It’s got a cheesemonger, an old-time general store, and a new-age co-op market within a four-street radius. Yet the real allure of Great Barrington is Railroad Street, a single block with enough culinary delights to fill a weekend visit from beginning to end.

Friday dinner: Far-flung entrées (Himalayan antelope loin, Australian lamb) and a tasty bar menu elevate Pearl’s above the average surf-and-turf shop [EDITOR'S NOTE: Pearl's closed indefinitely after the October issue went to press].

Saturday breakfast: Locals hit Martin’s early—as in, 6 a.m.—for hefty omelets with a side of town gossip. Tourists take the second shift and scarf bagels piled with smoked salmon and cream cheese.

Saturday lunch: The Yo-Yo Ma roll (bigeye tuna, avocado, mango, multicolored roe) at sushi bar Bizen makes fighting for a seat—or spending $100 on lunch—an acceptable tradeoff.

Saturday dinner: Get your fill of local flavor at Allium, where chef Michael Pancheri rewrites the menu daily after making the rounds of area farms.

Sunday brunch: Line up at 11:30 a.m. at 20 Railroad Street for juicy Kobe, Angus, and bison burgers, and to people-watch out the wide, street-facing windows.

Sunday pre-drive snack: Busy "micro-creamery" SoCo scoops gelato, sorbet, and ice cream in flavors like snickerdoodle caramel crunch and peanut butter mudslide. —Sascha de Gersdorff

WHERE TO EAT, STAY, AND PLAY 

New England’s Best Small Towns 

 Photo by Keller + Keller