Is a fall weekend in Woodstock, Vermont, on your bucket list for this year? This idyllic town offers a lot of options for visitors hoping to catch a glimpse of the changing leaves.

The warm-toned foliage enveloping the trees in the United States’ northeastern region is what beckons swamps of tourists to the state of Vermont each fall. The cozy town of Woodstock sets the scene for autumnal celebrations in the final stretch of the tourist season, mirroring the likes of a Gilmore Girls episode with its homey embrace.

In search of maple syrup, apple cider donuts, and a peek at the copper-colored tree tops, my friend and I drove 4.5 hours from the congested center of New York City to the open-aired countryside of Vermont in early November. While our end-of-season trip offered little leaves left to admire, our weekend in Woodstock still resulted in a mood-lifting reunion topped with quirky entertainment and New England comfort food.

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Things to Do in on a Fall Weekend in Woodstock

Explore Downtown Woodstock

Downtown Woodstock is the ideal setting for book lovers, creatives, retirees, and community-focused souls. While the town’s main square can be explored in a short period of time, I encourage you to meander through the shops at a slower pace. Stick your nose in a book at The Yankee Bookshop or the refurbished Norman Williams Public Library, grab an apple cider donut from Mon Vert Cafe, and find a pile of leaves on the grand lawn of The Woodstock Inn and Resort. This characteristic town has a handful of shops, galleries, and restaurants to enjoy as the day goes by.

It will be impossible to miss Woodstock’s Middle Covered Bridge, one of the 100+ still standing in the state. This wooden overpass is placed in the heart of Woodstock and is a favorable photo spot for many, even attracting a pair of newlyweds on our day of touring. Walk on the attached pedestrian pathway to peer over the Ottauquechee River at least once during your fall weekend in Woodstock.

See a Show at Woolen Mill Comedy Club

Seeing a comedy act during our fall weekend in Woodstock was not in our original plans, but after happening to see a sign advertising a one-woman musical comedy, my friend and I were too intrigued to turn this down, especially as our night had wrapped up earlier than expected. After purchasing tickets and navigating our way to this unconventional BYOB venue, we were seated in an intimate room with other unsuspecting attendees, not quite sure what to expect. 

What followed was almost two hours of kooky humor and scattered laughter. We were glad we followed the advice of the roadside sign we had seen advertising the show, as this was an activity that not many tourists knew about. If you’re looking for some evening entertainment in Woodstock, I recommend seeing what the Woolen Mill Comedy Club has scheduled during your stay.

Visit Billings Farm and Museum

A working farm and informative exhibition, Billings Farm and Museum provides a space for visitors to learn more about the settlement’s history. After paying for admission, guests are free to wander the premises, including the 1890 Farm House, which holds a variety of artifacts and the home’s original stove and oven that is still used to create modest recipes to this day.

After learning more about the farm’s original owners, guests can walk through the barns and pastures to admire the Jersey dairy cows, sheep, horses, chickens, and more.

Sample Maple Syrup at Sugarbush Farm

Get a real taste of Vermont’s pride and joy by visiting Sugarbush Farm, which offers samples of Pure Vermont maple syrup and aged cheeses at no cost. During your fall weekend in Woodstock, I highly recommend embarking on the property’s free Maple Walk to see how sap is extracted from trees to make one of our favorite pancake toppings. 

The farm’s Sugar House also provides commentary on the syrup production process through a family-produced video and informative handouts for visitors’ enjoyment. After learning about what it takes to create this sweet delicacy, consider purchasing a bottle to take home in order to support the farm’s ongoing efforts and impress your next brunch guests.

Take Photos at Sleepy Hollow Farm

On your way back into town from Sugarbush Farm, make a quick stop at Sleepy Hollow Farm for a swift photo. This privately-owned property has become the inspiration for many photographers in this day and age, especially when the foliage is at its peak. It is asked that visitors respect the residents’ privacy and refrain from trespassing while visiting, so it is encouraged to keep your visit short and sweet. Nonetheless, the farmhouse resting in a valley surrounded by golden trees is a sight that is most beautiful during a fall weekend in Woodstock.

Hike Deer Leap Trail

During a weekend of sampling maple syrup and consuming comfort foods, physical activity is often the last thing on one’s mind. However, one of the best things to do in the fall in Woodstock is to admire the foliage, which is often best experienced by a high vantage point. There are a few different trails to choose from, but I recommend driving around 30 minutes into the Killington area to Deer Leap Trail, a masked footpath that leads to a gorgeous overlook. While most of the leaves had already fallen by the time I visited, all I could think about from this height was what the surroundings would have looked like at their peak.

Where to Stay Near Woodstock, Vermont

If You Want to Save: The Mountain Inn at Killington

All I wanted to celebrate fall was a comfortable and homely stay in New England, and The Mountain Inn at Killington definitely delivered. Although it is about a 20-30 minute drive from downtown Woodstock, this affordable and welcoming hotel in Killington’s mountain range provided us with a quintessential stay during our extended weekend in the area.

Situated outside of the hotel’s entrance are two model ski gondolas and a handful of benches, greeting visitors returning from a day of skiing or exploring the town. The hotel staff was friendly and willing to accommodate our requests, and they even served a daily complimentary breakfast that fueled us for the day ahead. Even if Killington wasn’t on your bucket list, per se, this hospitable inn is reason enough to stay in the area.

If You Want to Splurge: Woodstock Inn and Resort

While this was galaxies away from my budget’s limits, the Woodstock Inn and Resort is an elegant choice for those willing and able to splurge. Located in downtown Woodstock, this sophisticated structure has become a landmark of the town. My friend and I admired the great lawn in front of the property, joining the others who were doing some leisurely reading and conversing on the lawn’s chairs.

Some light exploring inside the hotel revealed a grand fireplace, chess tables, and an abundance of snug reading spots romanticizing Woodstock’s slower pace of living.

A fall weekend in Woodstock provides the perfect excuse to indulge in a laidback weekend of reading, brunching, and leaf-peeping. See for yourself why Woodstock ranks so highly on travelers’ bucket lists by visiting when the town is cloaked with gleaming leaves.

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