Woodstock, Vermont is one of those picturesque towns where you can find natural beauty and fun things to do year round, but I think autumn is when it is at its most gorgeous. If you’re looking for things to do in Woodstock VT in the fall, you’ve got so much to look forward to. Crisp autumn air, charming town festivals, and of course, fall foliage colors provide the most scenic backdrop. If you’re ready to plan your fall trip to Woodstock, Vermont trip then autumn fun awaits!
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Things to Do in Woodstock VT in the Fall
With natural beauty and small town charm Woodstock is one of the best fall destinations in the United States. Discover the best things to do in Woodstock on your next fall vacation.
Swing by Mon Vert Cafe for a Coffee
Mon Vert Cafe is one of the cutest cafes in Woodstock, Vermont with excellent coffee and delish menu options. This cafe definitely has a nice local Vermont feel, with locally sourced ingredients, a friendly staff, and a comfy, cozy vibe that’s perfect for a fall cup of coffee. They use Vermont Coffee Company grounds, so it’s hard to go wrong when you start with quality beans like that. Mon Vert Cafe is open for breakfast and lunch. Their French Toast is phenomenal!
Explore Downtown Woodstock
One of the most essential items on this list is to explore one of the most charming areas of Woodstock: downtown! There are a variety of great shops, bookstores, and restaurants, but one of the must visit spots is F.H. Gillingham & Sons. Gillingham’s General Store is one of Vermont’s oldest family owned general stores, and it’s been a staple of downtown Woodstock since 1886. You’ll find a little of everything (and a ton of great souvenir options) from clothing to maple syrup, to Vermont cheese and so much more. This is one of those places you really can’t skip over during a Woodstock trip and it also is the perfect place to pack a little picnic basket for your Woodstock explorations.
Take in the Fall Foliage Views from Mount Peg
Conveniently, the hike to the summit of Mount Peg begins right in the heart of Woodstock Village. Begining on Golf Street this is a 2.5 mile round trip hike it is a quick, somewhat steep trail. This isn’t a strenuous hike by any means, but you’ll be ready to relax and take in those views once you reach the summit. There also happens to be a picnic table and a few benches at the top, so you can comfortably enjoy your snacks from Gillingham’s while marveling at the panoramic views of Vermont fall foliage that stretch out beneath you. The rolling hills awash in autumn colors of gold and red are breathtaking from this vantage point, and this is a great spot for some fall foliage photography.
Go Apple Picking at Whitman Brook Orchard
Located in nearby Quechee, Whitman Brook Orchard is the perfect place near Woodstock to go pick your own apples. Apple picking is a quintessential fall activity for the region, and Whitman Brook Orchard has over 140 varieties of apples on this stunning property, and their “you pick” apple orchard is just waiting for you to come on out and explore.
Explore Sugarbush Farm
You likely already know how important maple syrup is to the Green Mountain State, but a visit to a working sugarhouse puts it in an entirely new perspective. Sugaring season is in the spring, but Sugarbush Farm converts their sugar house into an educational display during the off months, with an educational video and exhibits that illuminate how maple syrup is made. There are also farm animals, nature trails, a country store, and plenty of space on this 500 acre farm to enjoy the fantastic fall foliage. Open until 5pm each day, be sure to make it out to this Woodstock gem.
Photograph Woodstock Covered Bridges
One of the most charming aspects of visiting New England is stumbling upon covered bridges. There are four covered bridges in the Woodstock area that you should be on the lookout for, with Middle Covered Bridge being the most popular due to its location right off the village green. Bright red Taftsville Covered Bridge is another very popular Woodstock covered bridge, and it is one of the oldest covered bridges in the US. Lincoln Covered Bridge and Queechee covered bridge are the other two most popular bridges in the Woodstock area, and truth be told every single one on this list is photogenic with a ton of classic Vermont charm — especially when the fall foliage colors around them offer the perfect backdrop.
Indulge in Dinner at Cloudland Farm
Dinner is served at Cloudland Farm Thursday through Saturday by reservation only, so this isn’t a last minute dinner kind of place. However if you’ve been able to snag a spot here, you’ll be in for a treat! Located just outside of Woodstock in darling Pomfret, the drive to get to Cloudland Farm is absolutely gorgeous in the fall. The farm itself is the epitome of pastoral beauty, and the views from the veranda as you wait to be sat for dinner service are breathtaking. This is a bit of a fine dining experience, and it is a fixed 3 course menu that is expertly prepared by Cloudland’s chef.
Go Hiking at Marsh-Billings-Rockefeller Historical Park
When it comes to fall activities in Woodstock and throughout the state, hiking is always at the top of the list. The Marsh-Billings-Rockefeller Historical Park is home to over 20 miles of trails that wind their way through and around this beautiful protected space in Vermont. The forests are made up of
a variety of trees that create the symphony of fall colors, including Sugar Maples, the tree most commonly responsible for that brilliant scarlet red you’ll find dotting the Vermont landscape in fall. The Pogue at Marsh-Billing-Rockefeller National Historical Park is an especially scenic place to walk on a fall afternoon, as the fall foliage surrounding this pretty pond makes for quite the picture in the autumn months. You can also access the South Peak on Mount Tom at this historical park, offering access to one of the best aerial views of Woodstock. Plus, one of the access roads for this particular hike is a part of an intricate historic carriage road system that was created back in the 1800s, so it’s an interesting area to explore.
Enjoy Queechee Gorge Village
Two quintessentially Vermont things can be found at the Queechee Gorge Village: cheese and antiques! With 17000 sq feet, the Vermont Antique Mall is one of the best in the US and is a definite must visit for any lover of collectibles, memorabilia, antiques, and more. Treasure hunting in this epic antique store is a great rainy day Woodstock activity. You can sample Cabot Cheese, feed alpacas, and pick up all kinds of Vermont souvenirs at this outdoor shopping center. Don’t forget to stop by the Queechee Gorge Bridge to take in those awesome views with the fall colors are ablaze.
Billings Farm and Museum
Billings Farm and Museum isn’t just a fully functioning working farm, it’s an outdoor history museum, too! This iconic Woodstock spot is open daily through October, then weekends only for the rest of the season, but there is an absolute plethora of fall activities to be found onsite, including touring the museum exhibits, visiting the farm animals, and strolling through the gardens (Oh, and the ice cream shop is open through October, too!). They host a variety of events throughout the year, including their annual Harvest Celebration, Family Halloween event, and Thanksgiving Weekend throughout the fall season.
Where to Stay During Fall in Woodstock, Vermont
The Woodstock Inn
The Woodstock Inn has been a fixture in Vermont since 1793, starting out as The Richardson Tavern (which continues to serve as one of the Inn’s two restaurants serving up steaks and a to-die-for fondue). In 1830 it was expanded to become the Eagle Hotel, and today you’ll find eagles of all shapes and sizes throughout the property as a nod to it’s historic past. The original Woodstock Inn was built in 1892 becoming Vermont’s first winter sports destination. In 1967 the property was bought and renovated by Laurance Rockefeller (yes, of that Rockefeller family) and most recently a $16 million dollar renovation was completed in 2018. Today the overall feel of the Woodstock Inn is that of your most stylish friend’s country home – if that home came with an effusively nice staff, two world class restaurants, a luxurious 10,000 sq. foot spa, and activities to suite every taste and season.
Fat Sheep Farm
If you’re looking for a unique place to stay during your fall weekend visit, you’re going to want to check out Fat Sheep Farm. This working farm is so cute, and the property is extremely picturesque. We stayed in a modern cabin that was very comfy, with spectacular views of the Vermont countryside and the mountains in the distance. Our cabin had beautiful natural light, and after dark, the starry sky was breathtaking as we took in the night air on our porch. We participated in some of the farm chores like collecting eggs from the chickens and leading the sheep and goats from the barn to pasture. You don’t have to participate, but we wanted to get the full experience. We even tried our hand at milking the sheep! Added bonus: if you stay at Fat Sheep Farm, you’ll be just up the road from Harpoon Brewery, where you can enjoy a Harpoon Craft Cider, the perfect way to celebrate fall flavors… yum!
506 on the River Inn
Looking for an inn with gorgeous fall foliage views in Woodstock? We loved our stay at 506 on the River Inn, in part due to its peaceful location on the Ottaquechee River. The fall foliage views alongside the river can be enjoyed from your private riverside balcony, or while enjoying the firepit. There are complimentary s’mores each night from 7-9pm!
Offering a boutique inn experience and generous amenities that include onsite dining, a heated indoor pool, sauna, and comfy cozy rustic yet modern Vermont vibes throughout. They also have an outdoor playground and indoor kids’ play rooms that are so nice to have if you’re traveling with the fam! We really appreciated the toddler play space. There are lots of fun fall things to do in Woodstock, Vermont. Hopefully this list of places to go and things to do will help you plan your fun fall trip to Woodstock!
If you like this post be sure to check out some of my other articles!
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The Best Fall Destinations in Europe
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Amy Hartle
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