Massachusetts

Perfect Weekend In The Berkshires

Outdoors and in, the Berkshires of western Massachusetts have an appeal all their own. Our guide to the perfect Berkshires weekend is here to help inspire your next visit.

By Yankee Magazine

Sep 29 2016

Berkshire-Scenery,-photo-credit-Ogden-Gigli-A00A1293_R

The rolling landscape of Massachusetts’ Berkshires region comes alive with vibrant color each autumn

Photo Credit : Ogden Gigli
The rolling landscape of Massachusetts’ Berkshires region comes alive with vibrant color each autumn
The rolling landscape of Massachusetts’ Berkshires region comes alive with vibrant color each autumn
Photo Credit : Ogden Gigli

Tucked away along Massachusetts’s western border, the Berkshires combine classic New England appeal with stunning modernity and culture. Don’t be dissuaded by its rural appearance; the Berkshires have a lively arts and cultural scene to rival some of the largest surrounding cities. Though the area has enough world-class dining, lodging, and museums to keep visitors busy, this being October you’ll want to venture outdoors into the forests and mountains to explore the region’s true allure.

WHAT TO DO

BEST ART MUSEUM CAMPUS CLARK ART INSTITUTE, Williamstown

The opening last year of the Clark’s new Visitor Center was a capstone in the reinvention of this already-excellent small museum. The 19th-century French works collected by Sterling and Francine Clark remain the centerpiece, but the new and renovated buildings now conjure a broader artistic vision that links the art to the museum’s bucolic grounds, laced with hiking trails. 225 South St. 413-458-2303; clarkart.edu

BEST CONTEMPORARY ART MUSEUM MASSACHUSETTS MUSEUM OF CONTEMPORARY ART, North Adams

More than 100 large-scale wall drawings designed by artist Sol LeWitt are a must-see extravaganza of pattern and color at this bold museum that has transformed old brick mill buildings into a dynamic center for contemporary art. Leave time to explore the entire complex, where gigantic gallery spaces let artists unleash their creativity through often-fascinating installations. 1040 Mass MoCA Way. 413-662-2111; massmoca.org

BEST WATERFALL BASH BISH FALLS STATE PARK, Mount Washington

From the early-summer mountain laurel in bloom to the blazing colors of fall foliage, even the drive to this state park is a scenic delight. A woodsy trail leads to the falls, which plunge down a rocky gorge into a deep pool. The highest single-drop falls in the state even has its own tale of a Native American maiden in peril. Adjacent to Mt. Washington State Forest. Falls Road. 413-528-0330; mass.gov/eea

Perfect Weekend In The Berkshires
Bash Bish Falls State Park, Mount Washington
Photo Credit : Jerry and Marcy Monkman

BEST TREETOP ADVENTURE RAMBLEWILD, Lanesborough

Climb, walk, and zoom through the forest canopy on Ramblewild’s eight trails, each color-coded like a ski slope from yellow to double black diamond. The courses cover 17 acres with more than 100 elements—logs, nets, zip lines, rope bridges, ladders, tunnels—on a self-guided system with clip-in harness. All visits start with a short orientation for safety and technique. 110 Brodie Mountain Road. 844–iRAMBLE (844-472-6253); ramblewild.com

Perfect Weekend In The Berkshires
Ramblewild, Lanesborough
Photo Credit : Ramblewild

WHERE TO EAT

BEST BERKSHIRES BREAKFAST HAVEN CAFÉ & BAKERY, Lenox

Breakfast may be the most important meal of the day, and there’s no better place for it than this large and airy room where there’s always a buzz of happy diners. You can go elegant with a French-rolled omelet, sweet with croissant French toast, or hearty with an egg-and-cheese breakfast burrito. Breakfasts: from $7.50. 8 Franklin St. 413-637-8948; havencafebakery.com

BEST FARM-TO-TABLE DINING PRAIRIE WHALE, Great Barrington

Wunderkind restaurateur Mark Firth was thriving with farm-to-table restaurants in Brooklyn, but he decided to get much closer to the food sources and moved to the Berkshires. Now he raises Prairie Whale’s pigs, sheep, and laying hens in nearby Monterey and buys the restaurant produce locally. Start with fried green tomato and goat cheese, then savor roast chicken with baby turnips. Entrees: from $14. 178 Main St. 413-528-5050; facebook.com/PrairieWhale

BEST PICNIC FOOD NEJAIME’S WINE CELLARS, Lenox & Stockbridge

Whether you’re attending a concert at Tanglewood or taking a hike up Monument Mountain, this wine and gourmet shop takes all the work out of assembling a picnic. Choose the “French Country,” “Mediterranean,” or “Summer Classic” combo, or create your own spread of cheeses and specialty foods from the shelves and deli counter. Baskets: from $55 for two people. 60 Main St., Lenox. 413-637-2221. 3 Elm St., Stockbridge. 413-298-3454; nejaimeswine.com

BEST SMALL PLATES BRAVA, Lenox

Brava unites the best of Spanish and Italian small plates with exemplary selections of wine by the glass and beer on tap. Reservations aren’t accepted, but you can usually find a place at the bar to nibble on the likes of bruschetta with wild mushrooms, goat cheese, walnuts, and fig jam, or to tuck into a plate of lollipop lamb chops. Entrees: from $9. 27 Housatonic St. 413-637-9171; bravalenox.com

BEST TASTE OF THE ALPS THE HAFLINGER HAUS, Adams

The tavern, dining room, and outdoor beer garden at this Austrian inn feel like a taste of the Tyrolean Alps in the Berkshires. The schnitzels (pounded and breaded cutlets) are a treat, especially the jaeger (hunter) schnitzel with mushrooms, but don’t miss the goulash crêpe with paprika sauce, or the homey pot of goulash over handmade dumplings. Dining-room entrees: from $17.95. Tavern main dishes: from $9.95. 17 Commercial St. 413-743-2221; haflingerhaus.com

WHERE TO STAY

BEST SMALL-CITY BOUTIQUE HOTEL HOTEL ON NORTH, Pittsfield

This suave new hotel near the Barrington Stage Company brings contemporary comfort to a pair of handsome 1880s buildings. The 45 bedrooms, all a bit different, are decorated in low-key, soothing tones and furnished with pieces crafted by local artisans. Two rooms have working fireplaces and some have kitchenettes. Rates: from $159. 297 North St. 413-358-4741; hotelonnorth.com

Perfect Weekend In The Berkshires
Hotel on North, Pittsfield
Photo Credit : Martin Albert/Hotel on North

BEST MANSION GATEWAYS INN, Lenox

The 11 guestrooms in this 1912 mansion are named for Shakespearean characters, and the gracious lodging makes an elegant base for enjoying the summer arts scene. The piano bar is a good place for a quick pre-curtain dinner and a relaxing post-curtain dessert. Rates: from $180. 51 Walker St. 413-637-2532; gatewaysinn.com

BEST MOUNTAIN LODGING JIMINY PEAK MOUNTAIN RESORT COUNTRY INN, Hancock

Don’t let the “country inn” moniker fool you. These hotel suites, each with kitchenette, king-size bed, and queen-size sleeper, are contemporary ski-slope digs. The summer Adventure Park offers thrills and spills, but the pool and hot tubs might be enough for many travelers. Rates: from $125. 37 Corey Road. 413-738-5500; jiminypeak.com