October

It starts with a crunch underfoot — leaves, crisp and curled, scattered across winding trails and quiet roads. Vermont in October doesn’t shout; it whispers in golden light and flickers of red in the trees, slowly wrapping you in its charm. The air smells like woodsmoke and apple cider, and every hill you crest feels like it's showing off — bursts of fiery red, golden yellows, and those moody dark evergreens peeking through. You drive down a winding road and suddenly there's a covered bridge straight out of a calendar, and you're like, "okay, Vermont, I get it... you're adorable." Farm stands pop up with piles of pumpkins, local maple syrup in glass bottles, and those awkwardly shaped gourds nobody knows what to do with but we buy them anyway. The small towns feel like cozy little secrets, with general stores that still sell penny candy and sweaters that smell like they were knit next to a fireplace. It's the kind of place that makes you want to slow down, breathe in the crisp autumn air.

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Why Grafton?

We chose Grafton, Vermont for October because, honestly—how could we not choose Vermont in the fall? It was actually the very first spot we picked when planning our adventure. We wanted a mix of big cities and tiny towns, and Grafton checked the “storybook autumn” box hard. It’s close to Halloween-y gems like Woodstock, Salem, and Sleepy Hollow, and just so happens to be near Jake’s brother’s wedding, too. Basically, it had all the magic we wanted in a fall chapter—colorful, quiet, and classically Vermont.

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Where Are We Staying?

Tucked into the folds of southern Vermont’s rolling hills, Grafton feels like a town time forgot—in the best way possible. With its white clapboard houses, winding country roads, and a general store that’s been around since the 1800s, it’s the kind of place where you half-expect to see a horse-drawn carriage pulling up for maple syrup. Grafton is small—really small—but that’s part of its charm. You don’t come here for hustle or hotspots; you come for slow mornings with coffee on a cabin porch, golden leaves drifting past the window, and evenings spent wandering past stone walls and covered bridges. It’s the perfect place to unplug, breathe in that crisp October air, and let the world feel simple again, even just for a little while.

This cozy country home offers a tranquil retreat surrounded by nature's beauty. Honestly, this place is adorable, it was also built by the owner's father so it is very Halle's family coded not to mention how much it resembles Jake's mother's famous schoolhouse. Also, have you seen the spiral staircase and old school stove? With picturesque views and a location that provides easy access to cute towns and nature, this Airbnb is an ideal spot for relaxation and exploration .