A Cozy Vermont Fall: Burlington, Stowe & Woodstock

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Kerrylynn Regan
Curated By

Kerrylynn Regan

  • Weekend Getaways

  • Nature Escapes

  • Active Travel

  • Road Trip Travel

  • Vermont

  • Fall

Advisor - A Cozy Vermont Fall: Burlington, Stowe & Woodstock
Curator’s statement

Vermont is especially magical in the fall, with its small-town charm that feels straight out of a Hallmark movie. As the temperatures drop, cozy bars and restaurants glow, serving amazing food that makes lingering inside just as appealing as being outdoors. Quiet hikes bursting with colorful foliage offer moments of peaceful escape.

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Where to stay in Vermont

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Things to do in Vermont

Woodstock Middle Bridge

  • Walk around Battery Park and Waterfront Park in Burlington, Vermont: A fall walk in Burlington is crisp and peaceful, with Lake Champlain stretching out under a cool autumn sky. Colorful leaves frame the path, with the Adirondacks glowing in the distance. Afterwards, treat yourself at Lake Champlain Chocolates Flagship Store, where the smell of rich chocolate pulls you right in.

  • Explore Stowe: Downtown Stowe feels quaint and postcard-worthy, with a stop at Stowe Mercantile and a classic photo op from the Stowe Community Church viewpoint. The iconic covered pedestrian bridge, Giles W. Dewey Memorial Bridge, ties it all together, framed by charming buildings and mountain views.

  • Hike Stowe Pinnacle and Hogback Mountain: This hike is peaceful and rewarding, with quiet trails covered in colorful leaves. We even had a light flurry of snow towards the end of our hike, which added to the ambience. The panoramic views from the top make the climb feel especially magical and serene.

  • Drive Smuggler’s Notch: This is an experience in itself, with winding roads through blazing foliage and plenty of pull-offs to stop, get out, and explore. Each pause reveals towering cliffs, crisp mountain air, and views that feel straight out of a postcard.

  • Watch the sunrise at Queechee Gorge: We watched the sunrise from the bridge, which felt especially calm and unforgettable. Afterwards, we hiked the forested trails leading down to the rushing water below.

  • Explore Woodstock: Downtown Woodstock is classic New England charm, with stops at F.H. Gillingham & Sons and Woody’s Mercantile lining the village streets. Nearby, Billings Farm & Museum adds a timeless feel with plenty of things to see and do.

  • Take a covered bridge tour: While driving through Vermont, be sure to stop at some of the many covered bridges in the state. It feels like stepping back in time, each one framed by rustic charm and surrounding nature. We stopped by Brookdale Bridge, Gold Brook Covered Bridge, Middle Covered Bridge, Taftsville Covered Bridge, Lincoln Covered Bridge, and Quechee Covered Bridge.

Places to eat & drink in Vermont

Morse Farm Maple Sugarworks

  • August First: This bakery was voted “Best Lunch” and is known for their award-winning pastries. My boyfriend tried their special, a Thanksgiving-themed sandwich, and deemed it “the best sandwich I’ve ever had.”

  • Foam Brewers: This is a lively lakeside brewery known for its craft beers, dog-friendly patio, live music, and laid-back vibe.

  • Idletyme: We loved this brewery! We sat outside by the firepit with hot cider while we waited for our table. The warm, inviting interior set the perfect scene for a comforting and delicious dinner.

  • Doc Ponds: We tried a few different dishes and every single one was amazing. Great food, great beer, and the kind of place that makes you want to linger a little longer.

  • The Bench: This is a great spot for a more relaxed meal. We ordered some wood-fired pizzas and watched football at the bar area.

  • von Trapp Brewing & Bierhall: Founded by the von Trapp family, this brewery feels like a little slice of the Alps right in Vermont. We enjoyed sampling the Austrian beers and lunch selections. We also really enjoyed exploring the grounds (and seeing the cows) of the von Trapp Family Lodge & Resort.

  • Morse Farm Maple Sugarworks: We stopped here on our drive from Stowe to Woodstock as we wanted to try an authentic maple creemee. It is a charming, family-run maple farm set in the stunning countryside. The creemee was well worth it and we had fun browsing the shop as well!

  • Richardson’s Tavern at Woodstock Inn & Resort: This is a must-try for its timeless tavern fare, warm and historic ambiance, and exceptional cocktails—perfect for savoring classic New England comfort food with a refined twist.

Need to know

I highly recommend renting a car so you can easily explore the different towns. We visited a week or two after peak foliage and loved it—there were still beautiful leaves, but without heavy traffic or crowds. While we enjoyed a romantic getaway, this trip would be perfect for anyone looking for a weekend filled with hiking, charming small towns, cozy fall vibes, and amazing food.

Kerrylynn Regan

Travel Advisor

Kerrylynn Regan

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For more inspiration and insider recommendations, visit our Vermont page.