Westchester punches above its weight at the table. You can eat with the Hudson out the window one night and end up down a wooded back road the next, chasing a place someone swore you had to try. This is the running list of where we keep going back, split between the riverfront towns and the quieter spots inland.

Come October, this stretch of the Hudson leans all the way into the legend. The Headless Horseman is everywhere, and the whole village gets that crisp, slightly haunted feeling Washington Irving was writing about. Our favorites: champagne among the graves at the old cemetery, and a hayride that drops you deep in the dark woods.