Summer Weekend in the Berkshires

By Yankee Magazine

Apr 18 2019

Summer Weekend in the Berkshires | Weekends with Yankee

Jacob’s Pillow Dance Festival in Beckett, Massachusetts.

Photo Credit : Christopher Duggan (Mark Stuart Dance Theatre)
Don’t let the bucolic hillscapes fool you: The Berkshires region of Massachusetts may be serene, but it’s far from sleepy. It has grand house museums, a groundbreaking contemporary art mecca, and restaurants that can give chefs in Boston a run for their money. And in the summer the Berkshires come alive with world-class dance, theater, and music performances — all in all, it’s more than enough to fill a perfect weekend getaway. Here are some of our favorite ways to spend a summer weekend in the Berkshires. For even more travel inspiration, check out episode 4 in season 3 of Weekends with Yankee, in which Yankee senior food editor Amy Traverso helps pack the perfect picnic for an evening of music at Tanglewood.
Summer Weekend in the Berkshires | Weekends with Yankee
Jacob’s Pillow Dance Festival in Beckett, Massachusetts.
Photo Credit : Christopher Duggan (Mark Stuart Dance Theatre)

Plan Your Perfect Summer Weekend in the Berkshires

5 Essential Things to Do in the Berkshires

Jacob’s Pillow Dance Festival | Becket

The gorgeous Berkshire Hills provide the backdrop for America’s longest-running dance festival, which features more than 350 performances and related events — talks, films, classes, tours, and more — from mid-June through August.

Mass MoCA | North Adams

After opening in 1999, this contemporary art museum sited in a former factory complex quickly became one of the nation’s premier cultural institutions. Don’t miss the Sol LeWitt retrospective: more than 100 large-scale wall drawings displayed throughout three stories of a grand old mill building.

Tanglewood | Lenox

Though New England’s most famous fresh-air concert venue is the summer home of the Boston Symphony Orchestra, its festival season (mid-June through August) encompasses much more than classical music. The Boston Pops show up here, too, along with acclaimed performers from the worlds of pop, rock, folk, and international music.

Hancock Shaker Village  | Pittsfield

Step into the pure and simple rhythms of a community that relied upon the land at this beautiful restored 19th-century village and working farm, which was among the largest and most successful of Shaker communities that once stretched from Kentucky to Maine.

Ramblewild  | Lanesboro

Elevate your playtime at this aerial adventure park set among the treetops and filled with ropes, bridges, ladders, and swings. There are five levels (beginner to advanced) represented in eight courses, some of which soar over ravines by way of zip lines.

3 Places to Stay in the Berkshires

The Gateways Inn | Lenox

Built in 1912 as a summer escape for Procter & Gamble heir Harvey Procter, this mansion has been transformed into a truly memorable bed-and-breakfast inn. Just a mile and a half from Tanglewood, it offers 11 rooms, including some with sleigh beds or fireplaces.

Bascomb Lodge | Adams

A sprawling 1930s stone-and-timber lodge at the 3,491-foot summit of Mount Greylock, Bascomb Lodge offers simply furnished private bedrooms and group bunk-bed rooms, terrific farm-to-table cooking at its dining room, and arguably the finest views in the Berkshires.

The Red Lion Inn | Stockbridge

The world is full of verandas and front stoops, but there’s hardly a front porch comparable to that of the c. 1773 Red Lion Inn. Accommodations include rooms in the historic main inn and its “modern country” guesthouse Maple Glen, as well as a variety of individual village houses.

5 Restaurants to Try in the Berkshires

20 Railroad Public House | Great Barrington

In a cozy space dominated by exposed brick and warm wood, enjoy a meal made with meats and produce sourced from a long list of regional farms. Don’t miss the burger, made from a custom grind of short rib and brisket.

Prairie Whale | Great Barrington

At this hip, rustic restaurant set back from busy Main Street, the daily-changing dinner and weekend brunch menus transform local ingredients into such delicacies as brick chicken with roast turnip, apple, and rosemary, and peach-polenta upside down cake.

Haven Café & Bakery | Lenox

A local favorite for breakfast and lunch fuel-ups — plus weekend brunches — Haven does sweet (ginger-cardamom scone, croissant French toast) and hearty (breakfast burritos, Vermont cheddar on grilled farm bread) equally well.

Mezze | Williamstown

The go-to spot for Williamstown Theatre Festival patrons, Mezze has a simple yet refined menu of snacks, small and shared plates, and entrées — not to mention sinful desserts that include scoops from Great Barrington’s SoCo Creamery.

Jack’s Hot Dog Stand | North Adams

Cheap eats don’t come any tastier than at this family-owned lunch counter. The top dogs: “with everything” (mustard, relish, onion) and “chili cheese” (a dog wrapped in American cheese and slathered with house chili sauce).