Woodstock, VT Fall Bucket List

By Kelley Boymer
18 Sep 2023

Photography by Craig Mackay

Fall is our busiest season in Woodstock and we love the energy, warmth and enthusiasm of both locals and tourist alike. There’s good reason why so many people flock to Woodstock each fall. Our quintessential town comes to life with autumn shades of red, orange, yellow and gold. Store windows are decked out in fall decor, the mountains are blanketed in gorgeous foliage and there are so many fun, festive events happening. Whether you are visiting in September or October the beauty of this charming town will not disappoint and there is so much to see and do while in town.

Whether you are a local or visiting Woodstock this fall there is so much to do during this festive season. We’re sharing all of our favorite fall pastimes and traditions in Woodstock that will keep you coming back for more each year. Don’t miss our round up of great restaurants in Woodstock.

Woodstock, VT Fall Bucket List

TEDx Hartland Hill

On Saturday, September 23rd TEDx Hartland Hill is returning to Billings Farm & Museum with “The Art of Living”. A lineup of speakers will share their wisdom and experiences around finding purpose, meaning and making a difference in the world. This is going to be an incredible daylong event you won’t want to miss! Grab tickets at the TEDx Hartland Hill website!

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Apples & Crafts and Food Truck Festival

Another favorite annual event in Woodstock is the Apples & Crafts and Food Truck Festival. This event takes place just a few minutes outside of the village on Maxham Meadow Way. Catch the Apples & Crafts Fair this year on Saturday, October 7th from 10am-4pm and Sunday October 8th, from 10am-3pm. Experience over 100 local artisans, craftspeople, specialty food producers and food trucks. A great place to stock up on gifts, souvenirs and delicious Vermont made sweet and savory treats.

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Get a Festive Cocktail at Au Comptoir

There’s no better place to cozy up with a seasonal cocktail than one of our favorite spots in town, Au Comptoir. Using fresh juices and locally sourced seasonal ingredients Au Comptoir has delicious drinks like The Cardigan, a bourbon cocktail with notes of ginger and toasted pecans.

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Harvest Celebration at Billings Farm & Museum

Another wonderful seasonal event at Billings Farm & Museum is the annual Harvest Celebration. You won’t want to miss this two-day event on October 7th and 8th from 10am-4pm. With everything from barn dancing, pumpkin bowling, crafts, games, live music, seasonal foods like cider donuts, spiced cider, homemade apple and pumpkin ice cream– you can’t go wrong! Be sure to check out the current exhibit while you’re there, Vermont Female Farmers Photography Exhibition by JuanCarlos González.

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yankee book shop Click. Read. Love. 10.7.22

Little Shop of Horrors at the Grange Theater

From October 19th-29th experience our very own small town, Grange Theater in action with Little Shop of Horrors. This sci-fi smash musical is a great festive seasonal hit. Head out on a date night or family night out and enjoy this hilarious, popular show in a beautifully intimate theater setting.

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Apple & Pumpkin Picking

You can’t do fall in New England without a classic apple or pumpkin picking excursion. Head to one of our favorite spots and load up on apples to make apple crisp, cider and more and pick your pumpkins for decorating or carving. This is a fun activity for the whole family to enjoy, no matter the age! Try one of our favorite local apple orchards: Moore’s OrchardWhitman Brook Orchard and Wellwood Orchards. Try one of our favorite local pumpkin patches: Riverview Farm in Plainfield, NH (about 30 minutes from Woodstock) or Wellwood Orchards in Springfield.

Pumpkin and Apple Ice Cream

Is it truly fall without pumpkin and apple ice cream? And we just happen to have some of the freshest, most delicious homemade ice cream around, right in Woodstock. Check out Woodstock Scoops, Billings Farm & Museum or the Mountain Creamery for delicious Vermont made ice cream in all the yummiest fall flavors.

Pumpkin Spice Latte from Mon Vert

Calling all pumpkin spice latte fans, you can be sure to get your fill at Mon Vert Cafe! Their delicious seasonal menu always has some super yummy fall specials. Their coffees are top notch, not to mention their baked goods, breakfast and lunch. Grab a latte to go and take a stroll around the village or enjoy sitting on their outdoor patio.

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the pogue in fall at billings national park
the pogue at billings national park

Have a Picnic By the River

One of Woodstock’s best kept secrets is this beautiful, intimate river spot back behind the History Center on Elm Street. Grab a delicious sandwich from the Village Butcher Shop and head back behind the History Center for beautiful river views, gardens and picnic tables. It’s the perfect spot to enjoy a charming fall picnic in the Woodstock village.

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Hike Mt. Tom & Mt. Peg

The most spectacular way to see the best of Woodstock’s foliage is to hike Mt. Tom or Mt. Peg. You can access Mt. Tom from the Marsh-Billings-Rockefeller National Historic Park or Faulkner Park. The hike is mild to moderate and about 4-6 miles round trip with wide carriage trails that are easily accessible with joggers. The Faulkner Park trails are a bit more rugged and narrow switchback trails, but have a more direct route to the top. At the peak you will find the most picturesque view of our little village that cannot be beat during fall foliage.

Mt. Peg can be accessed from Golf Ave. just a few minutes walking distance from the village of Woodstock. This trail is a bit more family friendly and can be hiked in an hour or less roundtrip. The peak opens to a beautiful meadow overlooking the village of Woodstock and other mountains in the distance. This is another favorite, especially during the fall!

Things To Do In Woodstock VT This Summer
market on the green

Take a Stroll Around Town

You don’t have to do much to enjoy your time in Woodstock. The beautiful sights speak for themselves. Take a stroll around the village to see the fall decor and feel the festive vibes in the air. Take a walk over the Middle Covered Bridge and stroll down River Street and Mountain Ave. to Faulkner Park. Admire the beautiful homes decked out in their seasonal best as you meander. This loops back around to River Street which will bring you back into the village.

Market on the Green

Market on the Green continues every Wednesday through October 13th from 3-6pm on the Village Green in Woodstock. You can enjoy over 30 local vendors with everything from produce, to pizza, empanadas, ice cream and shave ice! Not to mention, local artisans with beautiful pieces of pottery, jewelry and more for sale. Enjoy live music and this beautiful gathering of community to support local businesses.

Woodstock is one of the best places to visit during the fall! This charming, quaint village has so much to offer and the beauty of the fall foliage makes it an extra special time of year.

Are you planning a fall trip to Vermont or even Woodstock? Let us know!

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  1. This just looks like heaven on earth. Those leaves!! And that cocktail is STUNNING!

    xo Jessica
    an indigo day

    9.19.23 | Reply

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