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Cover Bridge in Woodstock, VT

From The Blog The perfect weekend in Woodstock: Fall edition

Autumn leaves & pumpkins, please!

When there's a snap in the air and the trees erupt with eye-popping shades you can feel autumn everywhere. It's in the food, the cozy fire-lit rooms, the chunky sweaters, it's even in the rosy glow of your cheeks!

And although it's impossible to capture that magic without living it firsthand, we're compiled this itinerary so you can envision yourself in our autumnal wonderland...

October fall river view
Woodstock Inn pumpkins fall
A parade of pumpkins at the Woodstock Inn


While you're packing the car, hitting the road, and crossing over the Vermont border, local B&Bs, resorts, inns, and motels are ready to welcome you.

Village Living

If you’d like your pumpkin spice latte source to be right outside your door, then a stay within the village is for you! Every kind of accommodation, from the grand Woodstock Inn & Resort to the river views of The Shire is at your fingertips.

B&Bs such as the Woodstocker, the Vesper, and the Village Inn offer convenience and history all wrapped into a charming package. But don’t delay – fall foliage is one of the busiest seasons in Woodstock and rooms fill up fast!

Foliage in Woodstock Vermont

In the Country

If immersing yourself in the vibrant shades of nature is your aim, there are plenty of options for staying just outside of town:

Day 1

First thing’s first! Strap on your walking boots, hop out of the car, and stretch your legs with a brisk walk through Woodstock’s village – infused with an extra dose of charm thanks to the vibrant colors of fall foliage.

Insider tip: If you're eager to extend your trek, you're in luck! There's a river walk in Woodstock, and it begins right inside the village. 

Town of Woodstock

Be sure to hit Central and Elm Streets for a smorgasbord of family-owned shops, from Woody's Mercantile, Vermont Eclectic Co, and village art gallery, Focus, to beloved mainstays like the Vermont Flannel Co (tis the season for comfy and cozy fleece-wear) and of course the Collective, an artist owned and cooperatively run gallery.

Warm up for a moment or twenty at Clover Gift Shop, an apothecary and home-goods extravaganza, and get lost in the whimsical wonderland of Unicorn Gift Shop, while N.T. Ferro Jewelers beckons to those seeking something that sparkles. But wait, there's more!

Looking for a quick bite? You’ll find that too – at spots like Soulfully Good Café, and the Village Butcher.

Wagon rides at Billings Farm during fall foliage
Judy Laliberte
Billings Farm offers plenty of photo-worthy perspectives

If you’re joining us in September or October, head up Elm Street by foot or by car to spend some quality time at Billings Farm & Museum (great for the kids thanks to a stunning sunflower house (open through mid-September), pumpkin bowling, and storytelling) and Marsh-Billings-Rockefeller National Historical Park for a one-two punch of culture and exercise. Both locations offer breathtaking views of the changing leaves for those avid leaf peepers among us – and if you’d like a bird’s-eye view of the village, head to the top of Mt Tom via a moderate 4.2 mile round-trip loop passing rolling hillsides and the Pogue, a stunning 14-acre mountain pond.

After that, you’ve earned a scrumptious dinner on the town. Nosh inside or out on the patio at your choice of the historic Prince & the Pauper restaurant or Dr Coburn's Tonic. You can also up the cozy factor by dining fireside at Richardson’s Tavern in the Woodstock Inn!

Craving a meal in the countryside? Get the farm-to-table experience at Cloudland Farm just outside of town– or take in the views of Kelly Way Gardens while sampling its bounty of fresh, delicious produce as part of the Red Barn Dinner Series! Reservations required.

Day 2

The leaves are falling – there’s no time to waste! Rise and shine with a little help from a butterbeer latte and pumpkin pancakes (seasonal items, of course) at Mon Vert Café or the ever-classic Mt Tom at Mountain Creamery (now in its new location), offering a plateful of eggs, meat (we recommend the homemade corned beef hash), and pancakes.

Then, find the activity that’s just your speed: whether it’s mountain biking at Saskadena Six, the Aqueduct Trails, or Mt Peg, exploring the glorious shades of fall atop your trusty steed, or taking a family tour to the treetops via the Forest Canopy Walk at VINS, perfect for up-close-and-personal leaf-peeping! 

Fall foliage in Vermont, Vermont Farm
Sugarbush Farm
Fall view of Sugarbush Maple & Cheese Farm

In the mood for food? For a fancy take on lunchtime, delve into the Woodstock Inn & Resort for the Red Rooster’s flavorful offerings, from lunch plates to seafood stew. Or if you’re looking for a quick and tasty slice, stop by Pizza Chef just outside of the village.

Hear that? Sugarbush Farm is calling – with its stunning vistas, a cavalcade of adorable farm animals, a sugar house open for self-tours, an Instagram-worthy chapel in the woods, and delicious cheeses and maple syrup made directly on the premises. Plus, the scenic drive there makes this one a no-brainer.

After that, nip into your accommodations if you’ve got a moment to spare before heading out for supper. For a meal that’s locavore cool, visit Santé or Worthy Kitchen, its kids-friendly counterpart. For flavorful fare with more exotic roots, check out Angkor Wat or Melaza Bistro. And if you’re looking for Neapolitan-style pizza with all the style of a Brooklyn gem, do not miss out on The Ransom Tavern (hello, bar scene)!

Day 3

Autumnal fun awaits on your final day in Woodstock. Make the most of this travel day by grabbing breakfast to go at the delightful South Woodstock Country Store then heading toward u-pick paradise. September through mid-October, apple picking is your go-to game at Moore’s Orchard (at the intersection of Pomfret Road and Johnson Road in Pomfret) and Whitman Brook Orchard on Wheelock Road in Taftsville – with over 100 (yes, you read that right) varieties of apples to pick from... pun intended!

Apple on the tree in fall

When pumpkin picking season takes over, you can find gourds, squash, and your Jack-O-lanterns to-be on select dates at Fox Crossing/Ridgeline Farms on Webster Hill Road in Pomfret. Follow the country road for a taste of October in Vermont: Ox cart rides, hot and cold cider, baked goodies, and of course, fields filled with porch-perfect pumpkins! After you’ve filled your stomach with treats and your trunk with pumpkins, it’s time to hit the road. Snap and few pictures, and wave goodbye to one of Vermont’s most dazzling seasons.