Tastes of the Old Country Here

20 Things To Do In Woodstock, VT

It’s fall, and what is more quintessential New England than Woodstock, VT?  Here is a roundup of things to do in and around Woodstock. All personally tested and approved.



1. Morning Village Walk

Stroll through the village green, grab the morning paper at the Woodstock Pharmacy, enjoy a cappuccino at Mon Vert Cafe, wander back across the covered bridge, and see a breathtaking Vermont view from the center of the bridge.

2. Visit Farmhouse Pottery

The beautiful and inspiring Farmhouse Pottery is located in the old bible binding building, Owners Zoe & James create beautiful and functional pottery and more.

3. Simon Pearce: A True Vermont Experience

What can I say about Simon Pearce? The food was phenomenal. From the moment you enter the space, it’s warm and cozy but with a clean aesthetic that makes it feel crisp and chic. The restaurant takes great pride in offering local farm to table dishes.

Simon Pearce opened his glass blowing studio in 1981 and his wife Pia opened the cafe overlooking the Ottauquechee River two years later. It quickly gained recognition as one of the best in Vermont. Today you can still see glassblowing in action.

4. Long Trail: Follow the Trail to the Renowned Long Trail Brewery

Watch one of VTs best beer being made in front of your eyes then dine in the casual, rowdy restaurant and enjoy the tastes of all the different brews on offer. Hike Killington, sit by the river by the river and enjoy a pint.

5. The Famers Market

Near 506 on the River, there is a hugely popular and world-class farmers market. A wonderful selection of sandwiches, prepared food, and baked goods are available. It features some of Vermont’s best cheeses on display. Grab some cheddah and MacIntosh apples and you have a great snack.

6. Hike Suicide Six

Stop by Teago General Store on the way to see Grandpa Chuck, get a great sandwich, hot chocolate and a taste for the local goings-on in Pomfret. Suicide Six is is also a great afternoon summer hike or ski in the winter.

7. Time to Feed the Cows

Billings Farm and Museum gives visitors a glimpse into history and of farming life in Vermont. Animals, wagon rides and event throughout the year make it a special stop for kids.

8. Market on The Green

Every Thursday, visit the Village Green for a selection of fresh produce, prepared food, crafts and live music.

9. Sugarbush Farm

A living, thriving Vermont Farm as it should be. Sample cheeses, learn how to make maple syrup and experience agricultural heritage in action.

10. Bentley’s Restaurant

In the heart of downtown Woodstock, Bentley’s serves great steaks and burgers, alongside late-night weekend dancing and music. This is the spot to get your groove on.  From 5 pm – 7 pm you’ll find locals and shop owners enjoying an evening cocktail.

11. Gillingham’s

Woodstock’s oldest store – operating since 1858. Step back in time to an authentic general store with a modern twist and a great variety of Vermont products, crafts, and gifts.

12. The Mansion and Gardens National Historic Park

Enjoy the architecture and grounds of this beautifully preserved mansion. Bring a picnic and stay for the scenery.

13. The Village Butcher

George makes the best sandwiches downtown. Pick one up then enjoy it at the Historical Society. The extensive back lawn is open to the public and offers beautiful views of the Ottauquechee River.

14. Cloudland Farm

A wonderful farm-raised dinner awaits in a magical setting. Advance bookings required.

15. Mount Tom: 30-40 Minute Hike to the Top

Bring packed lunch and enjoy beautiful views of Woodstock Village.

16. The Woodstock Historical Society

A must for any yesteryear fan with a unique insight into the history of Woodstock and the area. Stories and photos of the creation of Woodstock are on display, as are the recollections of famous and not-so-famous people who lived and visited this special town over years gone by.

17. Town Supper

Organized by the community in various granges and town halls across the state. Town suppers are a New England tradition and a wonderful experience of community and delicious home cooked food.

18. Explore Queeche Gorge

An easy hike, Queeche Gorge has breathtaking views and is only 15 minutes from Woodstock Center.

19. Barnard Lake Swim and Lunch at the Barnard Store

This is splendid with a great full-day bike ride on the back Stage Road.

20. Woodstock Country Club

Round of golf or a winter cross country ski at the Robert Trent Jones designed Woodstock Country Club.

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