A Mother-Daughter Fall Getaway to Woodstock, Vermont

Last Updated on March 20, 2026 by Adrienne

While we have four seasons here in the Midwest, nothing compares to fall in New England. I lived in Boston for seven years and every year when the leaves start to turn I dream about going back to that region. This year I made it happen with a long weekend trip to Woodstock, Vermont with my 4 year old. We traveled in mid October (Columbus Day weekend) and I think we lucked out and pretty much hit peak foliage.

What we did:

Exploring the village of Woodstock and environs.

While Woodstock doesn’t have a ton to “do” it’s a very picturesque little New England town. There’s a covered bridge just off the main downtown area, and lots of beautiful foliage in the town itself.

Woodstock goes all out decorating for fall and Halloween, and we admired all the cute window boxes and front porches.

On Wednesday nights, there’s a farmer’s market on the Village Green and the whole town seems to gather for it (in a scene that felt straight out of Gilmore Girls). We got amazing wood-fired pizza for dinner from a vendor there.

Woodstock is located on the Ottauquechee River, and a walk to/along the river is beautiful and manageable even with younger kids.

Billings Farm & Museum.

Billings Farm is just a short walk outside of Woodstock and admission was included with our stay at The Woodstock Inn (more on the Inn below). This is a great place to bring younger kids. The grounds are beautiful with lots of foliage and fall displays, and there are cows, sheep and horses to meet and pet.

Don’t miss the chocolate milk from their onsite cafe (made with milk from their cows). It was a huge hit with my kiddo, who declared that it tasted like ice cream.

Sugarbush Farm.

Sugarbush Farm was a big hit with my kid, largely because of the small playground and play area with trucks.

I was a fan of the bucolic setting and the fact that admission is free. The “Maple Walk,” a trail through the woods that takes you under golden maple trees, has lots of information about how the tapping process works in the spring.

There are a few animals here too, including a goat, but I would say Billings is the place to go for animal encounters. The foliage and the playground are the real stars here.

Quechee Gorge

This was a quick photo op – we pretty much just hopped out of the car, snapped a pic and hopped back in – but I’m glad we went. It’s not too far out of the way from Woodstock and is one of the prettiest vistas we saw in Vermont.

Scenic drives

One of my favorite things to do was just drive around, and we saw some of the best foliage from the road.

We stopped at the Taftsville Covered Bridge, which is a beautiful bridge with a waterfall right next to it.

And also visited peaceful Silver Lake.

Where we stayed: The Woodstock Inn & Resort.

The Woodstock Inn describes itself as “Vermont’s most beautiful address” – a bit arrogant perhaps, but they’re not wrong. The grounds of the hotel are absolutely beautiful, and the inside is lovely as well.

Woodstock is a beautiful place to visit in the fall, and I’m so glad I got to see it. What are your favorite destinations for leaf-peeping?

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