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10 Perfect Things to do in Woodstock, Vermont in the Fall

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There are no shortages of utterly charming villages in New England —  Norman Rockwell-esque towns that are beautiful in every season. And in the fall, when nature’s colors give an extra boost to every red barn and covered bridge and add highlights to every tall-steepled church, well that, my friends, is why visitors flock to Quechee and Woodstock, Vermont

These side-by-side villages and the surrounding farms, mountains, and valleys are a leaf-peeper’s paradise. As you ogle the blazing colors that surround you, why not sample incredible Vermont cheese, stroll across a covered bridge, visit Vermont’s only national park, walk through the treetops, and hike through the mountains? After all, that’s what autumn in Vermont is all about!

downtown Woodstock VT
Woodstock, VT

This is a local’s guide to the best things to do in Woodstock, Vermont, as well as the neighboring village of Quechee. We’ve included our favorite tourist attractions, places to stay, and of course, our favorite hiking trails — because we obviously can’t talk about things to do in fall without mentioning our favorite autumn activity. 

Ready to visit one of Vermont’s most lovely towns? Here we go.

Exploring Woodstock and Quechee, Vermont: The Details

Before we dig into all the incredible things to do in this part of Vermont, let’s talk details and logistics. Here are a few crucial pieces of information that will help you plan your trip to Woodstock and Quechee.

When is the Best Time of Year to Visit Woodstock, Vermont?

A split-rail fence along a farm field in Woodstock VT in the fall.
Woodstock, VT in the fall

That’s the million-dollar question, isn’t it? We have explored Woodstock and Quechee in every season, and I’m going to vote for October. The fall foliage season is EPIC, full stop. If you haven’t experienced a Vermont fall, it’s time to make amends. 

Fall-foliage in Woodstock, Vermont doesn’t happen like clockwork from year to year, but you can expect great colors from the end of September until the third week of October, give or take a few days. 

If you are planning a fall trip to Woodstock, starting early is crucial! Woodstock in the fall is popular and crowded. Reserve your Woodstock lodging six months in advance for the best selection, and if you want to avoid crowds during your visit, plan to visit during the early part of the week.

Woodstock in the summer is full of outdoor eateries, farm stands, and swimming holes. It’s our 2nd favorite time to visit. In the winter, you can hop on a horse-drawn sleigh, sip mulled cider as the snow falls gently past your window, and take some serious adventures on snowshoes and cross-country skis. The trails around Woodstock are a snow lover’s paradise!

How to get to Woodstock, Vermont

Half the fun of a Woodstock, Vermont vacation is the road trip to get there. The closest major airport is Burlington International Airport (BTV), which is 86 miles away. From there, you can rent a car, and embark on the New England road trip you’ve been dreaming about. 

Burlington is 100% worth exploring if you have time. This is Vermont’s largest city, and a great spot for shopping, dining, and lake-based activities. The foliage will peak a bit later in the Champlain Valley, so hit it on your way back if the leaf-peeping season is underway.

 The capital city of Montpelier also makes for a fun visit, with its gilded dome that sits atop one of the oldest and best-preserved state capitols in the nation. It’s about halfway between Burlington and Woodstock. The drive from Burlington to Woodstock is less than two hours, whether you choose to lodge in Woodstock or nearby Quechee (more on lodging in a bit). 

How Long Should You Stay in Woodstock, Vermont?

You can cram lots of fun into a single fall weekend in Woodstock, but I think four days is the sweet spot. Plan on a day in Quechee and a few in Woodstock. The towns are right next to each other, so you can drive back and forth between the two very easily. If you are into shopping and/or antiquing, you can easily spend a full day exploring all the shops in Woodstock and the Antique Mall in Quechee, so plan accordingly. 

Packing Tips for a Fall Weekend in Woodstock, Vermont

Vermont is delightful in that it embraces all four seasons with glee — sometimes all in the same week! Because many of our recommendations involve getting outside and enjoying the crisp fall air, frolicking with farm animals, and crunching leaves under your boots, I thought I’d share some of our favorite apparel and gear for getting outside in the fall. 

  • Wool layers – Merino wool is a magical fabric. You can wear it for days without having to wash it (no funk!), it wicks away sweat, keeps you cool in the summer and warm in the winter, and dries incredibly fast. I get almost all of my merino wool clothing from Woolx, which is based in Upstate New York. For your fall trip to Woodstock, I’d recommend a lightweight long-sleeve wool top (like the Remi), this Savannah wool vest, and the Brinley wool jacket. These layers represent all the best things about fall!
  • Hiking pants that don’t look like hiking pants – Yes, you’ll be spending a lot of time outdoors, but you want pants that can take you from trail to tavern without looking frumpy. During my recent trip, I wore these Halle Hiking Pants from Prana, which come in lots of colors and short sizes with a 30” inseam. They were perfect for my fall weekend. 
  • A chunky scarf or two – Scarves are always in fashion in Vermont. Here’s a colorful option and one that is a bit more muted. I love scarves! 
  • Wool socks – Warm toes are happy toes! I recommend getting a couple of pairs of wool socks from Darm Tough Vermont. They’re made in Vermont and unconditionally guaranteed for life. 
  • Hiking shoes – Sturdy footwear is a must for your trip to Woodstock. If you haven’t found your perfect pair of hiking shoes, now is the time to get fitted at your local shoe store. 
  • Thermos – You can’t have fall adventures without a thermos of something warm and delicious in your backpack, whether it’s a hot cider or hot soup. This unbreakable thermal bottle from Stanley gets the job done and easily fits in a purse or backpack. 

Psst… Looking for a printable itinerary for visiting Woodstock, Vermont in the summer and fall? This weekend itinerary includes our favorite hiking trails, historic sites, and restaurants, plus ideas for where to stay in Woodstock. Sign up for your free copy!


The Best Thing to do in Woodstock and Quechee, Vermont during the Fall

Now that we’ve covered all the necessities, let’s get to the fun stuff. Here are the best things to do in Woodstock and Quechee, Vermont during the fall foliage season. 

Frolic with Farm Animals at Billings Farm and Museum in Woodstock

A friendly cow at Billings Farm and Museum in Woodstock, Vermont.
This cow wants to be friends!

Farming roots run deep in Woodstock and the surrounding communities, and there’s no better way to experience life on the farm than at Billings Farm & Museum. Located just outside of the village of Woodstock, Billings Farm & Museum combines an award-winning jersey dairy farm with one of the finest outdoor history museums in the country. Not only can you meet more than 70 beautiful cows, but the farm is also home to goats, pigs, chickens, and five draft horses. 

Farm life exhibits are spread out across four historic barns and include displays featuring the seasonal activities that would have taken place on a Vermont hill farm more than 100 years ago. The exhibits tell the story of rural life in Vermont at the turn of the century. What was it like to cut ice from the pond, shop at the general store down the road, or boil down maple sap into sweet syrup? 

After exploring the exhibits, be sure to stop at the Museum Store and Dairy Bar, where you can sample award-winning Billings Farm Cheddar and eat your fill of Vermont-made Wilcox ice cream. 

Finally, be sure to meander around the pastures, orchards, and Heirloom Garden. Billings Farm & Museum is open every day except Wednesday from 10 am-4 pm until November 1, and select holiday weekends in the winter. Learn more at Billings Farm & Museum

Explore the Gardens and Hike the Trails at Marsh-Billings-Rockefeller National Historic Park in Woodstock

The main house at Marsh Billings Rockefeller National Historic Park in Woodstock VT
The main house in the fall

Right across the street from Billings Farm & Museum is Vermont’s only national park unit — Marsh-Billings-Rockefeller National Historic Park (that’s a mouthful!). Part nature preserve, part history museum, the national park service calls this unique park, “the only national park to tell the story of conservation history and the evolving nature of land stewardship in America.”  

The park is named for George Perkins Marsh, who developed an early philosophy of land stewardship which laid the foundation for the conservation movement in the United States between the 1830s and the 1860s. Frederick Billings bought the estate in 1869 and established a progressive dairy farm on the property. His granddaughter, Mary French Rockefeller, and her husband, Laurance S. Rockefeller, continued to develop sustainable farming and forestry practices when they took over the property. They established the Billings Farm & Museum in 1871 and donated the estate to the United States Government in 1992. 

The Pogue in Woodstock VT
Trail around the Pogue

During our recent visit, we were unable to tour the historic home, but there are miles and miles of trails that meander through the woods, past 400-year-old hemlocks, through pastures, and alongside rambling stone walls. If you only have time for one trail, I’d recommend the Pogue/Mt. Tom loop, which is 4.2 miles and gains 643 feet in elevation. 

A rainy day on the Pogue in Woodstock Vermont.
The Pogue in Woodstock

Trails at Marsh-Billings-Rockefeller National Historic Park are free to access and are open every day from dawn to dusk. Buildings are currently closed due to COVID-19 (2020). Use this Walk Woodstock trail map to explore all of the national park trails, as well as lots of others around Woodstock. 

Stroll through the Treetops at Vermont Institute of Natural Science (VINS) in Quechee

An arial view of the treetop canopy walk at VINS in Quechee Vermont
Aerial view: VINS Vermont

There are many reasons to visit the Vermont Institute of Natural Science in Quechee, Vermont — raptors, reptiles, and trails, but the coolest new feature is a forest canopy walk that lets you stroll through the treetops. The boardwalk is ADA-accessible and brings visitors 65 feet above the Ottauquechee River — eye-to-eye with the songbirds and squirrels that make their home in the forest. 

The attached treehouse brings visitors even higher into the canopy with a 360-degree view of the surrounding countryside. You’ll also find a giant, climbable spider web with three layers of netting and an open weave to see down to the forest floor. 

VINS is open every day from 10 am-5 pm with live bird programs at 11 am, 1:30 pm, and 3:30 pm. This is a great family-friendly activity for all ages. Unfortunately, pets are not permitted. 

Sample Mouth-Watering Cheeses at Sugarbush Farm in Woodstock

Two kids petting a calf at Sugarbush Farm in Woodstock, Vermont.
Sugarbush Farm. Photo credit: Betsy Luce

Looking for any excuse to sample some incredible Vermont cheeses? Me too! Not only is Sugarbush Farm one of the prettiest farms we’ve ever been to, but it’s also the maker of award-winning cheddar cheese and delightful maple syrup. 

Bring your camera and a picnic and plan on spending a few hours at Sugarbush Farm, which covers 550 acres. You are welcome to visit the sugar house, the cheese packing room, and the farm store. Visit with the cows, meander in the woods, and enjoy this little piece of Vermont heaven. 

Sugarbush Farm free to visit and is open every day except Thanksgiving and Christmas from 8 am-5 pm during the week and from 9 am-5 pm on weekends and holidays. For directions or to visit the online store, check out Sugarbush Farm

Hike the Quechee Gorge Trail along the Ottauquechee River in Quechee

Quechee Gorge as seen from the Route 4 bridge.
Quechee Gorge in the fall

Quechee Gorge is known as “Vermont’s little Grand Canyon” and at 165 feet, is the deepest gorge in Vermont. Because Quechee Gorge can be easily viewed from the Route 4 bridge, it is one of the most popular tourist spots in Vermont, attracting more than 200,000 visitors annually. 

The gorge is certainly beautiful, and worth stopping for a photo, but be prepared for throngs of people starting around 10 am and lasting well into the evening. In addition to viewing Quechee Gorge from the bridge, I recommend hiking the Quechee Gorge Trail, which isn’t quite as crowded as the bridge location. The trail is 2.7 miles (round trip) and gains 200 feet in elevation.

Inside Quechee Gorge

If you have time, park your car at the Quechee Visitor Center and walk across the street to Dewey’s Pond. This is a nice, level path that goes past the dam and out to a pond full of geese. The colors are lovely on a fall afternoon. 

When you get to the small parking area, turn around and retrace your steps, and then head down into the gorge. If you are short on time, skip Dewey’s Pond and just hike down to the gorge.

Quechee Gorge Trail descends through a forest of hemlock and mixed hardwoods, which are so pretty in the fall. There is a chain-link fence along the gorge to keep people from falling, but once you are down at river level, you can walk out onto the rocks along the river, and even go swimming if it’s not too cold. 

The Route 4 Bridge in Quechee, Vermont as seen from the bottom of Quechee Gorge
Route 4 Bridge from Quechee Gorge

There’s a little snack bar across from the gorge that serves ice cream, burgers, and fries — perfect for a post-hike snack. 

Visit a Covered Bridge or Two (or Six)

There are more covered bridges per square mile in Vermont than in any other state — more than 100! The Woodstock area has some incredibly beautiful covered bridges that are worth exploring. All of these historic covered bridges are within a 10-mile drive of Woodstock. Don’t forget your camera!

  • Middle Covered Bridge – Located right in downtown Woodstock on Mountain Avenue, Middle Covered Bridge spans the Ottauquechee River, and was constructed in 1969 using traditional materials and methods, including wooden pegs instead of nails. This lattice truss bridge is 139 feet across and probably the most photographed bridge in the area. Park your car in town and access Middle Covered Bridge on foot. 
Middle Covered Bridge in Woodstock, Vermont
Middle Covered Bridge, Woodstock
  • Taftsville Covered Bridge – Located east of Woodstock on Route 4, the Taftsville Covered Bridge is bright red and one of the oldest covered bridges in the nation (1836). At 189 feet, it is the second-longest covered bridge in Vermont. This was my favorite bridge to photograph during our recent visit. 
The Taftsville Covered Bridge in Woodstock, Vermont
Taftsville Covered Bridge, Woodstock
  • Quechee Covered Bridge – The sweeping views from the Quechee Covered Bridge are pretty phenomenal in every season. Located near the famous Simon Pearce Glassware store and restaurant, this beautiful bridge had to be rebuilt in 2012 after Hurricane Irene caused significant damage the year before. There is a small park and good parking nearby.
A black lab puppy poses in front of the Quechee Covered Bridge in Quechee, Vermont
The Quechee Covered Bridge, Quechee
  • Willard Covered Bridges – Located in North Hartland, Vermont (about 13 miles from Woodstock), these two bridges are connected by an island in the Ottauquechee River. The western bridge was built in 2001. The eastern bridge was built in 1870 and is listed on the National Register of Historic Places. You can take an easy trail down below the dam to get some great photos of the bridges and the river. 
  • Lincoln Covered Bridge – The Lincoln Covered Bridge is located on Route 4 in West Woodstock. It was built in 1877, and at the time it was the only known example of a Pratt truss design, featuring flanking arch trusses made of six laminated layers. 

Check out Simon Pearce for the View, the Food, or the Amazing Glassware

Simon Pearce Glassware in Quechee, Vermont
Simon Pearce in Quechee

Simon Pearce Glassware has been handcrafted in Quechee, Vermont since 1981. This beautiful spot on the Ottauquechee River (near the Quechee Covered Bridge) is powered by hydroelectricity and features the Simon Pearce flagship store and glass-blowing demonstration facility, showroom, and restaurant. 

During our recent visit, the glassblowing demonstrations were on hold (COVID), but the restaurant was open for both lunch and dinner. Simon Pearce was voted one of “America’s Most Romantic Restaurants” by Travel and Leisure Magazine. We had a light lunch, which was divine — Vermont cheddar soup and fresh greens, plus a sparkling one and chocolate mousse. The food and the view competed for our attention the whole time. Incredible.

Step Back in Time in Woodstock Village

A historic home in downtown Woodstock, Vermont surrounded by fall foliage.
Historic Woodstock, Vermont

With a plethora of historic buildings surrounding a central town green, a thoroughly walkable downtown, and picture-postcard scenes around every corner, is it any wonder that Woodstock has been named one of the most beautiful small towns in America over and over again? 

From downtown Woodstock, you can easily access Billings Farm and Museum, Marsh-Billings-Rockefeller National Historic Park, and Middle Covered Bridge. If you are a fan of historic architecture, be sure to spend time wandering around admiring the restored Georgian, Federal Style, and Greek Revival homes. The best way to explore Woodstock Village is to park your car downtown and simply explore. We found this visual history of Woodstock incredibly interesting and used it to help plan our downtown explorations. 

Shop ‘Til You Drop?

downtown Woodstock VT on a rainy day
Downtown Woodstock in the rain

Because I spend most of my discretionary dollars on traveling, I rarely have money left over for shopping. I do, however, love exploring some of the small, local shops in Woodstock and Quechee on a rainy day. 

In Woodstock, definitely check out F.H. Gillingham & Sons, an old-fashioned country store that has been in operation since 1886. You’ll find a little bit of everything inside, from hardware and sporting goods, to local cheese, toys, and fishing supplies. Some of our other favorites in Woodstock include the Clover Gift Shop, the Yankee Bookshop (I can’t resist a bookstore!), and Vermont Eclectic Company, Woodstock’s newest (and super unique) gift shop. 

In Quechee, I definitely recommend stopping at the Vermont Antique Mall, which is full to bursting with cool treasures, whether you’re into pottery, textiles, furniture, or old tools. The Vermont Antique Mall is 17,000 square feet of treasures, so be prepared to spend some time exploring. It’s open from 10 am-5 pm every day except Easter, Thanksgiving, Christmas, and New Year’s Day. 

Have a Picnic on Top of Mount Peg

The view from the top of Mt. Peg in Woodstock Vermont in the Fall.
The view from Mt. Peg in Woodstock

If you wake to a beautiful morning and just have to spend the day outdoors, grab some picnic food at Jake’s Quechee Market and hike the short trail to the top of Mount Peg. The trail begins in a residential area (parking for about three cars) and climbs through woods and fields to the summit of Mount Peg. It’s not a hard hike, and there are benches and a picnic table at the top. 

The views of Woodstock are fabulous, especially for such a short climb! Bring your camera and plan to spend some time at the top. When you’re ready to return to your car, take the Spruce Trail, which will lead you back into the woods and down the mountain. This was one of my favorite hikes of our weekend in Woodstock. I hiked up with my coffee and breakfast and it was so peaceful and beautiful!

Where to Eat in Woodstock and Quechee

The Skinny Pancake in Quechee, Vermont
The Skinny Pancake in Quechee

Need some suggestions for awesome eats in Woodstock and Quechee? Sampling all the local food options is one of our favorite pastimes. Here are our recommendations for some seriously good eats. Note: A food photographer I am not. You’ll have to check out these eateries based on my recommendations and not my sub-par photography, which I won’t include here.

  • Best place for ice cream: Vermont maple walnut ice cream at Mountain Creamery! This is the stuff dreams are made of. 
  • Best farm-fresh groceries: Jake’s Quechee Market has everything you need — local craft beer, farm-fresh meats and veggies, prepared foods, and even Vermont gifts. The location is great too!
  • Best breakfast in Quechee: The Skinny Pancake, right next to Jake’s Quechee Market on Route 4 in Quechee. The best crepes in Vermont. And real maple syrup, of course!
  • Best breakfast in Woodstock: For awesome coffee and locally-sourced food in a cool, relaxing space, pop into Mon Vert Cafe in Woodstock. Their breakfast burrito is so filling and so yummy!
  • Best fine dining: Simon Pearce in Quechee. It’s worth it for the views alone, but the dinner and lunch entrees are uniquely prepared, beautiful, and delicious. 
  • Best casual fare: Worthy Kitchen in Woodstock serves comfort foods like burgers, mac-and-cheese, and chicken wings, plus some delectable vegetarian options. The fries are a favorite treat!

Woodstock, VT Hotels and Airbnbs

Buddy's Airbnb in Quechee, Vermont
Buddy's Airbnb in Quechee, Vermont
Buddy's Airbnb in Quechee Vermont
Buddy's Airbnb in Quechee Vermont
Buddy's Airbnb in Quechee Vermont

There are a lot of unique accommodations in Woodstock and Quechee! Depending on when you book your hotel reservations, you may have to choose entirely based on what’s available, especially in the fall. Here are our top picks for places to stay in Woodstock and Quechee.

  • The Shire Hotel, Woodstock, VT – You can’t beat the downtown location of the Shire Hotel. It’s right on the river and within walking distance of all the best Woodstock attractions. Many of the rooms have a river view with a fireplace, and all of them include a fridge and free Wi-Fi. Bonus: there are dog-friendly rooms available! This is our favorite hotel in Woodstock, especially for couples! 
  • The Woodstocker, Woodstock, VT – Here’s another romantic choice for your Woodstock vacation. We especially love the country decor, clawfoot tubs, and breakfast at the Woodstocker. It’s quite an elegant place and worthy of a splurge! 
  • Buddy’s Airbnb, Quechee, VT – During our most recent stay, we chose an Airbnb in Quechee. We were looking for affordable, dog-friendly lodging, and we found it just a mile from Quechee Village. This little place is tastefully decorated and perfect if you want to cook your own meals. It’s close to all the Woodstock and Quechee attractions, and our pup, Malinda felt right at home. 
  • 1890 Condo, Woodstock, VT – Need a little more room to spread out? This in-town condo is just a short walk from the center of town. With three bedrooms and two bathrooms, this cozy space has room for six people. Pets are permitted too. We have not actually stayed here, but we’re eyeing it for our winter vacation. 

Have you ever explored Woodstock and Quechee, Vermont? What are your favorite things to do there?

Loren Spencer

Saturday 24th of July 2021

I want to relocate to Vermont so bad!

April

Friday 10th of September 2021

@Loren Spencer, same here! It seems amazing! We are really hoping to in a few years. I'm from the Ozarks originally and a lot of these pictures remind me of the autumns there.

Robbie Brown

Tuesday 9th of March 2021

Sugar Bush farm is the best. I have been there twice & will visit again. This California gal loves Vermont