Visiting Woodstock, Vermont in Fall: Travel Guide

Are you Planning to Visit Woodstock, Vermont in Fall?? Then you’re at right place! There’s No better place to spend Autumn than in Vermont. Traveling through Vermont during fall foliage season is absolutely magical experience! The leaves are changing colors, festivities are in full swing, the air is crisp, and the town looks like something out of a Hallmark Movie! Read my list of best things to do in Woodstock Vermont in fall in this post!

Whether you are traveling with family or as a couple, you won’t be disappointed! The town is very charming and there is nothing like leaf peeping in New England! The fall foliage in Stowe and Woodstock is unreal. It’s something out of a Postcard Cover. I highly recommend it to visit if you loves autumn as much as I do. Crisp yellows, burnt oranges, and bright red wherever you go! 

Though the town is very small and compact, but it offers so many amazing things to keep you busy! If you’re in Woodstock, Vermont during Fall, you’ll love the farm fresh maple syrups, apple orchards, crisp air and bright red yellow colors around you! This is what I always loved about autumn season so much! And Woodstock, VT is perfect for fall weekend trip for the season! It’s charming and laid back town of Vermont!

This guide to visit Woodstock, Vermont in fall includes When to Visit Woodstock for best fall foliage scene, Where to Stay, best things to do in fall, activities to choose for your fall foliage trip, and what to know for your planning your Vermont fall trip!

Whether you’re stopping through on a road trip or planning a fall weekend in Woodstock, this guide will help you make the most of fall in Vermont’s most charming town!

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🍁 About Woodstock

Woodstock, Vermont was chartered in 1761. It’s an incredibly charming small town with preserved 19th century Victorian mansions, covered bridges and picturesque maple and cheese farms. The entire downtown area is on the National Register of Historic Places.

It was named “The Prettiest Small Town in America” by the Ladies Home Journal magazine, and it really lives up to that title. Walking around the downtown, you can’t help but feel like you’re in a postcard!

Woodstock is located in the center of Vermont, nestled in the Green Mountains. It’s a beautiful town that’s extremely photogenic especially in Fall. The river Ottauquechee, covered bridges, small farms and historic downtown makes it perfect charming New England Town to visit in Fall.

P.S. Looking to visit more cozy Vermont towns on your trip? Check out my 2-Day Stowe Fall Itinerary that pairs Woodstock for the ultimate fall weekend! 

🍁 Things to Know For Planning Your Woodstock Vermont Fall Weekend trip 🍁

✈️ How to Get to Woodstock, Vermont

The closest airports are Burlington, Vermont. It is widely connected by major US airports. Most of the people include Woodstock as a Part of their New England Fall Roadtrip, so you can start your trip from here in northern Vermont.

The best option for International travelers and people flying from big USA cities, your best bet is Boston Logan International Airport (BOS). Located in the city of Boston, Massachusetts, this large airport is the best place to start your search for flights from Europe and other worldwide destinations.

If you are living near New York State or New Jersey, it’s easy 5-6 hours drive for leaf peeping in the fall season, making it a great spot for a weekend getaway.

Also Note that Burlington Airport is very SMALL, so there can be limited availability for car rentals during Peak Fall Foliage season! So, make sure to book car rentals ahead of time when planning your trip! I highly recommend to arrive at Boston Airport for better car rental options!

🚗 Getting around Woodstock, Vermont In Fall

Woodstock town itself is walkable, and there are handful of sights in the main street. But most of the best things to do in Woodstock including hikes or sightseeing spots are reachable via drive. So, realistically, you’ll definitely need a car to visit Woodstock, VT in fall.

Public transportation in the New England region is very limited and taxis available in New England states are very expensive. 

Roads around Woodstock are in fantastic condition while parking is aplenty, so hiring a car and driving around this beautiful area is best. Check Car Rental Options here.

🍁 When is it peak fall foliage in Woodstock, Vermont?

It can vary quite a bit! There are plenty of websites that have predictors if you’re planning a trip. Sometimes it arrives at the end of September or other years in mid October. A drought, or an overly wet season, can affect the foliage, or even impact the color displays of leaves. 

This website will give you an idea of what dates were best for leaf-peeping last year. Usually anywhere between end September to early October week tends to get you stunning colors! This time of the year is always beautiful in Vermont!

🍁 How many days do you recommend for Woodstock, VT? 

Woodstock is small town. You can bike around the town and will be able to see the whole place yourself! But there are so many things to do here and visiting other nearby places. But definitely, you can see everything in 48 hours, so 2 days are enough to explore Woodstock, Vermont!

🍁 How far in advance do you recommend booking a fall foliage trip?

Seeing fall foliage is one of the best things to do in Woodstock, Vermont. So naturally, everyone flocks to Vermont during the fall season. Most of the Budget inns and bread and breakfasts places get booked many months in advance!

So if you’re serious, I suggest to book your trip almost 6 months in advance. This will guarantee you have a chance to get affordable accommodations. Keep in mind that Woodstock is really small, and there aren’t too many inns around.

Where to Stay in Woodstock, Vermont In Fall?

Hotels, guest houses, and inns are located in the town center of Woodstock as well as the surrounding area. If you stay in town, you can enjoy having the restaurants and amenities on your doorstep with no need to drive. Staying to nearby town center is perfect if you want more of a countryside vibe.

• Luxury: Woodstock Inn and Resort – It is the famous hotel in town!  With a memorable “mini White House” entrance, cozy lodge, and beautifully appointed rooms, it has earned as one of the best hotels in New England. It has a heated pool, relaxing spa, tennis courts, and 2 restaurants on site. 
• Mid Range: The Village Inn of Woodstock – This luxurious historic B&B is located right in the center of Woodstock and features some of the best breakfast spreads in town! They offer both standard and deluxe rooms which overlook landscaped gardens.
• Budget: The Shire Woodstock is best choice.

P.S If you’re planning to visit more charming towns in Vermont, Read my ultimate guide about Best areas to stay in Vermont in Fall here.

🍁 What to do in Woodstock, Vermont in Fall?

Though Woodstock is small and compact, there are so many beautiful places to visit around! From colorful covered bridges, farms, to state parks, it has many beautiful places to explore during fall season. Here are top things to do in Woodstock, Vermont in fall season.

Explore Woodstock Main Street and the Village Green

The small town center of Woodstock will give you Gilmore Girls vibes and its central street is heart of the town. This walkable center is bursting with cafes, restaurants, and small independent boutiques where you can pick up books, jewelry, and souvenirs. 

Wander the street, grab a maple latte or coffee from Mont Vert Cafe or Soulfully Good Coffee; it’s the perfect way to spend a autumn weekend morning in Vermont. Don’t forget to wander nearby Elm Street and Pleasant Street for its beautifully decorated Pumpkin houses with fall foliage!

Many of the houses and shops along the streets are decorated with fall wreaths, jack-o’-lanterns, scarecrows, and corn-stalks! You’ll feel like you’re actually in Halloween town.

If you love history, visit the Woodstock History Center on Central Street. You can see the artifacts on display including paintings, photographs, books, and objects. It’s a small collection but utterly worth a visit to understand more about the area.

TIP: Must come early to walk around! If you get here early, you’re more likely to get a good parking spot – without having to drive around for a while. Plan to be on foot for the rest of your stay in downtown because the spots are almost always full for the Parking!

Walk to Woodstock Middle Covered Bridge

Vermont and the whole of New England region are famous for their covered bridges. These historic structures were constructed during the 19th and 20th centuries on the river to provide safe shelter for pedestrians caught in storms. But today, they are used for vehicles.

The Woodstock Middle Covered Bridge is located over the Ottauquechee River and is one of the most beautiful bridges of its kind in Vermont. This bridge also has separate walkway for the pedestrians. This is one of the classic Woodstock VT attractions that you can visit in town without the need for a car. 

Check out the Woodstock Inn & Resort

During the holidays, this place is fully decked out with festive flowers and lots of pumpkins. Even if you aren’t staying here, it’s worth to visit the grounds ! This place is a beautiful sight to see on your stroll around the Village Green in Woodstock, VT.

Visit Woodstock Farmers Market

Woodstock Farmers Market is located one mile west of the town. It’s open Tuesday through Saturday (closed on Mondays and Sundays) and is attached to a seasonal garden center. It is more like grocery store than your typical local market that lined with vendors!

But it’s a lot of goods come from local farmers in the area and locally sourced ingredients.The market sells fresh grocery produce, dairy and eggs, meat and seafood, baked goods, and specialty pantry items. You also pick up pre-made artisanal sandwiches to go. This is great place to pick up your essentials before embarking on your Fall Foliage New England Roadtrip. 

Sample Maple Syrup at Sugarbush Farm

A cute little family-owned farm with 500 acres of land. They produces some of the best Vermont cheddar, maple syrup, and so much more. You can also walk the nature trail through the woodlands, and browse the farm shop!

They even have a maple syrup museum. You can see how cheese and Maple Syrup are made here plus the tastings! It’s free to visit but make sure to buy something to support their business.

Stop by Beautiful Jenne Road Farm

This farm is located a little outside of Woodstock, in Reading. It’s a bit more difficult to find, but here you’ll see cows roaming the land and an iconic red barn with mills! This working farm is owned by a local family and has been in operation since the early 20th century.

Unfortunately, You can’t visit inside but you are permitted to stop by for a quick photo. Plus, you can pick up some of their maple syrup while passing through. It is one of the most Instagrammable location of Woodstock to visit during fall when colors are changing behind the red buildings.

Explore Billings Park and Mount Tom

If you’re craving for outdoors, hike the Mount Tom. The hike starts from Billings Park – a large green space that also contains the Marsh-Billings-Rockefeller National Historical Park. There are multiple hiking trails and walking paths within this complex of varying difficulty.

You can reach at the Summit of Mount Tom via 4-miles RT moderate hike. At the top, you’ll get panoramic colorful views of Woodstock in fall season. It is one of the best places to visit in Woodstock, Vermont in fall during sunset.The trail is accessible between April and October before the snow arrives.

Visit the Billings Farm and Museum

Billings Farm and Museum is one last farm on your list of things to do in Woodstock Vermont that is a little different from the others. It’s very easy to visit from the downtown Woodstock, even without needing a car. This farm is known as one of the finest outdoor history museums in the country! And you can visit it with small fee.

Once you’re in, you can wander around the barns, pastures, tractor collection, kitchens, and 1890s farm manager’s lodge. And, of course, you can meet the resident animals. You can also watch their daily milking demonstration and see the dairy in operation. They also offers a many seasonal and special events throughout the year.

It’s a great place to visit with Kids for perfect fall foliage activity! They also have an ice cream shop on the premises.

Hike in Quechee Gorge State Park

Quechee is a small town located a 10-minute drive east of Woodstock. You can pick up hiking maps at the visitor center for hiking the gorge trails. You can opt for Queeche Gorge trail: a 2.7-mile roundtrip hike that offers beautiful fall foliage views.

The trail take you through the forest surrounding the gorge and provide different viewpoints of the natural wonder. Quechee State Park is one of the best things to do near Woodstock VT for outdoors lovers.

If you decide not to hike, just park up at the Quechee Gorge Bridge and take a look at the gorge known as Vermont’s “Little Grand Canyon”. The gorge looks stunning with all the fall foliage and definitely a must-do on my list of things to do in Woodstock, Vermont in fall.

You can also visit nearby Queeche Covered Bridge with little waterfall. Also take a look at Simon Pearce Restaurant & Glass Blowing Studio, perched above the waterfall! Go downstairs to the basement studio where you can watch the artisans blow glass into cups, vases, and more (all sold upstairs in the store!).

If you’re with kids, walk the Boardwalk at VINS Nature center, it gives best views of fall foliage without any kind of hiking!

Drive through Taftsville Covered Bridge

Another famous covered bridge of Vermont, Taftsville Covered Bridge is only a 5-minute drive east of Woodstock. This bridge is constructed over Ottauquechee River. It’s a vibrant red color with backdrop of orange and yellow trees makes it perfect place to see fall foliage near Woodstock, VT.

Constructed in 1836, the Taftsville Covered Bridge is actually one of the oldest of its kind in New England. You can drive beneath it in your car but it’s worth parking up and wandering down to the riverside where you can see the waterfall that drops below the bridge.

Eat the Maple Creme : Best things to do in Woodstock VT in Fall

Your trip to Woodstock, Vermont in Fall is incomplete without having Maple creme or soft ice cream! Visit the Mountain Creamery is a small, independently owned ice cream parlor located a short drive out of Woodstock VT.

All ice cream is handmade and uses local flavors from the Vermont region, such as maple syrup and walnuts. If you’re not a fan of ice cream, they also serve pies, smoothies, and frappes. 

But if you don’t want to drive, visit the Woodstock Scoops in Central street.

Explore Coolidge State Park

Vermont’s largest state park is located 12 miles (20 minutes drive) from Woodstock. Hiking trails in the Coolidge State Park navigate various peaks and lead you to dramatic views across the Black River Valley and the Green Mountains. The hiking trail here provides you the colorful display of autumn fall foliage views!

Coolidge State Park is known for its fantastic campgrounds so if you fancy spending a night in the wilderness while in Woodstock, this is the perfect place. There is a mix of campsites and RV hook-ups.

Ride the Green Mountain Railroad

Just located ~45 minutes outside of Woodstock, VT, this is a great way to see all the fall foliage! Guests of the Green Mountain Railroad enjoy a 2-hour trip through Vermont’s scenic countryside during September and October. Overlooking the mountains, rivers, and wildlife from the windows of the rail cars. This is one of the must do when in Woodstock, Vermont in Fall.

Taste the Local Vermont Cheese

If you like cheese, you’ll be love to visit the stores in Woodstock. The town is known for its cheeses and one of the top things to do in Woodstock VT is finding your favorite. 

I’ve already mentioned Billings Farm and the Woodstock Farmer’s Market which are two of the best places to try cheese in Woodstock. You can also visit Mac’s Woodstock Market, F. H. Gillingham & Sons on main street, and the Vermont Farmstead Cheese Company. 

Drive the scenic route RT 100, Vermont

Depending on how much the leaves have changed color, you can consider driving RT 100, one of the best scenic route known for fall foliage roadtrip in Vermont.

You can drive to Waterbury via Killington, and visit Ben & Jerry’s Ice Cream Factory or have fresh apple cider donuts at Cold Hollow Cider Mill. This makes just perfect day trip or you can continue your drive till charming town Stowe.

Where to eat in Woodstock, VT

• Mon Vert Cafe: This is one of the best places to eat in Woodstock, VT. Try their bakery items, breakfast burritos, French toast, or go for a lunch! Must try their Maple latte – it’s sweetened with real maple syrup, and it’s so warm and cozy! It’s one of the most popular spots in town, and by 9:30 AM there is a line out the door and down the street. So, go early when it opens !
• Worthy Kitchen: Make sure to make reservations; this place is always packed. They’ve got burgers, mac and cheese, and farm-fresh eats on the menu. Its great place to have your dinner. They also offers veggie baked bean burger!
• The Skinny Pancake: Located not far from the Quechee Start Park, this is a great place to stop by and grab breakfast/brunch on your way into Woodstock.
• Simon Pearce: If you prefer something a bit more fancy, then food at Simon Pearce Restaurant (Near Queeche Gorge) is also delicious and elegant. When making your reservation, request a table with the views of the river.
• Prince and the Pauper: Located in the heart of downtown Woodstock, the Prince and Pauper is another popular option for a good date night out in the town.
• Cloudland farm : Located near Woodstock, this is a working farm, with spectacular views of the rolling hills of Vermont. It looks stunning with fall foliage displays. Their menu changes daily and is a true farm-to-table dining experience. But make sure to book it in advance.

Tips for Visiting Woodstock, Vermont in Fall

• Make your reservations early during fall season:  Woodstock is one of the most popular leaf peeping destinations in New England. If it’s on your bucket list, book your room now and don’t forget to make restaurant reservations as early as you can. 
• Pack in layers:  The October mornings at this time of the year can be chilly! Also, rain is common at this time of the year! So, bring light fall sweaters and scarfs! Bring light rain jacket if rain is in forecast. It is always about right clothing than right weather!
• Check Peak Color Forecast of Past years: It’s a little bit of luck of the draw when it comes to seeing the perfect autumn colors! The colors can arrive as early as in September or in mid October. The weather and rain throughout the year can affect the peak colors and foliage predictions. So make sure to follow online websites before one month of your dates. So, be flexible in your plans a bit! But mostly end of September or early October weekend is best time to see fall colors in Woodstock, Vermont. No matter what, if you’re visiting at this time of year it will be stunning everywhere you go.

Conclusion

And that’s a wrap about fall in Woodstock, Vermont. Woodstock is a must-stop on any Vermont road trip itinerary, and especially during the autumn months. I really loved my roadtrip through Stowe and Woodstock. I wish to visit again someday for longer fall foliage excursion through Vermont. New England is my absolute favorite place in the world for fall foliage.

So, are you ready for pumpkin spice lattes, cozy sweaters, and spooky season?? Hope I inspire you to visit Woodstock, Vermont in Fall!

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