The Ultimate Guide to Woodstock, VermontIt doesn't get more Vermont than Woodstock. And I can say that as I grew up in this state and have been to almost every town. Woodstock is historic, charming and a flashback to another era. Yet it still has great dining, fun things to do for couples and families, and it still is authentically VT.Authorskelleyferro
DestinationsWoodstockItinerary

Where to Stay

Woodstock Inn & Resort
The iconic resort that is synonymous with Woodstock, "the Inn" as locals refer to it, is the heart of the town and it's centrally located off the main street and Green. Majestic in all seasons, this historic hotel has updated rooms that keep that Vermont charm. With an affiliated health & raquet club, an onsite pool, golf, a nearby ski area and a farm, the Inn is the perfect bouncing off point to explore Woodstock.
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Where to Dine

Cloudland Farm
Such a special experience, make sure to check out Cloudland Farm just outside of town. Set on a real working farm, the nightly menu features the food grown right on their land. From their own chickens, to fresh vegetables from their garden to their own hand raised meats--it doesn't get more farm to table than this. The setting is lovely in a farmhouse with a fireplace. Tip: It is also BYOB so don't forget to bring a bottle of wine!
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Mon Vert Cafe
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Village Butcher Shop
Upscale meats, cheeses and wines can be found here and will make excellent picnic fare. Don't miss their sandwiches on homemade breads. Pricey but delicious!
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Simon Pearce
For a special night, Simon Pearce's restaurant is set on the very top of a waterfall, next to their covered bridge. Famed for their handmade glassware, the restaurant uses all their pottery and glass, and the food is elegant and delicious--with signature dishes and daily specials that keep locals coming back. Tip: White Chocolate Mousse cake. Wow.
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The Prince & The Pauper Restaurant
Tucked away in a little corner, this very romantic and dimly lit restaurant has been popular for decades and for good reason. Cocktails, homemade breads and well crafted plates make this a classic little bistro spot. Tip: not the best for families but come for a date night
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Woodstock Scoops
Homemade ice cream and all the toppings--we love Scoops for it's quality ingredients. Their Maple Ice Cream uses local organic maple syrup from a nearby farm! Tip: the Maple Creemee is a Vermont classic
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Fun Things to Do

Saskadena Six
Small but mighty, we love this ski area just 15 minutes from the village center. It's two lifts (3 if you count the bunny slope) makes it manageable yet there's a variety of terrain. It's perfect for littles learning to ski and for friends that want to have a fun day on the slopes without the hassles of the big mountains. Tip: The classic ski lodge is so charming--grab a beer and sit by the fireplace or the outdoor fire pit!
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Sugarbush Farm
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Billings Farm & Museum
A working farm and museum, Billings is a MUST stop. The history about the farm, the Rockefeller's that lived in town and their farming practices are very interesting. A highlight is their cow barns, where you can take a free tour and learn about their beautiful herds and pet baby cows. In the warmer months, you can walk the farm and see the chickens, horses and goats. Tip: They make their own ice cream at their ice cream shop using their own milk--heaven!
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Local Landmarks

Middle Covered Bridge
The most photographed spot in town, and for good reason, this classic covered bridge is the icon of Woodstock. Take your photo then walk over it and enjoy the view of the Ottauquechee River.
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Norman Williams Public Library
An interesting, classic library with a wonderful kids area, filled with games, building tables and offering many story times. Tip: Great spot for littles, especially on chilly days!
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Mount Tom
The town's central hilltop that is adorned with a star year round, Mount Tom is a perfect hike. An easy to moderate climb on a well maintained trail will get you to the top for a well worth it view of the town and the whole valley. Tip: Pack a picnic from the Village Butcher and enjoy at the top!
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Where to Drink

Abracadabra Coffee Co.
This spot has developed a cult following for it's amazing espresso drinks, cool vibe and tasty pastries. Grab a tshirt along with your order.
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Au Comptoir
You'd never guess that behind the main street, off of a parking lot, there's a tiny little building that is home to a perfect little cocktail bar. Expertly mixed drinks and snacks, this bar is sophisticated yet approachable. The outdoor seating is lovely -- and kid friendly!
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Favorite Shops

F. H. Gillingham & Sons
The oldest shop in town, Gillinghams has everything. A little bit general store, grocery store, gift store, toy store and everything in between. Still owned by the Gillingham's, we love to support this beacon of Woodstock.
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N.T. Ferro Jewelers
A staple for the past 25 years, this jewelry shop is also part of the lifeblood of the town. A husband & wife team owns the shop and welcome all in. They create custom pieces, memorable Woodstock charms and have one of kind estate finds. Tip: Mention me as this is my parents' shop. Maybe you'll get a deal. ;)
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Woodstock Farmers' Market
Another town meeting spot, the Farmer's Market is actually an upscale grocery store and deli counter, that serves great sandwiches, top of the line meats/fish/prepared goods and coffee. You'll find a lot to love in this market.
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Woody’s Mercantile
For timeless souveniers that are good quality, Woody's is the stop. Buy your friends something here -- and yourself! There's a lot of functional and fun items.
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