Sleepy Hollow Road Trip

A trek to find the man, the myth, the legend - The Headless Horseman

In 2025, we checked off a Halloween bucket list item and travelled to Sleepy Hollow, NY, birthplace of Washington Irving’s The Legend of Sleepy Hollow. We’re pretty big fans of the early American tale, so much so we named our cats after characters. We convinced a few friends to venture into the land of legends and ghost stories in search of the Headless Horseman then set off on the 8 hour drive the weekend before Halloween. Below you’ll find the general itinerary for our trip. Nothing here is a paid promotion, just our take on a good old fashioned road trip into the Hudson Valley. It was the kind of Halloween fun my heart was missing - crisp air, stunning leaves, creative costumes, markets with handmade goods, deep lore, and friends to share the late night memories with for years to come.

Friday

1: Fuel up with pumpkin lattes at our local spot after packing The Pumpkin Car.

2: Drive 8 hours (plus a few extra with rush hour traffic). Entertainment: Bingo cards (download them at the bottom of the page); a 24 hour long Halloween playlist (find a small selection of the songs included over on the playlists page). Creature comforts: a snack basket with apple cider, candy corn, caramel apple candies, and caramel corn; black cat socks; fuzzy fall cat blanket.

3: Pull into town 15 minutes before the Sleepy Hollow Cemetery Evening Tour. Yes, they gave us real oil lanterns. Yes, we saw the burial site of Washington Irving.

Saturday

1: Lyndhurst Mansion Gothic Market (added the tin type photo as our souvenir from the trip)

2:Tarrytown Halloween Parade to feel like a kid again and cry with excitement over the Headless Horseman blazing through town. I lived in the moment so hard that I didn’t take any blog worthy photos.

3: Twilight Village at Philipsburg Manor for even more Headless Horseman encounters and fireside s’mores.

Sunday

1: Old Dutch Church and some daytime cemetery sleuthing to see Katrina Van Tassel. I have a cat named after her, and she was not just a storybook character.

2: Washington Irving’s Sunnyside to see where a Romantic wrote overlooking the Hudson. Bonus points for learning to walk on stilts on the lawn.

3: Great Pumpkin Blaze for pumpkins, pumpkins, and more pumpkins.