A Fall Guide to Woodstock, Vermont

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Cruising through Vermont during fall foliage season has always been at the “peak” of my bucket list.  Although I live in Connecticut and enjoy gorgeous autumn colors here as well, the allure of the reds and oranges further north, and the promise of quintessential “Gilmore Girls” type towns, has always had me itching to plan a Vermont getaway.  As an added incentive, it was time for my husband and I to celebrate our 5 year anniversary — just the two of us!  Yippie!  Whether you have Woodstock on your must-visit list as an adult getaway, or instead as a family destination, you won’t be disappointed.  It’s a little town that packs a big punch of fun.  This fall guide to Woodstock includes everything you need to know about where to stay, places to eat, and nearby activities to fill your autumn weekend.

sleepy hallow farm - fall guide to woodstock VT
Table of Contents
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    For your Planning Purposes

    Getting there:  The closest airports are Boston, Manchester, Albany, and Portland.  Each airport is about 2-3 hours away.  For any New Yorkers itching to get out of town for some leaf peeping, you’re a 5 hour drive from the city, making it a great spot for a weekend getaway.

    Getting around: You’ll definitely need your own car, as there are limited taxis available.  While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots.

    When to visit:  Woodstock is lovely to visit all year round, but high season is September-October, when fall colors are at their peak. 

    Mainstreet in downtown Woodstock, VT
    Main Street in Woodstock, VT
    Wood covered bridge in Woodstock, VT

    What to do in Woodstock in the fall?

    Highlights if you're in a hurry!

    • Shop and stroll the town: Woodstock has that small “Gilmore Girls everyone-knows-each-other vibe.”  I love pocket- sized charming towns because it’s simply just impossible to go-go-go.  You’ll meander slowly through each shop, and before you know it, the whole morning will have passed!   

    • Photograph Sleepy Hollow Farm:  If you’re visiting Woodstock to photograph the fall colors, then take a drive to Sleepy Hollow Farm.  It has become quite famous on Instagram, but it’s worth checking out for yourself.  

    • Hike the Quechee Gorge: Hiking trails surround Woodstock and if you love the outdoors, you’ll love exploring the outskirts of town.   Quechee Gorge is a short 15 minute drive away, with an easy walking path down to the water.  Bring some snacks and enjoy the view!  

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    Interested in learning more about activities in Woodstock?  Check out this article to help plan your trip:

    View from the suspension bridge overlooking Quechee Gorge
    View of the Quechee Gorge from down on the water
    Historic house on Billings Farm
    Sleepy Hallow farm in Woodstock VT
    Playing in fall leaves

    Luxury Accomodations in Woodstock, VT

    My Pick

    • The Woodstock Inn and Resort is the famous hotel in town!  With a memorable “mini White House” entrance, cozy lodge, and beautifully appointed rooms, it has earned its top rank as one of the best hotels in New England.  It is walkable to town, has a heated pool (open seasonally), relaxing spa, tennis courts, and 2 restaurants on site. 
    Front lawn and entry way of Woodstock Inn

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    I Also Considered This Hotel

    • Jackson House Inn - This luxurious B&B is located right outside Woodstock and features some of the best breakfast spreads in town!  They offer both regular rooms and suite options, which overlook landscaped gardens.

    The Best Restaurants in Woodstock, VT

    Favorite spots

    • Before the town wakes up, walk over to Mon Vert Cafe for breakfast burritos, french toast, and a warm drink.  It’s one of the most popular spots in town, and by 9:30am there is a line out the door and down the street. 


    • At the end of the day, stop by Worthy Kitchen for a casual dinner that serves up comfort pub fare.  I loved the black bean veggie burger and mac and cheese.


    • If you prefer something a bit more fancy, the food at Simon Pearce Restaurant was delicious and elegant.  When making your reservation, request a table with views of the river.
    Street view of Mont Vert Cafe
    Challah French toast from Mont Vert cafe
    Aerial view of the lunch at Simon Pearce Restaurant

    Other Popular Restaurants

    • Cloudland Farm - I most regret not booking a table here!  Cloudland farm is a working farm, with spectacular views of the rolling hills of Vermont.  The menu changes daily and is a true farm-to-table dining experience.  


    • Kelly Way Gardens - If you’re visiting Woodstock in the summer months, reserve a dining experience at the off-site farm of the Woodstock Inn and Resort.  You can even arrange for guided tours and private tastings. 


    • 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.  


    • Village Butcher - The Village Butcher is the famous deli in town, offering a wide assortment of sandwiches and meals to- go.  It’s a great spot to pick up lunch before a hike.  If you’re a vegetarian you may be happy to learn that they are famous for making a delicious veggie option called the Veggie Lover’s Delight.

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    Would you like to learn more about my favorite spots to eat? 

    Tips for traveling to Woodstock, VT

    Close up view of a pumpkin in Woodstock VT
    • Peak fall colors are tricky to plan for, and extremely weather dependent:  It’s a little bit of luck of the draw when it comes to seeing the perfect autumn scene -- sometimes the brightest Vermont foliage arrives in September, and other years the colors brighten around mid October. A drought, or conversely, an overly wet season, can throw off the foliage by a few days, or even impact the amount of leaves on the trees.  Your best bet is to plan for an end of September or early October weekend.  No matter what, if you're visiting at this time of year it will be stunning.


    • Make your reservations early - especially for a fall getaway:  Woodstock is one of the most popular leaf peeping destinations in New England.  If it’s on your bucketlist, book your room now and don’t forget to make restaurant reservations as early as you can. 


    • Pack for warmth:  The October mornings in Woodstock are pretty chilly!  We experienced lows in the 50’s.  Bring a warm light jacket and chunky scarf weather.  

    That's a Wrap

    Woodstock is a must-stop on any VT road trip itinerary, and especially so during the autumn months.  I enjoyed my weekend away and would love to return for a longer fall foliage excursion throughout more of Vermont.  It’s a beautiful state with down-to-earth people and a laid back vibe that adds to its charm and appeal.

    I hope this article has inspired your fall getaway to Woodstock, Vermont.  If you have any questions, or your own travel tips, please leave them in the comments below.  Also, don't forget to sign up for the monthly newsletter, packed with travel tips, upcoming news, and access to FREE destination itineraries.

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