Massachusetts Trips – New England Weekend Getaways

Contrary to the unfortunate catchall “Masshole” (owing to their unique driving etiquette), Bay Staters are a multifaceted bunch. Over the years they’ve earned reputations for snootiness (Boston Brahmins), intellectualism (Harvard, Williams grads), ambition (John Kerry, Mitt Romney), and fierce loyalty (Red Sox Nation)—yet they possess subtler, more affable qualities, too. In fact, most locals balance the above with warmth and thoughtfulness, embracing outsiders and new ideas (gay marriage, legal marijuana) with measured rationalism.

The complex native character is matched by a state diverse with man-made and natural wonders. Boston, with its historic brownstones, lively North End, and Charles River, is the most European of American cities. Some 120 miles west, the Berkshire Hills—emerald in summer, burnt orange in fall—are peppered with lakes, mountains, and endless cultural offerings. Between the two are miles of farmland, steepled New England villages, and up-and-coming towns like Northampton. To the east, Cape Cod and the Islands draw families, outdoors enthusiasts, and plenty of A-list jet-setters. Summer is the high season here: Plan ahead, and save luggage room for new books, antiques, and all that Harvard paraphernalia.

[sidebar]Navigator: The Berkshires
Once a playground for tony Manhattanites and Boston Brahmins, the (now slightly more democratized) Berkshires are a mélange of cultural, culinary, and open-air attractions. Natives avoid the masses by frequenting these less well-known gems.

New England’s Best Small Towns: Great Barrington, MA
Because… it’s home to the Berkshires’ own Restaurant Row.

New England’s Best Small Towns: Harvard, MA
Because… the pickings are prime. Enough apple orchards to make Johnny Appleseed dance a jig. 

New England’s Best Small Towns: Shelburne Falls, MA
Because… if you can imagine it, they can make it. Few places are more antichain than Shelburne Falls, where everything—and we mean everything—is handmade.

Summer Escapes! 2009: The Great(est) Lakes: Long Pond
The 6.4 miles of pine-shaded shoreline spans the towns of Brewster and Harwich, for anyone requiring a quick social fix.

All in the Family: Ocean Edge Resort vs. Chatham Bars Inn vs. Wequassett Resort
With twin toddlers in tow, JULIE SURATT heads to three Cape resorts to see just how well they accommodate harried parents (and their cranky offspring).

Navigator: Boston Harbor Islands
Just a 15-minute, $14 ferry ride from downtown Boston, the Harbor Islands are a sweet respite from city congestion.

Boston’s Finest
Boston magazine’s savvy editors reveal their favorite city haunts—so you can skip the guidebook and hit the streets.

Ask a Native: Nancy Walls
A former Daily Show correspondent, the Cohasset-born comedienne specializes in hilarious bit parts (The Office and The 40-Year-Old Virgin). But she and husband Steve Carell are dead serious when it comes to hometown pride.

A Weekend In: Northampton
Just two hours from Boston, collegiate Northampton (that’s “Noho” to you) has blossomed into a hot spot for free spirits and food lovers.

Road Warriors
Part athletic challenge, part exercise in togetherness, an 80-mile bike ride takes a couple to the brink—of Cape Cod. Plan your own trip!

Taste of the State
Our top culinary delight in Massachusetts. Bowled Over.