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Woodstock, Vermont Fall Bucket List


Fall is Woodstock’s busiest season, and we love the energy, warmth, and enthusiasm of locals and visitors alike.There’s good reason Many people flock to Woodstock every fall. Our typical small town is filled with the red, orange, yellow and gold colors of fall. Store windows are decorated with fall decorations, the mountains are covered in gorgeous foliage, and there are lots of fun holiday events happening. Whether you visit in September or October, you won’t be disappointed with the beauty of this charming town and there’s plenty to see and do.

Whether you’re a local or visiting Woodstock this fall, there’s plenty to do during the festival. We’re sharing all of our favorite fall pastimes and traditions from Woodstock that will keep you coming back for more every year.Don’t miss our g roundupGourmet Restaurants in Woodstock.

Woodstock, Vermont Fall Bucket List

TEDx Hartland Hill

On Saturday, September 23, TEDx Hartland Hill returns to Billings Farm and Museum with “The Art of Living.” A lineup of speakers will share their wisdom and experiences in finding purpose, meaning, and changing the world. This will be an incredible all-day event that you don’t want to miss!Grab tickets at the following locations TEDx Hartland Mountain Website!

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Apple & Crafts & Food Truck Festival

Another favorite annual event at Woodstock is Apple & Crafts & Food Truck Festival. The event is held on Maxham Meadow Way, just minutes from the village. This year’s Apple and Craft Fair will be held on Saturday, October 7 from 10am to 4pm and Sunday, October 8 from 10am to 3pm. Experience over 100 local artisans, craftsmen, specialty food producers and food trucks. This is a great place to buy gifts, souvenirs, and delicious sweet and savory items made in Vermont.

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Enjoy festive cocktails at Au Comptoir

There’s no better place to enjoy a seasonal cocktail in comfort than one of our favorite spots in town, Au Comptoir. Using fresh juices and locally sourced seasonal ingredients, Au Comptoir offers delicious drinks such as cardigana bourbon cocktail with notes of ginger and toasted pecans.

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Harvest Celebration at Billings Farm and Museum

Another wonderful seasonal event at Billings Farm and Museum is the annual harvest celebration. You won’t want to miss the two-day event on October 7th and 8th from 10am to 4pm. With everything from barn dances, pumpkin bowling, crafts, games, and live music to seasonal treats like cider donuts, spiced cider, homemade apple and pumpkin ice cream—you can’t go wrong! While you’re there, be sure to check out the current exhibitions, Photography exhibition of Vermont women farmers Author: Juan Carlos Gonzalez.

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Yankee Bookstore Click. read. like.  10.7.22

Little Shop of Horrors at the Grange Theater

Experience our own little town, the Grange Theatre, 19-29 October little shop of horrors. The sci-fi blockbuster musical is a hit during the holiday season. Go out for a date night or family night and enjoy this lively popular show in a beautiful, intimate theater setting.

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Apple and pumpkin picking

You can’t experience fall in New England without a classic apple or pumpkin picking trip. Head to one of our favorite spots to pick up some apples for apple crisp, cider, and more, then pick out a pumpkin to decorate or carve. This is a fun activity for the whole family to enjoy, regardless of age! Try one of our favorite local apple orchards: Moore’s Orchard, Whitman Brook Orchards and wellwood orchards. Try one of our favorite local pumpkin patches: Riverview Farm Plainfield, New Hampshire (about 30 minutes from Woodstock) or wellwood orchards in Springfield.

Pumpkin Apple Ice Cream

Would it really be autumn without pumpkin and apple ice cream? We happen to have some of the freshest, most delicious homemade ice cream in Woodstock.Check Woodstock Scoop, Billings Farm and Museum or mountain dairy Delicious Vermont-made ice cream with all the tastiest fall flavors.

Mon Vert Pumpkin Spice Latte

Calling all pumpkin spice latte fans, you’re sure to get your fill Monvet Cafe! Their delicious seasonal menu always has some super delicious fall specials. Their coffee is top-notch, not to mention their baked goods, breakfast, and lunch. Grab a latte and go for a walk in the village or sit on their outdoor patio.

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Autumn porg in Billings National Park
Pogue in Billings National Park

Picnic by the river

One of Woodstock’s best-kept secrets is this beautiful, private riverside spot located behind the Elm Street Historic Center.Get delicious sandwiches from Country Butcher Shop Then return to the historic center to enjoy the beautiful river views, gardens and picnic tables. It’s the perfect spot for a charming fall picnic in the village of Woodstock.

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Hiking Mount Tom and Mount Peg

The most spectacular way to see some of Woodstock’s most beautiful foliage is to hike Mount Tom or Mount Peg. You can access Mount Tom from Marsh-Billings-Rockefeller National Historical Park or Faulkner Park. The hike is light to moderate, about 4-6 miles round trip, and has a wide carriage trail that makes it easily accessible to joggers. The Faulkner Park Trail is a more rugged and narrow switchback trail, but there is a more direct route to the summit. At the top of the mountain you will find the most beautiful views of our little village, unrivaled during the fall foliage period.

Guests can access Mt. Peg from Golf Ave. and only a few minutes’ walk to the village of Woodstock. This trail is more family friendly and only takes an hour or less round trip. The top leads to a beautiful meadow overlooking the village of Woodstock and other mountains in the distance. This is another favorite, especially in the fall!

Things to do in Woodstock, Vermont this summer
green market

Stroll around town

You don’t need to do much to enjoy your time at Woodstock. The beautiful scenery speaks for itself. Take a stroll through the village, admire the fall decorations, and feel the holiday spirit in the air. Walk across the Covered Bridge and stroll along River Street and Mountain Avenue to Faulkner Park. As you stroll, admire the beautiful houses, decorated to look their best for the season. The path loops back to River Street and will take you back to the village.

green market

The Greenland Market runs every Wednesday from 3pm to 6pm until October 13th at the Woodstock Village Green. You can enjoy everything from produce to pizza, empanadas, ice cream, and shaved ice from over 30 local vendors! Not to mention, local artisans sell beautiful pottery, jewelry, and more. Enjoy live music and support local businesses at this beautiful community gathering.

Woodstock is one of the best places to visit in the fall! There is much to visit in this charming and quaint village, and the beautiful autumn foliage makes it an extra special time of year.

Are you planning a trip to Vermont or even Woodstock in the fall? let us know!

Disclosure: If you purchase something through links on this blog, we may earn an affiliate commission. We only recommend products that we personally recommend. thank you for your support.



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