So many things to do
in Woodstock, Vermont!
We wanted to get out of the city for a weekend getaway, and finding this lovely B&B made our trip to Woodstock and Vermont so perfect! We went on a mini snowy-hike/walk through Faulkner Park towards Mt Tom for views of the town. The B&B is walking distance from the trail and town center, which was perfect.
Woodstock is truly a four-season destination, with things to do all year round. While outdoor activities vary widely with the seasons, there is an array of year-round activities centered around the arts and entertainment.
Read along or contact us for the best things to do in Woodstock VT in the winter, spring/summer, and fall, as well as our recommended restaurants in Woodstock VT, and an overview of what a Woodstock VT shopping experience might look like!
Woodstock, VT Events Calendar
Wednesdays (09/01-18): Wagon Rides 11:00 am-3pm at Billings Farm Museum.
Wednesdays: Market on the Green, June 5-Oct 13, 3pm-6pm. Over 30 local vendors of cheese, veggies, bread, ice cream, pottery, arts, crafts. Live music!
Fridays: Foodway Fridays at Billings Farm and Museum. Discover how seasonal herbs and vegetables from the heirloom garden are used in historic recipes.
Fridays and Saturdays: Cooking classes at Odyssey Events. Pizza, Pasta, Souffles, and more — or ask for a custom class! Limited to 6 participants, BYOB and enjoy your creations!
7-8: Woodstock Art Festival: Over 30 Artists display and sell their art work on the village green during this 2 day event. Live music and food.
7-8: Fall Hunter Jumper Show at the Green Mountain Horse Association
13-14: Pentangle Arts Light Garden Festival, dusk-9:30pm
14: Woodstock History Center Old Time Fair, 1-4 pm
15: Woodstock Triple Crown Bike Race spanning The Aqueduct Trails, Mount Peg, and the trails at Suicide Six.
21-22: Forest Festival Weekend at The Marsh-Billings-Rockefeller National Historical Park. Horse-drawn wagon rides, woodworking and sawmill demonstrations, forester-led and self-guided hikes. 10am-5pm.
5-6: Autumn Wagon rides at Billings Farm
12-13: Apples and Crafts Fair and Food Truck Festival. Juried artwork, crafts, jewelry, and specialty food. 10am-5pm Saturday and 10am-4pm Sunday
12-13: Oktoberfast weekend at Suicide 6, closing the mountain biking season with a downhill fun race at Suice 6, enduro event on Mount peg, food and awards
12-13: Harvest Festival at Billings Farm & Museum
27: Halloween at Bilings Farm & Museum
28: Thanksgiving. We will be open! While many restaurants are closed on Thanksgiving Day, the Woodstock Inn and Resort hosts a traditional Thanksgiving Dinner open to the public – be sure to book early!
29-Dec 1: Thanksgiving Weekend at the Billings Farm & Museum. Discvoer how Thanksgiving was observed in 1890 at the farm.
13-15: 35th annual Wassail Weekend. This is Woodstock’s iconic celebration. Enter the holiday season with a whirlwind of winter wonderland complete with twinkling lights, horse-drawn carriage parade, historic home visits, concerts, caroling, yule log and more!
We are open for Christmas and New Year. Check back for restaurant specials and schedules for the holidays.
Maple Madness. When the days are warmer and the nights are still cold, the sap flows up through the sugar maple trees. During a few short weeks, the trees are tapped, and the sap is collected and boiled down to syrup. There is a unique opportunity to witness this process during maple madness by visiting participating sugar houses around Woodstock. Maple-related activities are organized on The Green and throughout Woodstock during this weekend. 2020 dates still TBD.
Things to do in the Spring and the Summer
There is just so much to do in the spring and summer in Woodstock, Vermont! There are fun events pretty much every weekend, either right here in Woodstock or in the towns nearby, and nature lends itself to so many enjoyable activities! And if all you want is to just sit in a comfy spot with your favorite beverage in one hand and favorite book in the other… then you’ve come to the right place too!
Here is our list of the top things to do in Woodstock, VT – call or email us for questions!
Billings Farm & Museum, the Marsh Billings Rockefeller National Historical Park, and the Rockefeller Mansion: a must-see in Woodstock.
The farm is both a working farm and a museum, with knowledgeable employees and volunteers extremely dedicated to their craft. Don’t miss the documentary (plays in a loop all day long), the farming museum in the barn (very interesting, you will learn a lot!), the farmhouse, and the live animals. Take a long stroll on the beautiful grounds where crops are growing and animals are grazing. Finally, pay a visit to the Jersey cows!
The Rockefeller Mansion guided tour is sure to please everyone, especially if you are a fan of history and architecture. Opens Memorial Day weekend.
Finally, the National Historical Park is perfect for a long or short hike – choose your level of difficulty.
The Farm and Museum, the Mansion, and the Park are among the top things to do in Woodstock, VT – don’t miss out!
After our hearty breakfast, hike up Mount Tom, then head down towards Billings Farm and Museum on easier carriage trails. On the way down, visit the Rockefeller Mansion, then head on to the farm and museum. After your visit, walk into town for a nice lunch and great shopping. For more details, read our blog post The Ideal 3-day Vermont Getaway, day 1.
President Coolidge Estate in Plymouth Notch
The birthplace and childhood village of the 30th President is off the beaten path, lovingly restored and preserved to tell the story of American democracy and the longstanding values of country life. A visit to Plymouth Notch will take you back to simpler times and stay in your memory.
After the guided tour, be sure to visit award-winning Plymouth Artisan Cheese (started by the President’s father as part of their general store), the General Store, and have a bite at the Wilder House.
The Vermont Institute of Natural Science (VINS)
VINS is “an environmental education, research, and avian rehabilitation organization” situated on 47 acres of nature preserve next to Quechee gorge. Check out their website for daily events such as reptile encounter, turtle time, raptor chats, live birds programs, or raptor feeding time. Plan to spend time hiking their grounds, listening in on programs, and learning a lot in a beautiful environment!
VINS is open every day, year-round, and is a mere 15-minute drive from the B&B, right before Quechee. Definitely also on top of the list of things to do in Woodstock, VT!
- Faulkner park right behind the B&B, leading to Marsh-Billings-Rockefeller National Historical Park and beautiful views of Woodstock from Mount Tom. Click here for a trail map.
- A portion of the Appalachian trail, crossing route 12 just 3 miles from Woodstock.
- Mount Peg, right on the other side of town.
- Around town and alongside the Ottauquechee river.
- Up the trails of Mount Peg and Mount Tom on a mountain bike, or take a short drive to Vermont’s newest lift-serviced trail park, Suicide Six Bike Park or to Killington’s mountain biking park.
- Bicycle rentals (and bike shops) available in town and at Suicide Six.
- Ask us where the swimming holes are in town (one is right across the street from the B&B!)
- Take a short, scenic drive up to Silver Lake.
Kayak and canoe
Wilderness Trails and the Vermont Flyfishing School offers several options, from a leisurely paddle on the Connecticut River to a more adventurous kayak trip on the White River, to canoe and kayaking in a wildlife sanctuary. Read more about this here!
Contact them for more info or ask us to set up your outing with them!
Wilderness Trails and the Vermont Flyfishing School will pick you up at the B&B bright and early to catch some Vermont trout and spend an unforgettable day in pristine nature. Ask us to book your fly fishing excursion or contact Pete directly. Definitely put this on your list of things to do in Woodstock, VT if you love nature and the outdoors!
Market on the Green every Wednesday from 3pm to 6pm: a curated selection of local farms, local artists, and local artisans offer the best of Vermont for you to enjoy right away or bring back home.
Feast & Field every Thursday evening in Barnard. Enjoy produce from local farms, amazing food and locally made beverages, a bonfire, and live music. A true farmers’ market in the middle of amazing nature. It does not get any better!
Covered bridges half marathon and pasta dinner in June
Vermont Symphony Orchestra summer tour in early July
Bookstock the last weekend in July
Taste of Woodstock in August
Quechee Balloon Festival during Fathers’ Day Weekend
Naked Table Project
For a full list and dates please check the Events tab above
Things to Do in the Fall
Weather permitting, all the activities mentioned in the spring and summer section are still available. However, fall is also a most magical season in Vermont, when the foliage becomes an attraction in itself.
If you are visiting between mid-September and late October, consider adding the following activities to your to-do:
- A guided bike tour (Check out Discovery Bike Tours)
- A photography class
- An outdoor painting class
- Or simply, follow our suggested foliage route and let your inspiration guide you!
Fall main event: Apple and Crafts Fair in October.
The Market on the Green and Feast & Field continue throughout mid-October.
For a full list and dates, please check the Events tab above.
Things to Do in the Winter
Woodstock is the birthplace of the ski lift in North America, so there is no shortage of things to do in Woodstock, VT in the winter.
- Alpine skiing at:
- Suicide Six (a 10-minute drive from the B&B), a smaller and sweet resort with a nice mix of beginner, intermediate, and advanced trails, a super cozy lodge complete with massive fireplace, bar, food, rentals, and shop.
- Killington, aka The Beast of the East. Killington is the Northeast’s largest ski resort and is open from late Fall to the Spring. Its Skyeship gondola is only 20 minutes from The Woodstocker B&B, while the base lodge is a 30-minute drive.
- Cross country skiing at the Nordic Center, 1 mile from the B&B, with beautifully groomed trails.
- Snowshoeing at the Nordic Center, 1 mile from the B&B. Enjoy their groomed trails or take your gear to Mount Tom, right behind the B&B!
- Fat biking at the Nordic Center or Killington.
Wassail Weekend. The 2nd Saturday in December, Woodstock celebrates the beginning of the holiday season with a horse-drawn carriage parade, caroling, wassailing (aka warming up with hot mulled cider), concerts, and more. Visit historic homes on the Green and Elm Streets, and get your shopping done in a picture-perfect New England town all decked out for the holidays. Nothing comes close to Christmas in Vermont!
Vermont Flurry: 3 days of ice carving on the green during President’s Day weekend.
Maple Madness: When the days get warmer but the nights are still cold, sap flows through the sugar maple trees. There is a short window to collect it: it’s called sugaring season. The sap is boiled down to a syrup consistency in the maple houses. There is nothing added to make maple syrup. Join us to celebrate the sweetest celebration in Vermont! Check out our Events page to find out which sugar houses will open their doors to the public.
For a full list and dates, please check the Events tab above.
Woodstock VT restaurants
Walking Distance from The Woodstocker B&B
The Prince & the Pauper
24 Elm Street
A landmark restaurant – Open daily
Long regarded as one of Vermont’s finest restaurants, The Prince & The Pauper now celebrates its 43rd year of excellence with executive chef Charles ‘Gavin’ Dziedziech. Their Prix Fixe Dinner Menu changes nightly and is inspired by flavors from around the globe. The Bistro Menu offers an eclectic selection of lighter fare.
61 Central Street
Creative cuisine – Open Wednesday through Saturday
By relying on their extensive network of small producers in the Upper Valley and cultivating relationships, they offer an ever-changing, seasonal variety of creative dishes executed to perfection. Wonderful cocktails as well.
Woodstock Inn and Resort
14 The Green
The Red Rooster
Semi- formal – Open daily
Their AAA Four Diamond Award winning restaurant, The Red Rooster, captures the essence of Vermont in its delightful satisfying dishes and semi-formal setting.
Richardson’s Tavern (no reservations)
Relaxed, tavern style – Open daily
The essence of Vermont and flavor-driven cuisine is paired with a bar featuring local craft brews and spirits at Richardson’s Tavern.
71 Central Street
Latin cuisine – Open Wednesday through Sunday
Note: Open 7 days through Foliage and 6 days during Summer
Where classic New England cuisine meets with subtle flavors of the Tropics.
The Daily Catch
61 Central Street
Pasta and seafood – Closed Tuesdays
A casual setting to enjoy pasta dishes and classic New England seafood.
And For Lunch…
Mon Vert Café – 28 Central Street, Woodstock
Soulfully Good Café – 67 Central Street, Woodstock
Driving Distance from The Woodstocker B&B
442 Woodstock Road, Woodstock (5-minute drive)
Casual and relaxed – Open daily (no reservations)
American cuisine with a twist. Generous, creative cuisine in a casual setting (order and pick-up at counter). Large list of local draft beers. Where the locals go.
The Lincoln Inn and Restaurant at The Covered Bridge (6-minute drive)
2709 W. Woodstock Rd. Woodstock
Critically acclaimed by Forbes, the Boston Globe, Zagat and more. Advanced reservations required.
A culinary destination with 4-course, 7-course or 12-course menus changing daily, using fresh, local ingredients.
1101 Cloudland Farm Rd, North Pomfret (15-minute drive)
BYOB – Thursday through Saturday
Weekly menus (check website). Farm to table using fresh, local ingredients from Cloudland and other local farms.
1780 Quechee Main Street, Quechee (15-minute drive)
Semi-formal – Open daily
Using fresh local ingredients, thoughtfully prepared creative American cuisine is served with the backdrop of the Ottauquechee River waterfall and covered bridge.
The Parker House
1792 Quechee Main Street, Quechee (15-minute drive)
Casual Elegance – Open Tuesday through Sunday
Modern, light-hearted approach to the quintessential Vermont dining experience and signature cocktails.
Barnard Inn – Max’s Tavern
5518 Route 12, Barnard (15-minute drive)
Casual – Open Tuesday through Saturday
From American cuisine to tavern style food. A 15-minute drive through a perfectly scenic Vermont landscape.
Ransom Tavern at Kedron Valley Inn
4778 South Road, South Woodstock (12-minute drive)
Relaxed – Open Wednesday through Sunday
Brick oven pizza and delicious cocktails.
506 On The River
1653 West Woodstock Road, Woodstock (3-minute drive)
Contemporary Vermont – Open daily
Continental cuisine and craft cocktails.
Woodstock VT shopping
WALKING DISTANCE FROM THE WOODSTOCKER B&B
Gillingham’s. Founded in 1886, this is a must-visit for anyone staying in Woodstock. A genuine Vermont general store, where you will find anything you need (including a nice wine selection).
Gallery on The Green
Fox Gallery Fine Arts
The Art Collaborative
The Vermont Flannel Co.
Encore (high-end consignment)
Who is Sylvia (vintage)
Home Décor, Gifts and Specialty
Clover Gift Shop: home décor, gifts, and now a line of CBD products (+ workshops and presentations)
Red Wagon (toy shop)
The Art Collaborative, Danforth Pewter, Unicorn, and the clothing boutiques also carry jewelry.
Beer, Wine and Alcohol
Enjoy our BYOB policy! The Woodstocker B&B provides glasses, ice buckets and an ice machine, as well as bottle openers for the enjoyment of your personnally purchased alcoholic beverages anywhere on the property.
Hops and Barley (at the East entrance of town) has a wonderful selection of local craft beers. If you don’t shop there for yourself while in Woodstock, consider stopping on your way home to bring back some hard to find beers.
Vermont Liquor store, also on route 4 East
Gillingham’s on Elm Street.
The Village Butcher on Elm Street.
LANDMARK STORES WITHIN DRIVING DISTANCE OF THE WOODSTOCKER B&B
This is just a selection of stores a discerning shopper might want to visit while in Woodstock.
In or Towards Bridgewater (route 4 West)
In or Towards Quechee (route 4 East)
Andrew Pearce bowls
Simon Pearce glass
Cabot Cheese and tasting station
Vermont Antique Mall
Deirdre Donnelly jewelry
Fat Hat Clothing Co.
In Windsor’s Artisan Park (route 5 south)
Vermont Famstead Cheese
In Weston, on Scenic Route 100 (south)
The Vermont Country Store