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 on October 12th and 13th—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 $850/ride and can accommodate up to six people. Rides are approximately 2 hours and 30 minutes long.
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.
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.
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 as well.
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 shopping recommendations see our Woodstock Shopping Guide.
Don't miss Woodstock's Second Saturdays Sip and Shop This Fall
The second Saturday of every month, September - December, enjoy special drinks and surprises at participating stores in the village from 5-7pm. Sip and Shop Dates: 9/14, 10/12, 11/9, & 12/14.
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.
Don't miss Woodstock's Fall Food Pop Up with a variety of cuisines in the heart of the village, Saturdays, Sundays, and Mondays during September and October. Check out the full schedule and all the vendors here.
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 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
The fall rounds out market season in Woodstock and the Wednesday 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 16 from 3-6pm.
Woodstock's Fall Food Pop-Up
During the months of September-October, enjoy a variety of delicious food with Woodstock's Fall Food Pop-Up. On Saturdays, Sundays, and Mondays through the end of October, dine on everything from BBQ to Baked Goods on the Village Green and at History Center Parking Lot. See the full line-up of dates, hours and vendors here.
Forest Festival
Forest Festival at Marsh-Billings-Rockefeller National Historical Park is September 21st from 10am-4pm. This event is free! Take a horse-drawn wagon ride, try your hand at woodworking, or explore the forest on a guided nature walk. Witness the whole forest product cycle in action, from horse-logging, to board cutting with a portable sawmill to woodcraft demonstrations. Visit activity hubs to meet members of the Abenaki community, local artisans, and outreach partners.
Trek to the Top
Join Trek to the Top on Saturday, October 5th for a free event at the Marsh-Billings-Rockefeller National Historical Park. Hike to the South Peak of Mount Tom to meet Park Rangers for crafts, treats, and more! Hike to South Peak from Faulkner Park, Prosper Rd, or the Billings Farm & Museum. For information on hiking trails, visit the Hiking Trails page or the Carriage Barn Visitor Center to pick up a map! Hiking trails to the South Peak range from 1-4 miles.
50th Annual Apples & Crafts Fair and Food Truck Festival
The Apples & Crafts Fair is a favorite annual event in Woodstock from October 12th-13th, 10 am-4 pm. Shop with over 100 vendors and purveyors of Vermont crafts, specialty food producers, and food trucks.
Fall at Billings Farm
Fall at Billings Farm is truly magical! The gorgeous landscape, friendly farm animals, and festive events make it such a fun place to be. Gather and celebrate the change of the season with harvest activities, food, and fun for the whole family on Saturday, October 12 & Sunday, October 13, 10 am-5 pm at The Harvest Celebration. This lively two-day Harvest Celebration will feature traditional barn dancing, live music, pumpkin bowling, crafts, stories, and harvest activities.
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 $850/ride and can accommodate up to six people. Rides are approximately 2 hours and 30 minutes long.
Get into the Halloween spirit with a “Life & Death Tour” of Billings Farm’s 1890 Farm Manager’s House and the mansion at the Marsh-Billings-Rockefeller National Historical Park, October 25-26. Costumed tour guides will share tales of the people who lived and died on the Billings farm and estate while exploring Victorian-era superstitions, views on death, and mourning traditions through artifacts and stories. Enjoy the slightly spooky and super sweet Family Halloween on Sunday, October 27, 10am–5pm. At this spooktacular Halloween on the farm, there will be fun for the whole family with hayrides, costume parades, and more!
Fall Dressage Show & Vermont Fall Getaway
The Fall Dressage Show & Vermont Fall Getaway is the perfect way for horse lovers to enjoy the fall season in picturesque South Woodstock, Vermont. Participate in the show or see the action as a spectator!
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 down and become flooded with families in festive wear. 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!
