The Green Mountain Horse Association's Fall Hunter Jumper Show
September 7-8
In the pristine country landscape of South Woodstock, you can drive right up and tailgate for a beautiful fall afternoon of foliage and derby rounds! Horse lovers and their families, this is your chance to grab the reins and compete in one of the most exciting disciplines of horseback riding, or sit back and enjoy the show.
The Woodstock Art Festival
September 7-8
Amble through the Woodstock village green and admire spectacular pieces by local artists at this festival of creative creations! This event features live music, food, and of course, art by over 30 vendors available for sale.
Canceled - Pentangle Arts' Light Garden Festival
September 13 – 14, dusk – 9:30 PM
Walk through an enchanting wonderland of illuminated art during this unparalleled exhibit. Bursting from a series of “garden plots,” these luminous sculptures are designed by local artists and feature whimsical and creative uses of light via recycled materials. Traverse the village path lit by these works of art, vote for your favorite, then celebrate the winners at the Awards Ceremony on Saturday at 8 PM.
The Woodstock History Center's Old Time Fair
September 14, 1 – 4 PM
Take a step back in time and celebrate fall the old-fashioned way! For just 25 cents, you can join the Woodstock History Center for historical food, games, crafts, live music, a photo booth with vintage clothes, and more. Happening rain or shine!
The Woodstock Triple Crown at Suicide Six Bike Park
September 15, 10 AM – 2 PM
Traverse three heart-pumping mountain bike networks in an enduro-style race you won't forget!
Spanning the Aqueduct Trails, Mt Peg, all the way to the bike park at Suicide Six, this race is going to be epic.
Forest Festival Weekend
September 21-22, 10 AM – 5 PM
Explore Marsh-Billings-Rockefeller National Historical Park in all its autumnal glory with this action-packed event that’s free for all. Choose from activities that’ll have the whole family falling for Woodstock, including:
- Horse-drawn wagon rides
- Woodworking and sawmill demonstrations
- Family activities including making a walking stick, decorating wood medallions, and playing with wooden games
- Forester-led and self-guided hikes
Autumn Wagon Ride Weekend
October 5-6, 10 AM – 5 PM
Just a hop, skip, and a jump from Woodstock village, you’ll find the fully-operational Billings Farm & Museum bustling with narrated wagon rides during peak fall foliage!
Here you’ll also find a cornucopia of hands-on programs for the whole family.
Woodstock Recreation Center’s Apples & Crafts Fair & Food Truck Festival
Saturday, October 12th 10 AM – 5 PM, Sunday, October 13th 10 AM – 4 PM
Columbus Day weekend, gather with attendees and 100+ juried craftspeople and specialty food producers at this family fun fair! Peruse tent after tent in the open autumn air for:
- Juried artwork
- Crafts
- Jewelry
- Specialty foods including soup, chili, ice cream, apple crisp
Admission is $4 per person, children 12 & under are free.
Oktoberfast Weekend
October 12-13
Close out an awesome season of mountain biking with a downhill fun race at Suicide Six, endure event on the Mt Peg trails, tasty food, and of course, awards! Because what better way is there to enjoy the fall foliage than by whipping through the vibrant autumn trees?
Harvest Festival at the Billings Farm & Museum
October 12-13, 10 AM – 5 PM
Billings is back on our list with more seasonal celebrations! Visit the farm for a traditional Vermont harvest jubilee with a husking bee, barn dance, cider pressing, root vegetable harvesting, "putting food by," and more. After your work on the farm is done, warm up with a serving of hot spiced cider and doughnuts!
A Family Halloween
October 27, 10 AM – 5 PM
Eat, drink, and be scary! There’s Halloween fun for all ages at Billings Farm & Museum, including doughnuts-on-a-string, pumpkin carving, spooky stories, wagon rides, and lots more. Then, jump into the spotlight and join the costume parades at 12:00 and 2:00 PM to showcase your All Hollows’ Eve duds. Children in costume are admitted free when accompanied by an adult.
Thanksgiving Weekend at the Billings Farm
November 29 - December 1, 10 AM – 4 PM
Step back into 1890 and discover how Thanksgiving was observed in the Billings Farmhouse—from preparations, to the menu and entertainment.
Then step outside into the cool November air for an invigorating wagon ride!
