How to Have the Perfect Family Vacation in the Berkshires
In the Berkshires, the easy days of summer—swimming holes, berry patches, meandering hikes through farmland and forests—meet world-class museums and culture festivals in one fantastic, make-everyone-happy family vacation.
Great Barrington & Stockbridge
After your dose of high art, these historic towns offer more low-key culture. Start at Stockbridge’s Norman Rockwell Museum; this summer’s event “Mom, Apple Pie, and Rockwell’s Models” is a celebration of the simple pleasures that inspired the artist, with music, classic American fare, and the chance to meet some of his models (413-298-4100).
STAY
The history lessons continue at the Red Lion Inn in Stockbridge. Dating from 1773, it has period furnishings and a wide porch with rocking chairs (30 Main St.; 413-298-5545; doubles from $155).
Williamstown & North Adams
From here, it’s a few miles east to North Adams and MASS MoCA. Stop by the contemporary art hub’s dedicated Kidspace, which has installations by Anselm Kiefer and colorful wall drawings by Sol LeWitt (413-662-2111). Nearly an acre of interior walls were built at MASS MoCA to showcase LeWitt’s large-scale drawings.
STAY
After a day of exploring, retreat to the Porches Inn at MASS MoCA, a series of Victorian row houses with oversized rooms and suites that work particularly well for families (231 River St.; 413-664-0400; doubles from $190). The pool is a big plus on hot summer days, as are the breakfasts, which are delivered to your door in traditional millworkers’ lunch boxes. There’s also the Guest House at Field Farm, a Williamstown B&B with a mid-century modern aesthetic and an impressive contemporary art collection. It’s on 300-plus acres of conservation land, with guided walks for children in summer (554 Sloan Rd.; 413-458-3135; doubles from $200).
Lenox & Becket
Summer is high season for the performing arts here. Tanglewood, home of the Boston Symphony Orchestra in July and August, premieres on July 5 in Lenox, south of Williamstown. Pack a picnic, sit on the lawn, and listen to performers like Joshua Bell, Yo-Yo Ma, and James Taylor. The Afternoon Family Concerts and the Boston Pops’ rendition of _The Wizard of Oz _are lively and informal, with children roaming (relatively) free on the lawns, even during concerts (888-266-1200).
PLAY
There’s always something inspiring to see at the Jacob’s Pillow Dance Festival in Becket, where free outdoor performances Wednesday through Saturday evenings—more than 40 throughout the season—offer a distinguished lineup of contemporary dance and ballet (413-243-0745). Shakespeare & Company’s summer production of _Romeo and Juliet _at The Mount—Edith Wharton’s majestic former estate, pictured here—gives young theatergoers an introduction to the playwright, while scavenger hunts keep the little ones busy in maze-like gardens (413-551-5111).
Lenox & Becket
Even in an area with no shortage of great lodgings and restaurants, Wheatleigh—a spectacular 19th-century Florentine-inspired palazzo in Lenox—stands out as one of the most luxurious. Parents can relax in a neutral-hued suite or by the pool while children explore the endless lawns (11 W. Hawthorne Rd.; 413-637-0610; doubles from $715). Stonover Farm, a B&B also in Lenox, has two stand-alone villas—the two-bedroom Rock Cottage and the 600-square-foot School House—for families craving a little extra space (169 Under Mountain Rd.; 413-637-9100; doubles from $335). Just up the road, the stately Blantyre is another excellent option; kids will love the turrets, gargoyles, and other castle-like ornamentation, as well as games like boccie, shuffleboard, and croquet. There’s also a superlative spa for adults (16 Blantyre Rd.; 413-637-3556; doubles from $600).
Lenox & Becket
Regardless of where you stay, stop at a roadside stand for fresh produce, then breakfast burritos and granola at the Haven Cafe and Bakery in Lenox (8 Franklin St.; 413-637-8948). And be sure to have dinner at Becket’s Dream Away Lodge, a farmhouse where the food, including the delicious duck carnitas tacos, is as magical as the atmosphere; there’s also live music and bonfires nightly (1342 County Rd.; 413-623-8725; entrées from $20).
Williamstown & North Adams
A quintessential college town complete with church spires and a postcard-worthy main street, Williamstown (home of Williams College) would merit a stop even if it weren’t the site of the new Tadao Ando–designed Clark Art Institute, which opens on the Fourth of July. Families can fill an entire afternoon and evening on some days with everything from outdoor concerts to the stellar collection of Impressionist art, as well as the interactive Looking Carefully Cards for kids six and up, which turn gallery gazing into an act of discovery (413-458-2303). For your naturalists-in-training, head to Cricket Creek Farm, a working Williamstown dairy and bakery where they’ll learn about caring for farm animals and making cheese (1255 Oblong Rd.; 413-458-5888). Or you can spend an afternoon watching dragonflies flit and red-tailed hawks soar at Mountain Meadow Preserve, 180 pastoral acres with miles of easy trails just up the road from Williamstown (413-298-3239).
Great Barrington & Stockbridge
Also in Stockbridge, the Berkshire Botanical Garden (pictured)—with its free Family Fridays featuring birds of prey and the snakes of Berkshire County, a hut made of willow, and a Hogwarts-inspired herb garden full of wacky-looking plants—shouldn’t be missed (413-298-3926). Nor should the nearby Naumkeag, an eccentric Gilded Age estate with eight acres of terraced gardens (413-298-3239).
Great Barrington & Stockbridge
Cooling off at Bash Bish Falls State Park, home to the area’s highest single-drop waterfall and a short drive from Great Barrington.
Great Barrington & Stockbridge
For another outdoor excursion, visit Otis Reservoir (pictured), outside Great Barrington, or Sheffield’s Bartholomew’s Cobble, the only National Natural Landmark in the Berkshires, with massive limestone and marble outcroppings created by ancient geologic shifts (413-229-8600).
Great Barrington & Stockbridge
Picking berries is a rite of summer in the Berkshires, with blueberry season kicking off at Great Barrington’s Windy Hill Farm on or around the Fourth of July (413-298-3217). Nearby, Noble’s Tweenbrook Farm has strawberries (356 E. New Lenox Rd.; 413-443-2210) and Bartlett’s Orchard, in Richmond, offers late-summer apple picking (413-698-2559).
EAT
In Great Barrington, the French-inflected Bizalion’s is known for its simple menu of crusty baguettes filled with prosciutto, Gruyère, and sweet cornichons (684 Main St.; 413-644-9988; sandwiches from $8). For an early dinner of _shumai _and soba, go to **Bizen Kaiseki **(17 Railroad St.; 413-528-4343; entrées from $7). End the evening the way all good summer evenings should: with ice cream. You can’t go wrong with a scoop of mint chip or mission fig from SoCo Creamery (955 S. Main St.; 413-528-8400).