This town near Ontario is a fall oasis with New England charm and whimsical covered bridges

It's known as "America's Prettiest Town."

A covered bridge during the fall. Right: A person holding a pumpkin on a street.

A covered bridge in a small town. Right: A street in a small town.

Lead Writer, Travel

Fall is one of the most beautiful seasons, with its stunning colours, crisp air and cozy vibes. It's an especially beautiful time of year in this small town which transforms into something worthy of an autumn fairytale.

Woodstock, Vermont is a breathtaking destination to visit during the fall. The historic village is located near Ontario and is a 5 hour road trip from Ottawa.

Dubbed "America's Prettiest Town," Woodstock is nestled within the Green Mountains of Windsor County and is brimming with colonial architecture, cozy shops and gorgeous views.

During the fall, the town turns into an enchanting autumn paradise with leaf-filled streets, breathtaking hikes and harvest adventures.

Some of the fall highlights of Woodstock include local farms such as Billings Farm & Museum where you can celebrate the harvest season and even enjoy a horse-drawn carriage ride through the fall colours.

You can also lace up your boots and hike through some gorgeous foliage. The Mount Peg Trail System offers twisting pathways through golden trees and panoramic lookouts, while Mt. Tom features stunning views of the village steeped in colour.

You'll want to spend some time exploring the quaint village. There are many local shops with unique goods as well as cafes and farm-to-table restaurants.

Woodstock is home to four enchanting covered bridges that are even more beautiful during the fall. You can soak up some New England charm as you explore the historic landmarks.

If you're looking for an overnight stay, you can book a room at one of the quaint inns, such as the Woodstock Inn & Resort.

Grab your passport and take a fall road trip to this enchanting autumn village.

Woodstock Website

  • Lead Writer

    Madeline Forsyth is a Toronto-based Lead Writer for Narcity Media. After earning her B.A. (Hons) at Queen's University, she spent a year travelling much of the world as a flight attendant. Now, she uses her experience in the travel industry and passion for writing to share stories about buzzworthy events and adventures across Canada and the globe. Madeline has been published in PopSugar and has interviewed sports and entertainment personalities for Narcity. She has covered and photographed restaurant openings as well as event launches such as the world premiere of the Dr. Seuss Experience. Some of her favourite things to write about include charming small towns and anything to do with Harry Potter.

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