1. VISIT LOCAL FARMS
Woodstock offers incredible farm experiences with Sugarbush Maple and Cheese Farm (free samples!) and Billings Farm & Museum, a fully functional farm and one of the finest outdoor history museums. Gather the whole family to say hello to friendly animals, get an inside look at how things are made, discover hidden gems on hundreds of acres, and even partake in a round of pumpkin bowling at the Harvest Celebration October 4-5, all under a vibrant canopy of leaves. Welcome to farm country.
Take a horse-drawn carriage ride through the picturesque forests within Marsh-Billings-Rockefeller National Historical Park. Beginning at Billings Farm & Museum, the journey follows the scenic carriage roads around the Pogue and ascends to the Overlook. Enjoy breathtaking vistas of the surrounding mountains and the charming town of Woodstock. The tour meanders through dense forests, past babbling brooks, along sweeping fields, all surrounded by natural beauty and rich history. Private wagonette rides are $500/ride and can accommodate up to six people.
2. GO APPLE AND PUMPKIN PICKING
Woodstock and the surrounding area have a plethora of choices for picking your own apples and pumpkins. Pick-your-own September through October at local orchards. Explore Moore’s Orchard in Pomfret or Whitman Brook Orchard in Quechee for a wide variety of deliciously fresh and ripe apples to choose from. For pumpkins– head to Fox Crossing/Ridgeline Farms in Pomfret or Riverview Farm in Plainfield, NH. Enjoy everything from ox cart rides to apple cider and baked goods for a well-rounded Vermont fall experience.
3. Head out on A HIKE
With the recent addition of the Ottauquechee River Trail, Woodstock is more walkable than ever—offering one of the best ways to experience fall foliage! There are so many great options for hikes in and around Woodstock, from a stroll through town to a hike up Mt Tom for a panoramic view of the quaint village below—and everything in between. Check out our recommendations for the area’s best hiking options, trail maps, and more.
Guided Hikes and Tours at Marsh-Billings-Rockefeller National Park
From architectural heritage tours to guided fall foliage hikes and watercolor workshops, there are a variety of opportunities for wonderful experiences at Vermont's only National Park, located right in Woodstock.
4. ENJOY LIVE MUSIC
One of the best things about summer and fall in Woodstock is the opportunity for outdoor music. Pull up a lawn chair, grab a blanket, and enjoy Vermont’s scenic landscape on Fable Farm and catch amazing live performances at Feast & Field in nearby Barnard. Enjoy outdoor music on Wednesday evenings at Artistree in Pomfret, every Wednesday at 6:30pm through September 24.
You can also catch live music at local spots including the Ottauquechee Yacht Club (Thursday, Saturday, and Monday evenings beginning at 6:30pm) and Market on the Green (Wednesdays through mid-October from 3-6pm). Pentangle Arts has several concerts lined up through the fall including Mystic Bowie's Talking Dreads.
5. FALCONRY EXPERIENCE WITH THE WOODSTOCK INN & RESORT
There’s nothing like watching a Harris's Hawk take flight, opening its 47” wingspan, its reddish-brown feathers blending with the vibrant foliage below. You can learn about the ancient pastime of falconry and even handle and fly a trained bird-of-prey at the Historic Rutherford Barn on Woodstock’s Hartland Hill Road. Bookings are made through the Woodstock Inn & Resort and are reservation only.
6. SHOP LOCAL IN THE WOODSTOCK VILLAGE
Admiring our historic storefronts and perusing the wares of boutique shops is a pastime all its own. Woodstock may be small but it has a diverse range of shops to meet all your Vermont souvenir, gifting, and personal needs. You can’t miss: Farmhouse Pottery, Woody’s Mercantile, Echo Market, and F.H. Gillingham and Sons. For more recommendations see our Woodstock Shopping Guide and Antique and Thrift Shopping in Woodstock.
6. TAKE A MOUNTAIN BIKE RIDE
Enjoy a mountain bike ride on any of the awesome trails in the Woodstock area. Woodstock is lucky to have a dedicated Mountain Biking community–WAMBA, maintaining our trails which are all free and accessible to the public. The network and variety of trails challenge and accommodate every level biker. Check out our trails here.
7. Experience the VINS CANOPY WALK
The Vermont Institute of Natural Science (VINS) in nearby Quechee is a nature lover’s wonderland, and the Canopy Walk, added in 2019, takes the nature center to new heights. Visit the rehabilitated birds in their outdoor enclosures and learn what it takes to care for these fascinating fowl. Then take to the treetops via an ADA-accessible boardwalk that rises as high as 81 feet (or four giraffes) above the forest floor, affording panoramic views of autumn’s colorful display, Dewey’s Mill Pond, and beyond.
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8. enjoy FARM-TO-TABLE DINING
For an unforgettable farm-to-table experience, make a reservation at Cloudland Farm, and enjoy the incredible drive during foliage on your way to a meal made with local ingredients. For a meal right in the village, head to Sante for small bites and entrees made with locally sourced ingredients and hand-crafted cocktails.
Inside the spectacular Red Barn at Kelly Way Gardens, enjoy a 4-course meal utilizing fresh, seasonal, and local ingredients anchored by produce from Kelly Way Gardens. But don't delay, because this reservation-only dinner series concludes in September.
9. get creative at artistree
Artistree is the Upper Valley’s haven for all things art and creativity. With everything from movement classes to painting, writing, cooking, performing, and more there are endless ways to get creative at Artistree. Explore the classes and workshops offered this fall and choose one that suits you!
10. explore woodstock area COVERED BRIDGES
Vermont has the most beautiful covered bridges and Woodstock is no different! Explore the covered bridges in Woodstock and the surrounding area to get a glimpse of New England's history and charm. Start with the Middle Covered Bridge in the village center adjacent to the town Green. Then head out of town to explore the Quechee Covered Bridge, Taftsville Covered Bridge, and Lincoln Covered Bridge.
FALL EVENTS IN WOODSTOCK VT
Market on the Green
Fall rounds out market season in Woodstock and Market on the Green is a local favorite! Enjoy farm fresh produce, tasty local treats, and local artisan goods for sale. You’ll find live music, a friendly environment, and gorgeous fall weather. Market on the Green is every Wednesday through October 15 from 3-6pm.
Woodstock Art Festival
The Woodstock Art Festival is a weekend-long event of fine art, music, spirits and food. Over 30 New England artists offer landscapes, portraits, photography and more. An opportunity to explore talented creatives and artists from throughout the region, don't miss this annual Woodstock event, September 6-7.
Harvest Celebration at Billings Farm & Museum
Fall at Billings Farm is truly magical! The gorgeous landscape, friendly farm animals, and festive events make it a fun and memorable place to be. Gather and celebrate the change of the season with harvest activities, food, and fun for the whole family October 4-5 from 10am-5pm at The Harvest Celebration. This lively two-day Harvest Celebration will feature traditional barn dancing, live music, pumpkin bowling, crafts, stories, and harvest activities.
50th Annual Apples & Crafts Fair and Food Truck Festival
The Apples & Crafts Fair is one of Woodstock's most popular annual events. Peruse over 100 vendors and purveyors of Vermont crafts, speciality food, art, and more. Don't miss this fall tradition, October 11-12.
Halloween in Woodstock
Woodstock is everything you dream of and more when you think of small-town New England Halloween. Maple and High Street close to traffic and homes transform with fog machines, orange and purple lights, and festive decor. Halloween in Woodstock is a sight to behold and brings out the childhood joy and wonder in all of us.
