Almost ridiculously pretty, this little village in east-central Vermont was established in 1761 by settlers from Massachusetts. Thanks to the devotion of the residents to the town’s architectural heritage, gracious 18th- and 19th-century buildings remain, handsome as ever. Among them: F.H. Gillingham & Sons, the town’s general store since 1886 and still the go-to spot for hardware, housewares, food, produce, and things with the “made in Vermont” pedigree. Much of the village is listed on the National Registry of Historic Places.
The best way to get a feel for the town is to stroll along Elm and Central streets, browse the shops and galleries, and walk across the covered bridge that spans the Ottauquechee River. Woodstock’s centerpiece, the village green, is ringed with buildings of different styles, from Federal mansions to a Greek-Revival courthouse and a Romanesque-style library. It’s all quite charming, and feels like a trip to the past, until it comes time to pay the bill. But you’ll leave loving Woodstock in spite of that.