The town of Sleepy Hollow and Tarrytown inhale and exhale the essence of Halloween. The New York small-town charm will transport you into a classic 2000s Halloween movie. I recently had the opportunity to explore these wonderful New England-style towns. While I was there, I couldn’t help but smile at the similarities between these towns and my name-sake show, “Gilmore Girls”. The fan-favorite garners special attention during the fall as its small-town setting enhances the season’s charm. If you start the first episode on the first day of fall, the TV show takes you on a journey through the seasons. You’ll follow the story of an extremely close mother-daughter pair and everything that life throws at them.
While driving into Sleepy Hollow, I was half expecting “There She Goes” by The La’s to start whimsically playing in the background. Pulling into the center of Tarrytown was like jumping onto the Warner Bros. set of Stars Hollow, Connecticut. Coffee shops, bookstores, small restaurants, vintage stores, and local fire departments with Halloween orange vehicles. The type of community and spirit that I thought was only seen through a screen. Lorelai and Rory Gilmore would absolutely fit in with the people of Sleepy Hollow and Tarrytown.
Another movie that came to mind as I spent time in these towns was the 1998 classic witch movie, “Practical Magic”. Starring Sandra Bullock and Nicole Kidman, “Practical Magic” is about family, love, luck, and, most importantly, witchcraft. You can almost hear Bullock’s voice echoing across the town, saying, “Always throw spilled salt over your left shoulder, keep rosemary by your garden gate, plant lavender for luck, and fall in love whenever you can.” I also highly recommend listening to the iconic movie soundtrack featuring songs, “If You Ever Did Believe” by Stevie Nicks and “A Case of You” by Joni Mitchell. These artists encompass mystical witch tones in most of their music, which is the perfect kind to listen to while driving off the highway and onto the backroads of New York.
One of my favorite spots in Sleepy Hollow was, get this, the cemetery! The cold fall air, leaves falling around your feet, and screaming children running through the cemetery as their fathers chase them. If you’re having trouble picturing the Sleepy Hollow cemetery, just picture the one from “Hocus Pocus” and add more winding hills and centuries-old trees. This spooky, off-putting, but exciting area will have you looking for the Sanderson Sisters and Billy Butchersen as you round the corners. If “Hocus Pocus” wasn’t filmed in Salem, Massachusetts, then I could see director Kenny Ortega choosing Sleepy Hollow.
Another Halloween film I could see through the lens of Sleepy Hollow and Tarrytown is the Disney Channel classic, “Halloween Town”. The 1998 movie features Debbie Reynolds as a fun-loving, mysterious grandmother who only visits her grandchildren on Halloween. When her granddaughter Marnie starts to question her grandma’s strange abilities, stories, and unusual walking purse, she decides to follow Grandma Aggie onto the bus. This magical flying bus leads Marnie to a world she never thought possible, a world where she fits in perfectly, Halloween Town. Now, Sleepy Hollow doesn’t have vampires, werewolves, or goblins, but it does have the headless horseman! Washington Irving’s “The Legend of Sleepy Hollow” depicts a ghostly character who rides a horse holding his pumpkin head. I’m sure we’ve all heard a version of this story at some point. The legends of the town are endless, just like the fictional movie world of Halloween Town.
Between the town’s comradery, spooky sounds, celestial air, and legends, Sleepy Hollow is the perfect Halloween town. If you want live out your “Gilmore Girls” fantasy, check out the Muddy Water Coffee & Café. Get yourself coffee, and then you can be on your way to the Sleepy Hollow Cemetery and visit some famous graves, keeping your eye out for the ghouls and goblins from “Hocus Pocus”. Whatever movie you choose to reminisce about, Halloween classics keep the season’s spark alive and well.
