Brattleboro’s unofficial meeting hall is Amy’s Bakery Arts Cafe (113 Main St., 802/251-1071, 8 a.m.–6 p.m. Mon.–Sat.; 8 a.m.–5 p.m. Sun., $6.50–10), where locals catch up over fresh-baked bread, pastries, and coffee at tables overlooking the Connecticut River.

A closer eye on the water can be had at the Riverview Café (36 Bridge St., 802/254-9841, www.riverviewcafe.com, 7:30 a.m.–9 p.m. daily in spring, summer, and fall; in winter open 7:30 a.m.–9 p.m. Sat. and Sun., 7:30 a.m.–3 p.m. Mon.–Fri., $15–20), where kayakers and blue herons sometimes join diners at river-level. The menu of sandwiches, pasta, and grilled entrées emphasizes fresh ingredients from local farms.

The best meal in town—and one of the best in Vermont—can be found at T. J. Buckley’s Uptown (132 Elliot St., 802/257-4922, 6 p.m.–9 p.m. Wed.–Sun., $3035 prix fixe, cash or check only), a renovated 1927 Worcester diner car with an open kitchen and just five tables. Chef-owner Michael Fuller prepares a handful of options in a small open kitchen each night. All of them feature bold flavor combinations, such as venison with eggplant caponata, truffle oil, and fresh currants; and melt-in-your-mouth quail with duck leg confit and root vegetables.

Another great bet is Adagio Trattoria (123 Main St., Brattleboro, 802/254-6046, www.adagiotrattoria.com, 5 p.m.–10 p.m. Mon.–Wed.; 11:30 a.m.–3 p.m. and 5 p.m.–10 p.m. Sun.; 11:30 a.m.–3 p.m. and 5 p.m.–10 p.m. Thurs.–Sun., $21–30) whose fans regard Chef Eric Craw as a quasi-rock star for his creamy pastas (the Bolognese is a standout), and fresh and creative antipasti and salads. His “deconstructed tiramisu” is a sight-and taste-to behold.