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Woodstock Vermont

From The Blog Spice Things Up With These 11 Autumnal Events

Apples, hayrides, foliage, and pumpkin spice lattes, oh my! As the air turns crisp, trees are bursting with yellow, orange, and fiery red hues – marking the start of one of the most gorgeous seasons in Woodstock. Our village will put a spell on you with this bewitching scenery and these 11 can’t-miss events of the season:

A Family Halloween

October 28, 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.

A Family Halloween
Thanksgiving Weekend at the Billings Farm

Thanksgiving Weekend at the Billings Farm

November 23 – 25, 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!

Photo by Emmy Walden Fox


6th Annual Pentangle Arts Light Garden

September 21 – 22, 6:30 – 10:30 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. Walk on 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 complete with cupcakes, drinks, and music by Midlife Crisis.

Forest Festival Weekend

September 22, 10 AM – 4 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: woodworking crafts, animal Olympics, puppet shows, scavenger hunts
  • Forester-led and self-guided hikes

5th Annual Old Time Fair

September 22, 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!

Old Time Fair at the Woodstock History Center
Old Time Fair at the Woodstock History Center
Apples on a string at Pumpkin and Apple Celebration
Billings Farm staff photo
Visitors trying the apples-on-a-string activity.

Pumpkin and Apple Celebration

September 29 – 30, 10 AM – 5 PM

Just a hop, skip, and a jump from Woodstock village, you’ll find the fully-operating Billings Farm & Museum abuzz with their Pumpkin and Apple Celebration! Here you’ll find a cornucopia of hands-on programs centered around these two essential fall crops, including:

  • Apple tasting
  • Cider pressing
  • Apples-on-a-string
  • Apple and pumpkin ice cream making
  • Pumpkin bowling
  • Cooking with apple butter in the farmhouse
  • Wagon rides
Starline Rhythm Boys

ArtisTree and Suicide Six Ski Area present a Swingdance!

October 5, 7:30 – 9:30 PM

Vermont’s premier honky-tonk and rockabilly trio is coming to Suicide Six to get you in the swing of things! Join the Starline Rhythm Boys as they bring down the Base Lodge with soulful sounds, compliments of 100+ years combined experience in various bands (including Danny Coane with The Throbulators, Al Lemery with Badge and Billy Bratcher’s big-time stint with Wayne "The Train" Hancock). Lessons available at 7 PM, dancing starts at 7:30 PM. Individual tickets are $20, $35 for couples.

4th Annual en Plein Air Painting Festival

September 29 – October 5

At this unique festival, capture your singular perspective of the gloriously diverse shades of nature on canvas. Paint in the open air of the Ottauquechee River watershed ecosystem during this festival centered around mindful, artistic exploration and inspiration – then submit your work for an artist competition! Participation is $40 for adults, free for youths 17 and under.

Woodstock Recreation Center’s 46th Annual Apples & Crafts Fair

Saturday, October 6th 10 AM – 5 PM, Sunday, October 7th 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 at Bailey’s Meadow for:

  • Juried artwork
  • Crafts
  • Jewelry
  • Specialty foods including soup, chilli, ice cream, apple crisp

Admission is $4 per person, children 12 & Under are free.

    Harvest Weekend at the Billings Farm & Museum

    October 6 – 7 PM, 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!

    Harvest Weekend

    Peak to Peak to Pogue

    October 13, 10 AM – 2:30 PM

    Get an up-close-and-personal look at Woodstock’s vibrant trail foliage, then get a panoramic perspective from the top with Peak to Peak to Pogue! Amble from scenic viewpoint to scenic viewpoint, summiting Mount Peg and Mount Tom and enjoying snacks, activities, and insights from guides along the way. This event is free and offers a great opportunity for the whole family to get in some leaf peeping!