Day 1: The Road Begins: Halloween, Headless Horsemen (adjacent), and “See you Laters”

Croton-on-Hudson, NY | October 31| 40°F, Windy and Rainy

It’s officially begun.

After weeks (okay, months) of planning, packing, prepping, finishing work transitions, and saying “see you later” to so many dear friends, family, and colleagues, we finally rolled out of the driveway and into our next chapter. It wasn’t easy pulling away but as we reminded everyone, this isn’t goodbye. It’s just see you later.

And because timing is everything, our launch day happened to fall on Halloween. Which, honestly, felt perfectly fitting. I dressed as Ms. Frizzle, Don as Bill Nye the Science Guy, and Lucky as our sweet Bat Dog. We climbed aboard our own version of the Magic School Bus and hit the road on a rainy, super windy Halloween afternoon. It was the kind of weather that makes you second-guess your life choices… and then laugh because it’s exactly how every great story starts.

Our first stop: Croton-on-Hudson, not far from Sleepy Hollow, home of the Headless Horseman himself. Between the stormy skies, and our costumed sendoff, it felt like we’d driven straight into a storybook. The temperature was a brisk 40°F when we left the Finger Lakes, warming to a modest 45°F here. Not exactly the 70° we’re chasing, but at least we’re heading in the right direction.

Speaking of the campground: we pulled in after 8 pm, rain letting up but the wind still howling and were greeted by the night guards at Croton Point Campground with warm smiles, a quick orientation, and all the info we needed to get started. It was a warm welcome, and exactly the kind of friendly touch that sets the tone for a journey like this.

As we settle into this first stop, I’m starting to think about what I want to track along the way, maybe a few practical things (like mileage, campground notes and gas expenditures), but also the less tangible: the people we meet, the unexpected kindnesses, the small discoveries that remind us why we took this leap.

We’ve committed to a year on the road, but we’re also giving ourselves permission to let it unfold naturally. No expectations, no rigid timeline, no fear of “not making it the full year.” Just curiosity, intention, and a healthy dose of humor for the moments that don’t go as planned.

It’s cold, yes. The bus creaks in the wind, and I’m still figuring out which cabinet the coffee mugs ended up in. But this is it:  Day 1 of a new life, a new rhythm, a new way of seeing the world.

Here’s to the road ahead, the warm weather we’ll find (eventually), the warm greetings found and to come, and the adventures that begin with a little rain, a headless horseman, and a very determined Bat Dog.

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