Perfect Weekend in Woodstock, Vermont

From shopping to dining to cozy overnight stays, this small town has oversize appeal.

By Yankee Magazine

May 30 2017

043_VT Chamber of Commerce.

Woodstock, Vermont

Photo Credit : courtesy of Vermont Chamber of Commerce
Woodstock, Vermont
Woodstock, Vermont
Photo Credit : courtesy of Vermont Chamber of Commerce

If you’re looking for the quintessential New England village experience, add Woodstock, Vermont, to your itinerary. Here you’ll find one of the Northeast’s most photographed covered bridges, a town green bounded by beautiful homes, and one of Yankee’s favorite places to stay, the Woodstock Inn, as well as F.H. Gillingham & Sons, a sprawling general store that first opened its doors in 1886.

Ready for a visit? Read on to discover a selection of Yankee editors’ picks for Woodstock.


Billings Farm and Museum Frederick Billings’s model farm, established by the railroad magnate when he returned to his native Woodstock in 1871, still showcases champion Jersey cows, Southdown sheep, and magnificent draft horses. Visit the 1890 farm manager’s home and creamery, learn about farm work of yesteryear and today, and climb aboard for horse-drawn wagon and sleigh rides. Interactive farm programs change with the seasons. 69 Old River Road. 802-457-2355;

Sugarbush Farm For more than 70 years, this small family farm has been crafting tasty cheeses and maple syrup. Sample the wares, visit the animals, and tour a traditional low-tech sugarhouse. 591 Sugarbush Farm Road. 802-457-1757;

F.H. Gillingham & Sons You could spend an hour or an entire afternoon at this sprawling and entertaining general store, one of Vermont’s oldest and certainly most celebrated shops of its kind. What will you find? Oh, just about everything, most of it Vermont-centric, from postcards and maple products to clothing and local cheeses. In true Vermont fashion, Gillingham’s is still family owned, and now run by the founder’s great-grandsons, Frank and Jireh Billings. 16 Elm St. 802-457-2100.


506 On the River Inn Just a few miles from the center of Woodstock, along the scenic Ottauquechee River, thistwo-year-old property combines the best features of a small resort with those of an intimate inn. At guests’ disposal are river-facing rooms and suites with balconies and rocking chairs, an antiques-filled bistro and bar, a game area for young adults, a toddler playroom, an indoor pool and sauna, and a sweeping lawn dotted with lounge chairs, tiki lamps, and fire pits for evening s’mores. 1653 W. Woodstock Road (Rte. 4). 802-457-5000;

Woodstock Inn & Resort Crossing the threshold at Woodstock’s best address is like stepping into a sumptuous country home. Many guest rooms feature wood-burning fireplaces; all are distinctively furnished. Local ingredients enrich the menus at the Red Rooster, the inn’s light-filled main dining room, and at the snug, wood-paneled Richardson’s Tavern. The resort offers golf, ski, and spa packages, plus activities ranging from fly-fishing to falconry. Woodstock’s shops, restaurants, and town green are at the inn’s doorstep. 14 The Green. 802-332-6853;

The Jackson House Inn Romance is the hallmark of this luxury inn, from its elegant English gardens to the imaginative two-course breakfasts. Rates include full breakfast. 43 Senior Lane. 800-448-1890;


Mountain Creamery Upstairs in the restaurant, have a slice of “mile-high” apple pie with a scoop of the creamery’s vanilla. Downstairs in the ice cream shop, enjoy a homemade waffle cone with great flavors such as Myers rum raisin, Vermont maple walnut, and brownie à la mode. 33 Central St. 802-457-1715;

Melaza Bistro Woodstock meets the islands. The Puerto Rico–born chef at this cheery little spot serves up empanadas, plantain chips, and entrées such as mussels in Cuban creole sauce, jerk mahi-mahi, and pork shank with guava glaze. Rum, naturally, rules the cocktail lineup. Outdoor seating is available. 71 Central St. 802-457-7110;