Autumn Adventure: 5 Days in Vermont

Full itinerary for an extra long weekend in central Vermont

Vermont gets a lot of hype on social media every fall—and for good reason.

I love this state. It’s perfect for nature lovers with endless hikes and skiing options. But it’s also good for less outdoorsy pursuits with quaint villages and shops dotting the landscape.

There’s a lot of history here and it’s an easy drive across New York State for me. I’ve been all over Vermont and have yet to find an area I don’t like.

So when my fiancé requested a “quintessential Vermont” getaway, I was thrilled. We stopped in the Stowe area on a previous trip, but otherwise, he hadn’t seen much of the state.

We chose central Vermont for this trip. The central location made it easy to get to everything we wanted to see and, outside of Woodstock, it’s a little less frequented this time of year.

I’m sharing our full itinerary with links to all of our favorite restaurants, shops, and sights. Enjoy this gorgeous state!

Perfect weather at Little Rock Pond Loop in Green Mountain National Forest.

Where to Stay

Ludlow, Vermont

Located at the bottom of Okemo ski resort, Ludlow was a great home base for our trip. It was less than an hour from almost everything on our list and had several restaurants and bars to choose from.

Best of all, we were able to find an Airbnb right in the middle of town for much cheaper than Woodstock or other areas.

What to Do

Day 1: Woodstock

We drove directly to Woodstock to spend the afternoon in this adorable locale. If you aren’t staying in town, you only need a few hours to walk around and shop. It’s so picturesque and exactly what you imagine a Vermont village to be.

Expect Woodstock to be extremely crowded come leaf season. Even on a Thursday, most restaurants were booked, so I highly recommend making a reservation as early as possible.

This was the only place on the trip where parking can get tricky. There’s metered parking on the main village streets (free on Sundays), but you can park for free on Elm Street and off Pleasant Street, west of the Town Hall, or at the elementary school (weekends only).

These were a few of our favorite stops: