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.
Facing the village green, the AAA-four-diamond-rated Woodstock Inn & Resort (14 The Green, 800-449-7900, www.woodstockinn.com, $260 and up) is a local landmark, originally opened in 1892 and purchased by Laurance S. Rockefeller in 1969. A short walk to shops, galleries, and restaurants, the inn is a destination itself, with a spa, restaurants, indoor and outdoor tennis, and the only golf course in Vermont designed by Robert Trent Jones Sr. Rooms vary in size and shape, but all are luxuriously turned out with handmade quilts and sun porches. As seen in a famous Budweiser holiday commercial, the Kedron Valley Inn (4778 South Road, South Woodstock, 802-457-1453, www.kedronvalleyinn.com, $259 and up) is a circa 1828 property set on 11 acres. The 25 guest rooms are divided among the main inn, a tavern building, and an Adirondack-style log lodge (coolest digs, with exposed log walls and fireplaces). The Jackson House bed-and-breakfast (43 Senior Lane, 802-457-2065, www.jacksonhouse.com, rooms from $185) cossets guests with Frette linens and robes and Anichini coverlets, and wins their hearts with luscious breakfasts (think organic maple yogurt with pumpkin butter and homemade granola, or almond-pear brioche). The decor is different in each of the six suites and five guest rooms, ranging from Vermont country to Victorian. Mush alert: The garden maze was voted “best place to kiss in Vermont.”
Confession: We’d drive to east-central Vermont if only for the fabulous sandwiches at the Woodstock Farmers’ Market (979 West Woodstock Road, 802-457-3658, $9-$25). Among the 26 specialty sandwiches is a turkey number that features local cheddar, Granny Smith apples, thickly-sliced roasted turkey, and grainy mustard on fresh sourdough bread. They sell prepared foods, killer desserts, and gourmet snacks, too, but really, it’s all about the sandwich. Tucked away off an alley, The Prince & The Pauper bistro (24 Elm St., 802-457-1818, www.princeandpauper.com, $13-$30) offers seasonal, French-inspired cuisine in an informal atmosphere. Chef-owner Chris Baker has been winning raves from everyone (including Bon Appetit) for 25 years, thanks to his winning ways with lobster bisque, seafood crepes, grilled duck breast, and other house specialties. It takes some doing to get to Cloudland Farm (1101 Cloudland Road, 802-457-2599, www.cloudlandfarm.com) — you’ll drive down a 4-mile-long dirt road to the farm, open Thursday and Saturday nights only, but dinner here is an event. The farm-to-table menu is revealed on the website on Tuesday or Wednesday (plan to pay $43-$45 per person for the three-course menu on Saturday, and $30 per person for the two-course supper on Thursday). The menu tells you where every item on your plate came from, including the meat (sourced on site — now that’s local). An unexpected find on Central Street is Melaza Bistro (71 Central St., 802-457-7110, www.melazabistro.com, $5-$24), a mojitos-and-tapas joint. Caribbean and New England merge happily on the plate; good choices include jerk mahi mahi and chicken allimon.
Plan to spend a couple of hours at Billings Farm and Museum (River Road, 802-457-2355, www.billingsfarm.org, $12), a working dairy farm founded in 1871, one of the oldest in the country. Still operating, the farm offers interpretive tours of a restored 1890 farmhouse and daily demonstrations of butter-making in a basement creamery. Located across the street from the farm, the Marsh-Billings-Rockefeller National Historic Park (54 Elm St., 802-457-3368, www.nps.gov/mabi, $8 mansion and garden tour) is an art-filled Queen Anne mansion that reflects the conservation efforts of three of its residents, author-environmentalist George Perkins Marsh, Frederick Billings (founder of Billings Farm), and Mary French Rockefeller, who, with husband Laurance, sustained the farm and property from the mid- to late-20th century. Check out the interesting selection of shops in the village, including uber general store F.H. Gillingham & Sons (16 Elm St.) and vintage fashion boutique Who Is Sylvia? (26 Central St.). For a real walk, hike to the summit of Mount Tom, close to the heart of Woodstock. With a vertical rise of 600 feet, this is a lovely hike for minimal effort through woodlands of mixed hardwoods and evergreens (some 80 to 100 years old), festooned with wild ginger, trillium, and jack-in-the-pulpit in springtime. Switchbacks wind to the top of the mountain, past a small pond called The Pogue, with nice views of the village and beyond.
You won’t find a club scene in this quaint little village, but you might hit on a musical or stage performance or a first-run movie at Pentangle Arts Council (Woodstock Town Hall Theatre, 31 The Green, 802-457-3981, www.pentanglearts.org). For a nightcap or a booty-shake, hit the recently-reopened Bentleys (3 Elm St., 802-457-3232, www.bentleysofwoodstock.com). For something fun and different, take a baking class at King Arthur Baking Co. (135 US Route 55, Norwich, 802-649-3361, www.kingarthurflour.com, prices vary). It offers several evening sessions, even classes in gluten-free and sugar-free baking.
Woodstock is 140 miles northwest of Boston. For information, visit www.woodstockvt.com.