We may be a little biased, but Vermont is one of the best places to experience fall, and an escape to Woodstock should be on everyone’s must-do list this autumn. Our little slice of Vermont is a great destination at any time of year, but our local businesses, farms and historic sites make fall exceptional with an exciting program of events throughout the season.

Read on for our selection of the best fall events in and around Woodstock, and be sure to get in touch for all your accommodation needs – 506 On the River Inn makes a great base for exploring the area!



September 23 to 24

Vermont Woodworking & Forest Festival 

This annual festival brings more than 20 master woodworkers together at Woodstock’s Billings Farm & Museum, where you’ll have a chance to browse their creations and watch live demonstrations. The Festival also highlights the neighboring Marsh-Billings-Rockefeller National Historical Park with walks, tours and wagon rides.


September 24

19th Century Apple & Cheese Harvest Festival & Apple Pie Baking Competition

Not only is this one of our favourite festivals of the season, it’s on the Vermont Chamber of Commerce’s Top Ten 2017 Fall Events list. A celebration of Johnny Appleseed’s birthday, this event at the Morrill Homestead celebrates all things apple, including cider that you can press yourself and an apple pie contest. You’ll also have the chance to sample the best of Vermont cheeses, explore Vermont’s first historic landmark, meet live farm animals, enjoy live music and much more.


September 30 to October 1

Billings Farm Pumpkin and Apple Celebration

Visit Billings Farm & Museum’s Pumpkin and Apple Celebration for a hands-on lesson with some of Vermont’s most important fall crops, as well as taste tests of the most delicious things made with them. This fun event includes practical demonstrations on pressing cider, making ice cream and cooking apple butter. You’ll also be able to play a round of pumpkin bowling and take a wagon ride around the farm.


October 7 and 8

Apples & Crafts Fair 2017

If you couldn’t tell, apple season is a big deal in Vermont! The Woodstock Recreation Center will host an Apples & Crafts Fair at Bailey’s Meadows, featuring delicious local delicacies and fun products from more than 100 juried craftspeople.


October 14 to 15

Autumn Wagon Ride Weekend

Horse-drawn wagon rides are the perfect way to take in the sights of Billings Farm & Museum, one of Woodstock’s most scenic attractions. You’ll get a tour of the farm, learning interesting tidbits as you go along, and of course see an incredible display of fall foliage. The weekend also includes fun and interactive activities, like your chance to get up close and personal with the farm’s Jersey cows and Southdown sheep.


October 29

A Family Halloween

If you’re in Woodstock for the weekend before Halloween, this family event at Billings Farm & Museum will let your little ones strut their stuff in their costumes and take part in host of fun activities. While the costume parades and their adorable participants will no doubt steal the show, pumpkins will get their fare share of attention at this farm-themed Halloween, with pumpkin carving, pumpkin ice cream cranking and fun pumpkin games. Other activities include (not too) scary stories and farm animal encounters. Children in costume attend for free, and each participant in the costume parades will receive a ribbon.



September 30

Killington Brewfest

Beer lovers delight – more than 100 craft beers from the region are brought together in one place with delicious food, fun activities and the stunning views of Vermont in late September.


October 7 to 9

Killington WitchCraft

Fun Halloween-themed activities for the whole family, including a haunted house and haunted maze, live music, craft beers and pumpkin painting, hoisting and catapulting.



Bike Tours

If you’re a cyclist, these bike tours are the perfect way to view Vermont’s natural beauty. With 506 On the River Inn serving as accommodation along the route, you’ll get out and explore the surrounding area and towns on these three- and four-day tours.

Sept. 29 to Oct. 1 and Oct. 6 to 8

Short and Very Sweet Vermont Bike Tour

Sept. 28 to Oct. 1

Rivers and Ridgelines Cycling Tour

Oct. 9 to 12

Beguiling Woodstock and Beyond Bike Tour


Market on the Green

Through Mid-October

Woodstock’s farmers market is a weekly tradition and a fun event throughout most of the year, but visit in autumn for delicious seasonal food and fall fun.


Dinner & Theatre

Through Oct. 22

Take in a show and support our community theatre with this fun package to see the Thursday and Saturday showings of the ArtisTree Music Theatre Festival. The evening begins with a three-course prix fixe meal at the 506 Bistro & Bar before performances at the Grange Theatre.


Apple Picking & Farm Visits

Vermont has a host of working farms that delight in showing visitors around, including Woodstock’s own Billings Farm & Museum and Sugarbush Farm. Visit these and other area farms for seasonal specialties and activities, including apple picking.


Foliage Tours

Three quarters of Vermont is covered with forests, and we boast the country’s highest density of maple trees, making our fall foliage one of the most incredible natural shows you can catch. However you like to experience the outdoors, whether biking, hiking or from the comfort of your car, be sure to tour Woodstock and the surrounding area for stunning sites and perfect photo opportunities.


To ensure availability throughout our busy fall season, be sure to book in advance. You can view our room selection here and book online and check availability here, or get in touch with us at 802-457-500 or reservations@ontheriverwoodstock.com.

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