The Best Things to do in Woodstock, VT This Fall

Jackson House Inn, Woodstock Vermont

Is there anything more spectacular than Vermont in the fall? We don’t think so, especially when you stay in a charming and breathtakingly beautiful town like Woodstock, VT! There are, of course, plenty of wonderful things to do in Woodstock, VT in the fall. However, one of the best reasons to make this your fall getaway destination is the chance to relax and unwind at the stunning Jackson House Inn.

The Jackson Inn is an exquisite boutique hotel just one mile from downtown Woodstock. We’re nestled in the quiet countryside just on the edge of town. We offer an unparalleled destination where couples love to retreat, unwind, and share some quiet, uninterrupted time. Between a stay here and time spent in what’s considered Vermont’s most beautiful village, you have the recipe for an unforgettable getaway this fall.

Whether you enjoy hiking, biking, shopping, or driving through beautiful countryside, you’ll find there are more than enough things to do in Woodstock, VT this fall. Make sure to give yourself plenty of time to soak up the experience at our elegant Vermont Bed and Breakfast – a place where you’ll feel your stress melt away from the moment you arrive. Book your room at our boutique hotel in Vermont today!

A beautiful covered bridge with fall foliage - one of the best things to do in Woodstock VT in the fall

Things to do in Woodstock, VT This Fall

There are so many incredible things to do in Woodstock, VT, especially in the fall, that it can be hard to choose where to start. That’s where we come in! Woodstock, VT oozes that small-town Vermont charm you crave this fall. With year-round recreation and entertainment, stunning natural beauty, and plenty of great food and drinks, Woodstock, VT, leaves little to be desired.

Fall is a beautiful yet busy time in Vermont – especially in a town as beautiful and popular as Woodstock. To help you navigate the town and make the most of your time here, we’ve compiled a list of ten of our favorite things to do in Woodstock, VT, in the fall season.

  1. Get up close and personal with some of Vermont’s most stunning fall foliage, and take a hike. A great place to do this locally is the Marsh-Billings-Rockefeller National Historic Park, the only National Park in Vermont. Our favorite hike here is the Pogue/Mt. Tom loop, which is 4.2 miles long. When you’re done exploring the park, head to the Billings Farm and Museum, co-located on the same property. It’s rated as one of the top-rated things to do in Woodstock each fall, and it’s easy to see why. The museum is regarded as one of the best outdoor history museums in the country, with plenty of gorgeous fall scenery to enjoy.
  2. One of our favorite things to do in Woodstock, VT in the fall is to head to the stunning Quechee Gorge. Once there, you’ll enjoy the beauty of Vermont’s deepest gorge surrounded by Autumn’s fiery, vibrant hues. This is one of the best places to admire the beauty of Vermont in the fall.
  3. Scenic drives are among the more popular things to do in Woodstock, VT in the fall. One of our favorite places to take a drive is Vermont’s newest scenic byway, The Crossroad of Vermont, which follows US Route 4.
  4. Enjoy a delicious taste of Vermont at the year-round Woodstock Farmers Market, where you can sample a variety of farm-fresh seasonal produce and delicious locally made products like fresh Vermont cheese. It’s a great place to pick up picnic supplies for a fall afternoon picnic!
  5. Enjoying great food is one of the top things to do in Woodstock, VT, but so is enjoying a great craft beverage at local breweries and distilleries. Favorites include Long Trail Brewing in Bridgewater and Caledonia Spirits in Montpelier – but you can also unwind with a delicious selection of wine, beer, and spirits available at the Jackson House Inn!
  6. Get to know local makers and artisans at the shops, galleries, and maker spaces around town. One of our favorite places is the Simon Pearce flagship store, but we also recommend Shackleton Thomas and Farmhouse Pottery.
  7. Seeing the historic beauty of Vermont covered bridges in the fall is one of our favorite things to do in Woodstock, VT – and there’s no shortage of great bridges to see! There are at least ten in the area, including the Blow Me Down Covered Bridge, Dingleton Hill Bridge, Downers Covered Bridge, Lincoln Covered Bridge, Martins Mill Covered Bridge, Middle Covered Bridge, Quechee Bridge, Taftsville Covered Bridge, Willard Covered Bridge, Windsor-Cornish Covered Bridge.
  8. Biking is a great way to get around Woodstock in the fall – including getting from one covered bridge to the next! Rent a bike locally, and we’d be happy to suggest a few scenic routes for you.
  9. Take in Vermont’s fall foliage from an entirely different vantage point on the treetop walk at the Vermont Institute of Natural Science in Quechee. You’ll walk 65 feet above the Ottauquechee River, making it one of the most exciting things to do in Woodstock, VT, in the fall.

Exterior Dusk 2

The Best Place to Stay in Woodstock, VT

You’ll need several days to truly enjoy this great list of things to do in Woodstock, VT. When it comes to finding a relaxing, beautiful, and upscale place to stay in Woodstock, VT, nothing beats the exquisite Jackson House Inn. Our Vermont Bed and Breakfast is situated on three gorgeous and well-landscaped acres and offers your choice of eleven luxurious guest rooms. All our accommodations are designed with your comfort in mind and feature a thoughtful array of high-end amenities to complement your stay.

Though everything at our Vermont Bed and Breakfast is extraordinary, breakfast is truly exceptional. We have two classically trained chefs at the Inn who do an excellent job of curating a delicious food-focused experience each morning. Using fresh, local, and organic products whenever possible, they serve a range of unique and sensational breakfast dishes that will leave you full, satisfied, and ready for a day of adventure.

As you can see, a getaway to Woodstock, VT, this fall will be both gorgeous and relaxing. Before you know it, the cozy winter season will be here, just in time for romantic getaways and special celebrations. If you haven’t already, make sure to book a room at our luxurious Vermont Bed and Breakfast today!

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