1. Stockbridge, MA: The Incredible Naumkeag Pumpkin Show


If you were to attend a pumpkin circus at a serene historic estate, you’d be at the Incredible Naumkeag Pumpkin Show. This gourd-geous event is one part serene, garden stroll through the Gilded Ages and one part pumpkin explosion. Last year, we wobbled through a blacklit “vortex” into a supernatural greenhouse, complete with Audrey II from Little Shop of Horrors (as a pumpkin, of course). Hot cocoa in hand, weave through paths of pumpkins carved as your favorite characters—the candlelit casts of Sesame Street and Golden Girls are on deck. Muster your courage to see the architectural glory of Naumkeag in the dark, alight with the glow of a giant, bubbling cauldron outside.
Date: Wednesdays–Sundays from October 1–31
Time Out tip: Getting there is just as fun! Park at one of the three zones and take a spooky, sparkling school bus up the hill to the estate. Costumes encouraged!