apples. As you nibble, visit other vendors and pick up food to bring back to your resort to cook. You can’t go wrong. Sean Stanton of North Plain Farm sells pasture-raised sausage and eggs; Berkshire Mountain Bakery presents a charming array of flour-dusted sourdough loaves; and Justamere Tree Farm offers sustainably harvested maple syrup produced with 100% renewable energy.
As the day begins to wane, grab fixings for a picnic at Nejaime’s Wine Cellars or Guido’s Fresh Marketplace and enjoy an evening outdoor concert at Tanglewood, the storied summer home of the Boston Symphony Orchestra. For more than 80 years, it’s helped put the Berkshires on the map.
This summer’s season runs through late August, and highlights include an all-John Williams program featuring selections from Star Wars and E.T. (July 23); an all-Beethoven concert featuring violin soloist Joshua Bell (Aug. 7); and a performance of Tchaikovsky’s Variations on a Rococo Theme by cellist Yo-Yo Ma (Aug. 8).
Day 3: Wine Down On Sunday
Ease into your day at Hilltop Orchards & Furnace Brook Winery in Richmond, about 20 minutes west of Pittsfield and south of Hancock, where a red-and-white barn gives way to seemingly endless rows of apple trees. Visitors get a personalized, COVID-friendly cider and wine tasting experience. Take your glass of pinot grigio or “Bee My Honey” mead (and maybe a sugar-sprinkled apple cider doughnut) out onto the Normandy Gazebo to take in the view.
At the lush Lakeview Orchard over in Lanesborough, 15 minutes north of Pittsfield and east of Hancock, you’ll find a row of little red buildings (one is a cider mill), sprawling orchards, and homemade jelly doughnuts.
Or, see a performance at Jacob’s Pillow Dance Festival, the country’s longest-running international dance festival. Every year, it draws people from all over the world to its stunning 22-acre spread. The busy summer season includes LaTasha Barnes’s acclaimed Jazz Continuum series (Aug. 11-15) as well as Ballet Coast to Coast, featuring leading artists from Boston Ballet, Houston Ballet, and Pacific Northwest Ballet (Aug. 25-29).
You’ll need a reservation for brunch at the on-site Old Inn on the Green. With its farm-to-table food, creative cocktails, and view of the theater, the restaurant is a memorable last stop for your culinary weekend.