The food may be fresh, but the ambience at Bentley’s Restaurant (3 Elm St., 802/457-3232, www.bentleysrestaurant.com, 11:30 a.m.–9:30 p.m. daily, $10–27) is charmingly (and authentically) old. The casual gleaming bar brims with tassled lamps, velvet couches, palm fronds, and brocade bar stools, while the kitchen churns out hearty comfort foods like maple mustard chicken and linguine with seafood.

Sedate and sophisticated, Prince & The Pauper (24 Elm St., 802/457-1818, www.princeandpauper.com, 6 a.m.–9 p.m. daily, $18–48) serves high-concept cosmopolitan dishes (don’t miss the restaurant’s signature Carre d’Agneau Royale) in a candlelit country setting—think high-backed wooden booths, exposed beams, and local art for sale on the wall. It’s an ideal date setting, though it also successfully caters to families and groups.

Meanwhile, a bit of sophisticated city comes to the country at the beautifully designed Red Rooster (14 The Green, Woodstock, 802/457-1100 or 800/448-7900, www.woodstockinn.com, 12 p.m.–10 p.m. daily). A new addition to The Woodstock Inn, the high-energy but comfortable space centers on a pretty water pool, around which couples and families alike dig into a New American menu of oysters on the half shell to coq au vin and braised short ribs.

Break out the dry cleaning for breakfast and lunch at The Main Dining Room (14 The Green, 800/448-7900, www.woodstockinn.com, $24–35) at the Woodstock Inn. The subtly grand space is where to find lovelies such as scallops with truffle vinaigrette followed by Grand Marnier soufflé glacé—not to mention a flat-out scrumptious (and epic) Sunday brunch.