We didn’t plan on falling in love with Woodstock, Vermont it just happened somewhere between our kids’ excited squeals in the backseat and that first glimpse of the rolling green hills that wrap around the village like a warm hug.
What we found wasn’t just a pretty New England town.
It was white picket fences that reminded us of old storybooks, covered bridges our kids begged to run across “one more time,” and quiet riverside trails where we walked slowly as a family, noticing how the entire landscape shifts its personality with each season the fiery glow of fall, the stillness of winter, the bloom of spring, and the soft gold of summer.
Woodstock has a way of making you slow down without even realizing it. Coffee runs turn into morning strolls. Simple errands turn into moments you tuck away forever.
And every maple leaf, every snowflake, every sunrise feels strangely intentional like the town wants you to notice the little things again.
Here’s your complete guide to 30 wonderful things to do in Woodstock, Vermont in every season.
A Quick Glimpse of Woodstock, Vermont
Founded in 1761, Woodstock is the kind of small town that feels frozen in time but in the best way.
Its streets are lined with Federal-style homes, charming boutiques, and tree-lined greens.
The Ottauquechee River winds through town, adding gentle rhythm to the village’s life.
Woodstock has been named one of “America’s Prettiest Small Towns” by Condé Nast Traveler, and it’s easy to see why.
With its covered bridges, farm-to-table dining, outdoor adventures, and historical depth, the village perfectly embodies New England’s spirit.
Spring in Woodstock, VT: Blooms, Maple, and Rebirth
As Vermont’s snow melts and the maple sap starts to flow, Woodstock awakens in color and scent. It’s a season of rebirth perfect for exploring farms, gardens, and fresh-air adventures.
1. Visit Sugarbush Farm and Learn the Art of Maple Making
Sugarbush Farm became one of our family’s favorite stops in Vermont almost instantly.
As soon as we pulled up the quiet hill and saw the view of the Green Mountains, it felt like the kind of place where you could slow down and just enjoy being together.
The farm is warm and welcoming, and our kids loved exploring the sugarhouse and seeing how maple syrup is made.
Walking through the tapping process, smelling the warm steam, and tasting syrup right from the source made the visit feel special for all of us.
Larry and Betsy Luce have been running the farm for decades, and you can feel that family touch everywhere you go. Nothing feels rushed or touristy just simple, genuine hospitality.
Before we left, we picked up their wax-wrapped cheddar, smoked cheese, and local jams though most of it didn’t survive the car ride home.
2. Wander Through the Marsh-Billings-Rockefeller National Historical Park
Our family loved visiting Vermont’s only national park, especially in spring when everything feels fresh and new.
The trails wind through maple and hemlock forests, and the soft green hillsides look like they’re just waking up for the season.
The park also shares the history of conservation leaders like George Perkins Marsh, Frederick Billings, and the Rockefeller family something we found surprisingly interesting as we explored.
We enjoyed a guided tour of the Rockefeller Mansion, walked through the gardens, and took a relaxed stroll along the quiet carriage roads.
Why Visit in Spring: The gardens start blooming beautifully, the air feels crisp and new, and the trails stay calm and peaceful before the summer visitors roll in.
3. Stroll the Woodstock Village Green
In spring, the Village Green became one of our family’s favorite spots.
Tulips, dogwoods, and lilacs brightened the lawns, and we loved seeing neighbors and kids strolling around after the long winter.
Surrounded by colonial-era homes and the Woodstock Inn, it felt like stepping into an old Vermont storybook peaceful, cozy, and full of charm.
We grabbed coffee from Mon Vert Café, found a bench to sit together, and watched life unfold around us. Simple, relaxing, and the perfect little family moment.
4. Explore the Dana House Museum
Built in the early 1800s, the Dana House provides a glimpse into early Vermont life.
Inside, you’ll find handcrafted furniture, household artifacts, and antique clothing that tell the story of Woodstock’s early settlers.
It’s a small but beautifully preserved museum that helps you appreciate the village’s history before it became a beloved tourist destination.
5. Take a Scenic Drive on Route 100
Spring is the ideal time for a slow drive down Route 100, often called Vermont’s prettiest highway.
Rolling past farms, sugarhouses, and mountain ridges, it’s pure countryside serenity. Bring your camera you’ll pass countless photo-worthy barns and riverside scenes.
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Summer in Woodstock, VT: Festivals, Hikes, and Farm-Fresh Delights
Summer in Woodstock is full of light and energy.
The days are long, the rivers sparkle, and the community feels alive with events, concerts, and farm markets.
6. Hike Mount Tom for a Breathtaking View
Rising behind the village, Mount Tom offers one of the best short hikes in Vermont.
The Faulkner Trail leads you through shaded woods before opening up to sweeping views of Woodstock village, the covered bridge, and distant peaks.
The climb takes about 45–60 minutes each way, making it perfect for a morning adventure before brunch in town.
Best Time: Early morning or sunset the lighting across the valley is stunning.
7. Kayak or Canoe on the Ottauquechee River
The Ottauquechee River meanders gently through Woodstock, offering calm waters for kayaking and canoeing.
Rentals are available locally, and you can paddle past wildflower-dotted banks and open meadows.
Insider Tip: After your paddle, grab lunch at Worthy Kitchen a casual spot known for Vermont craft beer and farm-sourced burgers.
8. Attend a Summer Concert on the Village Green
On warm evenings, the Woodstock Village Green transforms into a lively outdoor stage.
Local musicians, folk bands, and jazz trios perform as families spread out on blankets under the fading light.
Bring a picnic and join locals in one of Vermont’s sweetest small-town traditions.
9. Visit Billings Farm & Museum
Summer is the busiest and most beautiful time at Billings Farm. It’s an operational dairy farm and living museum that lets visitors experience Vermont’s agricultural heritage.
You can meet the cows, learn about butter churning, tour historic barns, and enjoy exhibits about 19th-century farm life. Kids love it and adults find it quietly fascinating.
10. Shop Local at the Woodstock Farmers Market
Open from May to October, the Woodstock Farmers Market is a celebration of everything Vermont grows and makes.
You’ll find artisan cheeses, maple granola, fresh bread, local produce, and handmade crafts.
It’s also a great place to grab lunch their deli serves sandwiches and salads that highlight regional flavors.
11. Drive to Quechee Gorge
A 10-minute drive east of town, Quechee Gorge is known as “Vermont’s Little Grand Canyon.”
The gorge plunges 165 feet deep, and the views from the bridge are unforgettable.
Follow the short trail to the riverbed for a picnic or a refreshing dip.
12. Visit Simon Pearce Glassworks in Queche
Just beyond the gorge lies Simon Pearce, one of Vermont’s most iconic artisan studios. You can watch glassblowers craft delicate bowls, lamps, and vases by hand a mesmerizing art form.
After your tour, dine at the on-site restaurant overlooking a waterfall-powered mill.
13. Visit Artistree Community Arts Center
Art thrives in Woodstock. Artistree hosts seasonal exhibits, workshops, and performances, all within a restored barn surrounded by meadows.
In summer, the outdoor sculpture garden becomes a peaceful place to wander.
14. Take a Scenic Bike Ride Through the Countryside
Cycling enthusiasts will love the quiet backroads around Woodstock.
Ride past farms, streams, and wildflower fields and stop at Long Trail Brewing Co. for a refreshing drink.
15. Stay at the Woodstock Inn & Resort
Summer is the perfect time to enjoy the Woodstock Inn’s lush gardens and outdoor terrace.
The resort also offers tennis, golf, and bike rentals plus a spa that’s one of Vermont’s best.
Fall in Woodstock, VT: The Season of Gold and Fire
If you could visit Woodstock only once, fall might be the time to do it.
From late September through October, the hills transform into fiery shades of orange, red, and yellow. Every road, trail, and bridge looks cinematic.
16. Drive the Route 12 Loop for Fall Foliage
From Woodstock, drive north along Route 12 toward Barnard.
The winding road takes you past mirror-like ponds and crimson hills.
Stop at Silver Lake State Park for photos it’s one of the best leaf-peeping spots in Vermont.
17. Attend the Annual Harvest Festival
Held in early October, this festival celebrates the season with local crafts, pumpkin displays, hayrides, and live folk music.
It’s hosted by Billings Farm and draws visitors from across the state.
18. Take a Foliage Hike Up Mount Peg
Quieter than Mount Tom, Mount Peg offers equally beautiful views especially in fall.
The short hike rewards you with panoramic views of Woodstock’s blazing treetops and church steeples below.
19. Explore Local Covered Bridges
Woodstock is home to some of Vermont’s most charming covered bridges, including the Middle Covered Bridge, which spans the Ottauquechee River right in town.
Drive a little further to find Taftsville Covered Bridge — one of Vermont’s oldest — glowing crimson against the fall colors.
20. Go Apple Picking at Whitman Brook Orchard
Nothing says autumn like apple picking. Whitman Brook Orchard is just outside town, offering crisp apples, cider donuts, and sweeping valley views.
21. Visit Local Breweries and Cider Houses
Cooler air calls for cozy drinks. Visit Long Trail Brewing Co. for hearty beers or Fable Farm Cider in Barnard for small-batch hard cider tastings made from heritage apples.
Winter in Woodstock, VT: Snow, Lights, and Comfort
When the snow arrives, Woodstock transforms into a fairytale village. Covered bridges are dusted with white, and twinkling lights glow from shop windows. Winter here is quiet, comforting, and deeply nostalgic.
22. Attend the Woodstock Wassail Weekend
One of the most enchanting holiday events in New England, Wassail Weekend fills the streets with carolers, horse-drawn carriages, and lantern-lit parades. Historic homes open for tours, and the village green becomes a winter wonderland.
23. Ski or Snowboard at Suicide Six
Located just a short drive away, Suicide Six is one of America’s oldest ski resorts — small, family-friendly, and full of charm. It’s great for beginners, and the lodge offers fireside drinks afterward.
24. Go Snowshoeing in Marsh-Billings-Rockefeller Park
When the park’s trails are covered in snow, they become perfect for snowshoeing. The quiet of the forest, broken only by the sound of your steps, is peaceful beyond words.
25. Enjoy a Sleigh Ride Through the Woods
Take a horse-drawn sleigh ride through fields and forest paths at one of the local farms. Wrapped in warm blankets as snowflakes fall, you’ll feel like you’ve stepped into a Vermont painting.
26. Cozy Up by the Fire at the Woodstock Inn
After a day in the snow, few things feel better than sipping hot cocoa by the fire at the Woodstock Inn. The inn’s lounge is warm, intimate, and decorated with rustic New England flair.
27. Visit Local Art Galleries and Shops
Winter is ideal for indoor exploration. Visit galleries like Gallery on the Green or Woodstock Gallery, both featuring Vermont artists inspired by nature and the seasons.
28. Take a Day Trip to Killington
Just 30 minutes away, Killington Resort offers world-class skiing and snowboarding for more advanced adventurers. Return to Woodstock in the evening for a quiet dinner and cozy rest.
29. Dine at The Prince & The Pauper
A Woodstock classic. With candlelit tables and a menu featuring locally sourced dishes, The Prince & The Pauper delivers an unforgettable fine dining experience.
30. Stay in a Historic Bed and Breakfast
For the perfect winter escape, stay at a historic B&B like The Village Inn of Woodstock or The Woodstocker B&B. Think warm fireplaces, homemade breakfasts, and Vermont hospitality at its finest.
Final Thoughts: The Year-Round Magic of Woodstock, VT
Woodstock isn’t about rushing from one attraction to another. It’s about savoring the small things — a walk across the covered bridge, a steaming cup of cider, a friendly hello from a shop owner. Each season here tells its own story, and by the time you leave, you’ll already be dreaming of your return
