Great Fall Getaways

Edited by Courtney Hollands


Photograph by Christopher Churchill

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


Contributors: Donna Garlough, Brittany Jasnoff, Naomi Kooker, Janelle Nanos, Rachel Slade.