Fall in Vermont

Fall in Vermont is a most magical season. The foliage becomes an attraction in itself, and the cooler temperatures bring a renewed energy to enjoying the outdoors. While most spring and summer activities are still available, especially biking, hiking, kayaking and fly fishing, there are certain things specific to fall not to be missed – keep reading!

Important: if you are in the early stages of planning your stay with us in the fall, please be aware that this is our busiest season: book your room and your restaurants early!

As always, feel free to call or email us for questions.

Favorite things to do

forest covered in red foliage

Pick Apples

Click here for a list of orchards less than an hour from Woodstock.

Take in the scenery and take photos

Follow our suggested foliage route and let your inspiration guide you!


Faulkner park right behind the B&B, leading to Marsh-Billings-Rockefeller National Historical Park and beautiful views of Woodstock from Mount Tom. Click here for a trail map.

A portion of the Appalachian trail, crossing route 12 just 3 miles from Woodstock.

Mount Peg, right on the other side of town.

Tip: order a picnic from the B&B the day before for a hassle-free day out!


Right across from our B&B, Woodstock Wheels will set you up with an e-bike; click here to book your rental.

You can also rent a bike from Woodstock Sports and bike around town, alongside the Ottauquechee river, and up the trails of Mount Peg and Mount Tom. Or, take a short drive to Vermont’s newest lift-serviced trail park, Suicide Six Bike Park   (a less than 10-minute drive) or to Killington’s mountain biking park.  (about 30 minutes away). Electric bikes (e-bikes) are also available for rent from Hanover Adventure Tours and Vermont Bike and Brew (with drop off at and pick up from our B&B, as needed). 

Ready to bring it up a notch? Book a guided bike tour with Discovery Bike Tours. 

Also, check the following bike trails near Woodstock: Aqueduct Trails, Mt Peg Trails and Suicide 6 Trails.

Early fall: kayak and canoe, SUPs 

Silver Lake Park in Barnard offers rentals of rowboats, canoes, kayaks, pedal boat and SUP 

Wilderness Trails and the Vermont Flyfishing School offers several options, from a leisurely paddle on the Connecticut River to a more adventurous kayak trip on the White River, to canoe and kayaking in a wildlife sanctuary.

Great River Outfitters in Windsor offers float trips, canoes, kayaks, SUPs, rafts and river tubes on a section of the Connecticut River.

Early fall: fly fishing

Wilderness Trails and the Vermont Flyfishing School will pick you up at the B&B bright and early to catch some Vermont trout and spend an unforgettable day in pristine nature. Ask us to book your fly fishing excursion or contact Pete directly. Definitely put this on your list of things to do in Woodstock, VT if you love nature and the outdoors!



Fall main event: Apple and Crafts Fair in October.

The Market on the Green and Feast & Field continue throughout mid-October.

Check out the places to visit in Woodstock, the restaurants (book your fall dinners early), and the shops!

Fall was last modified: July 3rd, 2024 by Isabelle Chicoine