Woodstock is a small village in the hills of central Vermont, on the Ottauquechee River, with an oval green, white steeples, Federal and Greek Revival homes and three covered bridges nearby. It has looked much the same for two centuries, and in December its streets glow with candles in windows and lights on the old homes. On Wassail Weekend in mid-December, horses parade around the green. The first day stays on foot in the village.
The village green
Where to eat: Coffee and a scone at Mon Vert Cafe on Central Street.
Start on the oval village green, ringed by old homes, the Windsor County Courthouse and the Norman Williams Public Library, a stone building from 1884. Walk the loop slowly and look at the details on the houses, the fanlights and the black shutters. In December the green holds a tall lit tree, and on Wassail Weekend it fills with an artisan market, a bonfire and carolers.
The Middle Covered Bridge
Walk a block to the Middle Covered Bridge over the Ottauquechee River, a wooden bridge rebuilt in 1969 by hand using old methods. Walk through it and look at the timber trusses inside, then stand on the riverbank for the classic view of the bridge with the steeples behind. In winter, ice forms on the rocks below and the river runs dark and quiet.
F.H. Gillingham and Sons
Where to eat: Sandwiches and a cup of soup at Mon Vert Cafe.
Wander the shops along Central and Elm streets, then step into F.H. Gillingham and Sons, a general store run by the same family since 1886. The wooden floors creak, and the shelves hold Vermont cheddar, maple syrup, hardware, wool socks and penny candy. Pick up a small bottle of syrup or a block of aged cheddar to take home. Nearby, galleries and bookshops fill the old brick storefronts.
Candlelight and dinner
Where to eat: Rack of lamb at The Prince and the Pauper.
As the sun sets around half past four, the village windows glow with candles and white lights. Walk the quiet side streets, such as Elm Street and the Pleasant Street homes, and see the old houses lit for the season. Then settle in for a long dinner, by a fire if you can, at one of the village's small restaurants. Woodstock is calm after dark, good for an unhurried evening.
Where to eat and stop
- Breakfast · Mon Vert Cafe — Central Street Why here: A bright cafe in the center of the village.
- Lunch · Mon Vert Cafe — Central Street Why here: Local cheddar and a warm cup on a cold day.
- Dinner · The Prince and the Pauper — Elm Street Why here: A candlelit dining room in an old building.
- Quick stop (treat): F.H. Gillingham and Sons — Elm Street Why here: Local treats from a family general store since 1886.
Woodstock is about two and a half hours from Boston and about two hours from Burlington by car. Park once near the green and walk the village, the covered bridge and the shops.
Where to stay
- An inn on or near the village green — Historic inns and bed and breakfasts face the oval village green or sit a block away, walkable to the covered bridge, the shops and dinner, many with fireplaces.
- A bed and breakfast in the hills — Farmhouse bed and breakfasts on the back roads around Woodstock and Pomfret offer quiet rooms, mountain views and big breakfasts, a short drive from the village.
Dinner: Rack of lamb at The Prince and the Pauper on Elm Street.
Tomorrow: Visit Billings Farm and Museum, walk the carriage roads of Marsh-Billings-Rockefeller National Historical Park and taste cheese and maple at Sugarbush Farm.
Bad-weather plan
On a rainy or snowy day, spend longer in the library, the general store and galleries, then warm up with soup by a cafe window.
Village green · Middle Covered Bridge · General store · Candlelight
Good to know: Sidewalks can be icy in December; wear boots with good grip and take care on the stone steps by the river.
