Woodstock, VT Fall Itinerary

By Kelley Boymer
3 Oct 2023

photography by craig mackay

Fall Decorating Ideas For Your Home

Fall is one of the most popular times to visit Woodstock, Vermont, and for good reason! Our charming little village, is your quintessential New England small town with quaint shops, seasonal farm-to-table dining, scenic drives along country roads, hikes with panoramic views of sweeping fall hues and so much more. Woodstock, Vermont is the perfect fall getaway for both adventure and rejuvenation. With everything from relaxing spa treatments to exhilarating mountain biking–Woodstock has a little bit of something for everyone.

Today we are sharing a 2-day fall itinerary to make the most out of your Woodstock vacation! Whether you are in town for a weekend or mid-week stay we are giving you the very best of our small little town.

You might also like: Where to eat in Woodstock and Woodstock, VT fall bucket list.

Our complete guide to your perfect 2-day trip to Woodstock during the fall season.

Woodstock, VT Fall Itinerary

the woodstock inn during the fall season


The Woodstock Inn

The Woodstock Inn (book with this link for 10% off your stay) is one of our favorite spots to stay in Woodstock. Not only is it conveniently located right in the village within short walking distance of all the downtown shopping and dining, but it’s a beautiful hotel with great amenities, dining options and beautiful rooms. The spa is not to be missed!

506 On the River Inn

506 On The River Inn is a great family friendly stay just outside of the village. There is an indoor pool, game room and in-house restaurant for the whole family to enjoy.

Sleep Woodstock

For those looking to prioritize the adventure and outings over the stay, Sleep Woodstock is a perfect budget friendly option. Simple, clean and reliable– Sleep Woodstock gives you a place to lay your head without all the frills.

Woodstock Vermont Downtown in Fall | Click. Read. Love. 10.15.21

Day One

Morning and breakfast

  • For one of the best breakfasts in town, head to Mon Vert Cafe. Located in the heart of the village, Mon Vert has both dine in and to go options with delicious baked goods, coffee and yummy meals such as our favorite breakfast burrito and “challa” French toast.
  • If you’re staying at the Woodstock Inn and looking for something convenient and delicious, check out the breakfast buffet at The Red Rooster.

daytime exploring

  • Begin your stay in Woodstock with a beautiful, scenic stroll through the village. Begin by walking down Central Street, browsing the shops on either side. Some of our favorites include: Woody’s, Elevation Clothing, 37th Central Clothiers, Red Wagon Toy Co. and Yankee Bookshop. Loop back to check out Elm Street– don’t miss Clover Gift Shop and F.H. Gillingham & Sons. Continue down Elm and cross the iron bridge taking a left to walk down River Road and Mountain Ave. you’ll pass beautiful Faulkner Park. Loop back into town by crossing the Middle Covered Bridge.
  • Kid friendly: For a family friendly morning, head to Vail Field to play on the playground complete with fields to run and play soccer, basketball and tennis courts, play structures and swings.
  • Rainy day option: On those overcast and rainy days, bring your kids to swim at the Woodstock Athletic Club indoor pool.
The Best Takeout In Woodstock, VT
the village butcher


  • For lunch, head to one of our favorites– The Village Butcher. Get a delicious and fresh made sandwich with local meats, cheeses and produce. Take your sandwich down by the river, behind the Woodstock History Center just a few buildings down from the Butcher. Enjoy a nice picnic riverside, taking in the beautiful views.
  • If you’re looking for a more formal lunch, head to Sante (open for lunch noon-3pm Friday & Saturday). Sante serves small bites and entrees prepared using local, seasonal foods and has an exquisite menu. Treat yourself to one of their delicious margaritas!
  • For an afternoon sweet treat, head to Woodstock Scoops for their famous seasonal favorites maple creemee and pumpkin flavors.
the barnard general store

afternoon exploring

  • Spend your afternoon enjoying a beautiful scenic drive along Vermont dirt roads. Drive just a few minutes outside the village for a plethora of scenic routes that will provide the most beautiful landscapes and views. Here’s a few options:
    • VERMONT ROUTE 12: Take a drive south on Vermont Route 12 to explore the countryside dotted with picturesque farms and open meadows. This route passes through charming towns like Barnard, Bethel, and Randolph, offering a quintessential Vermont experience. Stop at the Barnard General Store for breakfast, lunch or ice cream and Silver Lake for a refreshing dip during the summer or a walk around the lake during the fall.
    • POMFRET LOOP: If you are looking for a drive that brings you through classic Vermont backroads, head east from Woodstock on Pomfret Road to embark on a delightful 18-mile loop drive through the rural beauty of Pomfret. This scenic drive takes you through rolling hills, past historic farms, and along the shores of picturesque Silver Lake.
    • OLD RIVER ROAD: Head north on Route 12 out of the village of Woodstock and turn right at Billings Farm and Museum onto Old River Road. Follow the dirt road along the meandering Ottauquechee River past scenic homes, farms and rolling hills. You can continue until the Taftsville Bridge and cross the bridge looping back to Woodstock or continue through until the Simon Pearce Mill in Quechee and cross the covered bridge directly after the Simon Pearce store on your right to loop back to the village of Woodstock on Route 4. Stop at Simon Pearce for lunch, views of the falls, some glassware, pottery or an up-close look at glassblowing.
  • If you’d like to take in the sights on foot, head to one of our favorite local mountains for a gorgeous hike amongst the foliage: Mt. Tom or Mt. Peg. Both hikes are mild to moderate in ability level but Mt. Tom is longer. For a shorter version you can walk through Billings National Park to the Pogue for stunning foliage views. Mt. Peg is great for little hikers and families. Although the hike is fairly quick, the view is just as spectacular, especially during fall foliage! For more hiking recs and info head to our post on the best hikes in Woodstock.
Jess Ann Kirby shares her favorite places to stay, eat and shop in Woodstock, Vermont
foliage on old river road


  • If we were to choose one place to enjoy dinner while in town, it would be at Cloudland Farm in Pomfret. This working farm has a beautiful on-site restaurant that overlooks picturesque rolling hills. Bundle up and enjoy your dinner out on the porch to take in the gorgeous views. Enjoy a farm-to-table meal with delicious seasonal offerings and an ever-changing menu, that’s always delicious. They require reservations so plan ahead!
  • If you are looking for something right in the village, try another local favorite- The Prince & The Pauper. The Prince and the Pauper is romantic, intimate and classic, and creates stunningly delicious dishes. Enjoy!

Day Two


  • Start your morning with a delicious, no frills diner breakfast at The Mountain Creamery, located just a few minutes outside of the village in West Woodstock. If you are staying at Sleep Woodstock you can simply walk next door and grab a bite to eat.
  • If you’re looking to grab and go, get a yummy breakfast sandwich from The Village Butcher. Then take a short drive out of town to Abracadabra— completely worth it for the best coffee in town!

daytime exploring

  • If you’re in the mood for some retail therapy take a walk through the village and check out some of our favorite shops.
  • Get your morning going with an exhilarating mountain bike ride at one of our local trails. Check out our guide for the best mountain biking in the area! For those looking for a more leisurely and scenic ride, check out Woodstock Wheels Bike Rental for e-bike rentals and local scenic routes to see the very best of the area.
  • Family friendly: For something the whole family will enjoy, head to Billings Farm & Museum for a true farm experience. Meet the cows and goats, enjoy animal and food programs and grab a bite to eat at the MOOveable Feast Food Truck and delicious seasonal sweets from the Farmhouse Scoop Shop.
yankee book shop Click. Read. Love. 10.7.22


  • For a sit down lunch, head back to Mon Vert for their delicious soups, sandwiches and salads. Dine al fresco on the patio or take your sandwich to go.
  • Grab and Go: For something quicker on the go, grab pre-made sandwiches from the Woodstock Farmer’s Market. “Moonlight in Vermont” with fresh apples, Vermont cheddar and turkey is our personal favorite for fall!

Afternoon Exploring

  • Wind down your 2-day venture with an afternoon at the spa. Head to The Spa at the Woodstock Inn for luxurious treatments and amenities. Enjoy the eucalyptus steam room, sauna and spa while you wait for your facial, massage or pedicure.
  • If you’d like to get out of town and explore a bit, head to Quechee just a 15 minute drive outside the village. Watch glassblowing at Simon Pearce, check out epic views from the Quechee Gorge in Quechee State Park, and stop at the Quechee Gorge Village for lots of Vermont made gifts and souvenirs.


  • Grab a fall signature cocktail from Au Comptoir, a quaint village cocktail bar located just off of Central Street in downtown Woodstock.
  • After a cocktail at Au Comptoir, head to Sante for delicious small bites and entrees using local, seasonal foods. Enjoy the intimate atmosphere and take your time enjoying your meal.
  • Family friendly: Worthy Kitchen is a great kid-friendly option for the whole family to enjoy. With everything from Mac-n-cheese, to burgers, fries, salads and a large array of beers on tap– you won’t be disappointed!
the bar at au comptoir

Fall Weather in Woodstock

Fall weather in Vermont typically cools down and averages in the 50s and 60s but can also reach highs in the mid 70s and lows in the 40s. The range in temperatures from morning to late afternoon can vary pretty drastically. Packing in layers is key for a successful Vermont fall vacation. Fall days in Vermont are usually spent wearing pants, t-shirts, long sleeves and light sweaters or jackets but evenings cool down and you will want to have a warmer fleece or heavier coat to keep you warm if you are outside.

Some outfit ideas: here, here, here and here.

Fall Packing List for Woodstock, Vermont:

  • Pants
  • T-shirts and long sleeves
  • Sneakers/hiking boots/waterproof boots
  • Socks/undergarments
  • Boots (Blundstones/suede booties)
  • Sweater
  • Jacket (raincoat/light jacket/heavy coat)
  • Scarf/hat
  • Bag

Getting to Woodstock

Once in Woodstock, the village as a whole is fairly walkable, and many visitors also get around via bikes. Car transportation is preferable, convenient and parking is typically easier to find.

If you are flying, it will be necessary to rent a car.

Uber/Lyft/taxi’s are not accessible in Woodstock. If you are staying in the village you will be able to walk to and from meals and excursions in town. If you stay at the Woodstock Inn & Resort there are transportation services available. Speak with the concierge to make plans prior to your arrival.


The closest airport and most convenient is Lebanon Municipal Airport. It is located about 20 minutes from Woodstock. This is a small airport, flying small planes and flights and connections are limited.

Burlington International is approximately 1.5 hours from Woodstock. This airport is usually less crowded and easier to navigate than Boston.

Boston Logan is approximately 2.5 hours from Woodstock depending on traffic.


The Dartmouth Coach is a great way to travel if you need transportation from the Boston Airport or another New England City. With destinations to New York City, Boston South Station, Hanover and Lebanon this is an easy and affordable travel option.


The AMTRAK train takes passengers from D.C. and NYC to White River, Vermont about 15 minutes outside of the Woodstock village.


It is fairly easy to walk most places while in Woodstock, but it does help to have a car if possible, especially for colder months. Vermont is a remote location and things are much more spread out than in cities and suburban towns. Many of our favorite recommendations include a drive out of town from 10-30 minutes. There’s metered parking throughout the village available on most streets. If you get a ticket remember to have a local business validate it for you and you don’t have to pay!

A 2-day trip to Woodstock, Vermont is the perfect way to get a taste of this charming, quintessential town and fall season is the most ideal time to enjoy the gorgeous weather and colors of the season. You can’t go wrong with a trip to Woodstock, Vermont during the fall!

Disclosure: if you buy something through the links on this blog, we may earn an affiliate commission. We only feature products we would personally recommend. Thank you for your support.

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  1. Terrey Rames wrote:

    Would you say the beginning, middle or end of October is best for fall color in Woodstock, VT? When were these pictures taken?

    11.19.23 | Reply
  2. Julia Felix Didier wrote:

    Hi, i am looking to drive in Woodstock this fall and loved your tour recommendations. do you have more in detail the 18 miles loop?
    POMFRET LOOP: If you are looking for a drive that brings you through classic Vermont backroads, head east from Woodstock on Pomfret Road to embark on a delightful 18-mile loop drive through the rural beauty of Pomfret. This scenic drive takes you through rolling hills, past historic farms, and along the shores of picturesque Silver Lake.


    3.8.24 | Reply

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