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HomeLife StyleWoodstock, Vermont Fall Itinerary | Jesse Ann Kirby

Woodstock, Vermont Fall Itinerary | Jesse Ann Kirby

Fall is one of the most popular times to visit Woodstock, Vermont, and for good reason! Our charming little village is a quintessential New England town, with quaint shops, Seasonal farm-to-table dining, take scenic drives along country roads, hike with sweeping panoramas of fall colors, and more. Woodstock, Vermont is the perfect fall getaway for adventure and rejuvenation. From relaxing spa treatments to exciting mountain biking, Woodstock has something for everyone.

Today we’re sharing a 2-day fall itinerary so you can make the most of your Woodstock vacation! Whether you’re in town for the weekend or a midweek stay, we’ll offer you the best accommodation in our town.

We’ve got your complete guide to the perfect two-day trip to Woodstock in the fall.

Woodstock, Vermont Fall Itinerary

Woodstock Inn in Autumn


Woodstock Inn

Woodstock Inn (Book through this link to get 10% off your stay) is one of our favorite places to stay in Woodstock. Not only is it conveniently located in the village and within walking distance of all city center shopping and dining, but it’s a beautiful hotel with great facilities, dining options and beautiful rooms. The spa is not to be missed!

506 River Inn

Riverside Inn No. 506 Located just outside the village, it is suitable for families. The hotel features an indoor pool, game room and on-site restaurant for the whole family.

Sleeping Woodstock

Sleep Inn Woodstock is a perfect budget-friendly option for those who wish to prioritize adventure and outings over accommodation. Simple, clean and reliable – Sleep Woodstock offers you a place to rest without any frills.

Fall in downtown Woodstock, Vermont | Click. read. like.  21.10.15

first day

morning and breakfast

  • For one of the best breakfasts in town, head to Monvet Cafe. Located in the heart of the village, Mon Vert offers dine-in and takeout options, including delicious baked goods, coffee, and delicious meals like our favorite breakfast burritos and “challa” French toast.
  • If you’re staying at the Woodstock Inn and looking for convenient and delicious food, check out the following locations for the breakfast buffet: red rooster.

Explore during the day

  • Start your journey in Woodstock with a stroll through the picturesque village. Start by walking along Central Avenue and browsing the shops on both sides. Some of our favorites include: Woody’s, altitude clothing, 37 Central Clothing Store, Red Wagon Toys Company and yankee bookstore.Take a look back at Elm Street—don’t miss it Clover Gift Shop and Gillingham & Sons. Continue on Elm, cross the iron bridge, turn left and walk along River Road and Mountain Ave. You’ll pass through beautiful Faulkner Park. Cross the central corridor bridge and circle back to the town.
  • Child friendly: For a family-friendly morning, head to Vail Field to play in the playground, which features running, soccer, basketball and tennis courts, play structures and swings.
  • Rainy day options: On a rainy day, take your children to swim. woodstock athletic club indoor swimming pool.


  • For lunch, head to one of our favorite restaurants – country butcher. Enjoy delicious fresh sandwiches made with local meats, cheeses and produce. Take your sandwich to the river, behind the Woodstock Historical Center and just a few buildings away from the Butcher Shop. Enjoy a picnic by the river and take in the beautiful views.
  • If you’re looking for a more formal lunch, head to Sant (Lunch is served Friday and Saturday from noon to 3 p.m.). The Sante restaurant serves an exquisite menu of snacks and main dishes prepared with local, seasonal produce. Treat yourself to a delicious margarita!
  • For an afternoon dessert, head to Woodstock spoon Known for its famous seasonal favorites maple cream and pumpkin flavors.
Best Take Out Restaurants in Woodstock, VT
The village butcher

Afternoon exploration

  • Spend an afternoon driving along Vermont’s dirt roads and taking in the beautiful scenery. Just a few minutes drive out of the village you can access numerous scenic routes to enjoy some of the most beautiful landscapes and views. There are several options here:
    • Vermont Route 12: Drive south on Vermont Route 12 and explore the countryside filled with picturesque farms and open meadows. This route offers a quintessential Vermont experience through the charming towns of Barnard, Bethel, and Randolph.Stopped at Barnard’s Grocery Breakfast, lunch or ice cream silver lake You can take a refreshing dip in the summer and take a walk by the lake in the fall.
    • pomfret trap: If you’re looking for a driving route through classic Vermont back roads, head east on Pomfret Road from Woodstock for a delightful 18-mile loop. Travel through the beautiful countryside of Pomfret.This scenic drive takes you through rolling hills, past historic farms and along the picturesque coast silver lake.
    • Jiuhe Road: From the village of Woodstock, drive north on Route 12 and turn right onto Old River Road at Billings Farm and Museum. Drive along the winding dirt roads of the Ottauquechee River, past scenic homes, farms and rolling hills.You can continue on to the Taftsville Bridge and loop back to Woodstock, or continue on to the Simon Pearce Mill in Quechee, at Directly across the covered bridge behind the Simon Pearce store on the right, looping back to the village of Woodstock on Route 4. Park at Simon Pearce At lunch, enjoy the view of the falls, enjoy some glassware, pottery or watch glass blowing up close.
  • If you want to see the sights on foot, head to one of our favorite local mountains for a gorgeous hike among the foliage: Mount Tom or Mount Peg. Ability levels for both hikes are light to moderate, but Mount Tom is longer. Mount Peg is great for small hikers and families. While the hike is fairly quick, the views are just as spectacular, especially during the fall foliage!For more hiking advice and information, head to our post Best Hiking Tours in Woodstock.
Jess Ann Kirby shares her favorite places to stay, eat and shop in Woodstock, Vermont
Leaves on the old river road


  • If I were to choose one place to have dinner in town it would be Yundi Farm In Pomfret. This working farm has a beautiful restaurant overlooking the picturesque rolling hills. Get dressed and enjoy dinner on the porch with the beautiful view. Enjoy farm-to-table cuisine featuring delicious seasonal produce and an ever-changing menu that’s always delicious.
  • If you’re looking for something suitable in the village, try another favorite – The Prince and the Beggar. The Prince and the Pauper is romantic, intimate, and classic, creating a stunningly delicious meal. enjoy!

the next day


  • Start your day right with a delicious, simple breakfast mountain dairy, just minutes from the village of West Woodstock. If you stay at the Sleep Woodstock Hotel, you can walk next door and grab a bite to eat.
  • If you want to grab and go, you can buy delicious breakfast sandwiches here country butcher.Then it’s a short drive out of the city. nonsense—Totally worth it for the best coffee in town!

Explore during the day

  • If you want some retail therapy, take a walk around the village and see Some of our favorite stores.
  • Start your morning with an exciting mountain bike ride on one of our local trails.take a look at our Your guide to the best mountain biking in the area!For those looking for a more leisurely and scenic ride, check out Woodstock Wheels Bike Rental E-bike rentals and local scenic routes are available to take in the best views in the area.
  • Family Friendly: For activities the whole family will love, head to Billings Farm and Museum A true farm experience. Meet the cows and goats, enjoy animal and food shows, and grab a bite to eat at the MOOveable Feast food truck and purchase delicious seasonal sweets from the Farmhouse Scoop Shop.
Yankee Bookstore Spot. read. like.  10.7.22


  • To sit down for lunch, please return my green Enjoy delicious soups, sandwiches and salads. You can enjoy al fresco dining on the terrace or take away sandwiches.
  • Grab and go: If you want a quicker bite to eat on the go, buy pre-made sandwiches from the store. Woodstock Farmers Market. “Vermont Moonshine” with fresh apples, Vermont cheddar cheese, and turkey is our personal fall favorite!

Afternoon exploration

  • End your 2-day adventure with an afternoon at the spa.Go to Woodstock Hotel Spa Enjoy luxurious treatments and amenities. While waiting for your facial, massage or pedicure, you can enjoy the eucalyptus steam bath, sauna and spa.
  • If you want to get out of town and explore, Quechee is a 15-minute drive outside the village.Watch glass blowing Simon Pearceenjoy stunning views of Quechee Gorge Quechee State Parkand stop at Quechee Canyon Village for many Vermont-made gifts and souvenirs.


  • Enjoy a signature fall cocktail over the countera quaint country cocktail bar located off Center Street in downtown Woodstock.
  • After a cocktail at Au Comptoir, head to Sant Enjoy delicious snacks and entrees made with local, seasonal ingredients. Enjoy the intimate atmosphere and take your time with your meal.
  • Family Friendly: Worth the kitchen A kid-friendly option for the whole family to enjoy. There’s everything from mac and cheese to burgers, fries, salads and plenty of beer on tap – you won’t be disappointed!
bar counter

Heading to Woodstock

Once you arrive at Woodstock, the entire village is fairly walkable, and many visitors also explore by bicycle. Car transportation is preferable, convenient, and often easier to find parking.

If you’re flying, you’ll need to rent a car.

Uber/Lyft/Taxi are not available in Woodstock. If you stay in the village, you can walk to and from the town for meals and tours. If you stay at the Woodstock Inn & Resort, you can take advantage of transportation services. Contact the concierge before your arrival to make plans.


The closest and most convenient airport is Lebanon Municipal Airport. About 20 minutes from Woodstock. It is a small airport that flies small aircraft and has limited flights and transfers.

Burlington International is about a 1.5 hour drive from Woodstock. This airport is generally less crowded and easier to navigate than Boston Airport.

Boston Logan is approximately a 2.5 hour drive from Woodstock, depending on traffic.

the bus

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


AMTRAK trains carry passengers from Washington, D.C., and New York City to White River, Vermont, about 15 minutes from Woodstock Village.


It’s fairly easy to get to most places on foot in Woodstock, but having a car does help if possible, especially in the colder months. Vermont is remote and things are more spread out than cities and suburban towns. Many of our favorite suggestions include driving 10 to 30 minutes out of town. Metered parking is available on most streets throughout the village. If you get tickets, remember to ask a local business to verify it for you so you don’t have to pay!

A 2-day trip to Woodstock, Vermont is the perfect way to see this charming, quintessential town, and fall is the perfect time to enjoy the gorgeous weather and colors. You can’t go wrong with a trip to Woodstock, Vermont in the fall!

Disclosure: If you purchase something through links on this blog, we may earn an affiliate commission. We only recommend products that we personally recommend. thank you for your support.

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