A Three-Day Itinerary to the Best of Fall in Vermont

For a long-weekend getaway from New York City this fall, we rented a car and drove north to catch some of the best leaf-peeping on the east coast. In early and mid-October, Vermont is the autumn version of a winter wonderland: foliage so bright you can’t really capture it in photos, perfectly crisp weather, picturesque towns set into the rolling mountains.

The further north you drive, the more the scenery starts to look like Switzerland or Austria – so it’s little wonder that this is where the von Trapp family chose to settle after the nuns helped them escape Salzburg*.

We spent most of our drive along Route 100, but the landscape and fall colors are so fantastic that even the freeway has some postcard-worthy views. Here’s my plan for a perfect three-day getaway from the city.

*Okay, okay, that’s not exactly how it happened.

Day 1

Warren and Stowe

Grab your suitcase and coffee and start driving north. Might I recommend this fall playlist? Once you cross into Vermont, plan for plenty of stops along the way – picture-perfect views, apple donuts, and maple creemees (a local maple syrup softserve) are all worthy detours. The Weston Vermont Country Store and Amherst Lake were two of my favorite spontaneous stops.

Plan a lunch break in the tiny town of Warren. Get a sandwich from the general store, but don’t leave without browsing around and grabbing a jar of this spicy mustard (my favorite discovery of the trip). Find a table outside or a spot next to the waterfall to eat lunch, then stroll around town before getting back on the road.

Follow Route 100 all the way up to Stowe, Vermont. We settled in at Edson Hill, where we had dinner in the Dining Room restaurant. If you’re there, ask for a corner bench table or a spot next to the fireplace for ultimate coziness. And don’t miss the fire pit on the patio!

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Day 2

Smuggler’s Notch, Cider Slushies, and Queechee

I know it’s the weekend and a vacation, but I promise that (1) this is worth the wakeup call, and (2) you can sleep in tomorrow. Before breakfast, pull on a hat and a sweater and make the short drive up to Smuggler’s Notch.

Give yourself about an hour to enjoy the scenery before all the other travelers, hikers, and their many cars start to clutter the zig-zagging road. Afterwards, take your time warming up over a long breakfast back at the hotel.

Head back out and make your way up to the mountaintop Trapp Family Lodge. The classic Austrian-style lodge has wonderful views and gardens – we spotted more than one family photo session happening here. When you’re ready for lunch, drive down into Stowe and stop in at the general store.

Next, take the scenic route to Burtt’s Apple Orchard. The same road trip rules apply as yesterday: brake for maple creemees, wonderful views, any roadside maple syrup stands. The orchard has pumpkins and apples of course, but what you’re really here for are the exceptionally good apple donuts and the apple cider slushies. Buy more donuts than you think you need, and strongly consider never drinking hot cider again.

After you’ve walked through the orchard and solved the corn maze, it’s time for the last stop of the day: Queechee. Plan to arrive before sunset to see the falls and the covered bridge that spans the river before your dinner reservation at Simon Pearce. If you find yourself sans reservation, put your name on the list for a table in the Bar and explore the glasswork studio while you wait. Either way, the Vermont cheddar soup is a perfect way to end the day.

Note: To save yourself some driving, you could spend the night in Queechee or nearby Woodstock. However, during the peak fall season, many hotels have a two-night minimum stay.

Day 3

Woodstock and Leaf-Peeping

Give yourself a slow morning today; sleep in and head down to breakfast, then come back to pack up your things and check out of your room.

Back on the road again, drive towards Woodstock, Vermont. This pretty town feels like the real-life version of Stars Hollow – all it’s missing is a gazebo! You can park just about anywhere, then wander through the town square and side streets to spot photo-worthy fall decorations and cute shops to explore. Make sure to see the covered bridge and the famously chic Woodstock Inn. Have a leisurely lunch at the Inn or stop at the general store and make a picnic out of it.

By now you’re an experienced leaf-peeper, and you know that the best part of this road trip is simply driving through the autumn wonderland and taking it all in, stopping whenever you like. On the drive back south to the city, I must insist that you stop for a maple creemee if you haven’t had one yet. When the sun has set and you’ve still got an hour or two to go, remember your extra donuts from Burtt’s and thank your past self for being so thoughtful.