Great Fall Getaways

ALL TOO OFTEN, a weekend trip works for precisely half your group. While some get the escape of their dreams (Let’s hit the whitewater rapids! Time to explore the cheese trail!), others wind up merely tagging along for the ride. This fall, why sell anyone short? Head to one of these 10 versatile New England destinations, all teeming with quirky fun and just three and a half hours or less from Boston. Whether your crew includes thrill seekers, gastronomes, spa junkies, or even art, history, and antiques aficionados, your ideal retreat awaits. Steal these itineraries, and consider the crowd pleased.

Stowe, Vermont

Litchfield Hills, Connecticut

The Pioneer Valley, Massachusetts

Penobscot, Maine

Portland, Maine

Nantucket, Massachusetts 

Provincetown, Massachusetts 

Newport, Rhode Island

Woodstock, Vermont

Portsmouth, New Hampshire


Plus: only online, 10 more reasons to visit each of these locations and enjoy the coming of fall with a pig-racing, oyster-shucking, hair-standing, boat-rocking, heck-of-a-good time.


Contributors: Donna Garlough, Brittany Jasnoff, Naomi Kooker, Janelle Nanos, Rachel Slade.
Photographs by Christopher Churchill, unless otherwise noted.


  • Sarah

    Only ONE suggestion for NH? Where’s the love? I mean…the White Mountains are the PERFECT fall getaway!