For restless city-dwellers, driving into Dorset is like entering a Thornton Wilder scene—the perfect example of what urbanites forfeit in favor of skyscrapers and dim sum. Lined with clapboard homes and divided by a town green, Church Street is home to the requisite general store (complete with ’70s-era gas pump) and several gracious inns where days are dominated by pancakes and porch-sitting. But the town is more than a relic: In addition to penny candy, its store has a gourmet deli and a separate wine room. Perhaps that’s why there’s no mass exodus here during mud season; even the summer people come up year-round. —Brigid Sweeney

WHERE TO EAT, STAY, AND PLAY 

New England’s Best Small Towns 

Photo by Jesse Burke