A Halloween Roadtrip to Sleepy Hollow, NY

October belongs to my husband. Lover of all things spooky, fall-related and Halloween-adjacent, Mike spends October watching his extensive horror movie collection, consuming all things pumpkin and exclaiming over foliage. For his 30th birthday, I surprised him with a Halloween adventure to the spooky little town of Sleepy Hollow, New York, someplace that had been on his wishlist for awhile. If you’re looking to take a Halloween roadtrip, this is the post for you.

Located about 8 hours from Toronto, Sleepy Hollow is a village in New York state. It’s only an hour outside of Manhattan. Best known as the village from The Legend of Sleepy Hollow by Washington Irving, they’ve fully committed to Halloween in the month of October. Your own Headless Horseman sighting awaits…

A Halloween Weekend in Sleepy Hollow

Halloween in Sleepy Hollow, NY is exactly what you’d expect. Historic Hudson Valley puts on a number of events that highlight the town’s history, lean into the Legend of Sleepy Hollow and embrace the season. The quaint village has orange and black street signs, pumpkins abound and a spooky spirit that hangs in the air.

Irving’s Legend (Old Dutch Church)

You can’t visit Sleepy Hollow without hearing its namesake Legend performed live. Irving’s Legend is performed in the Old Dutch Church, an intimate and historic setting. Legend is one of the only ways to visit the beautiful church. This one-man show The Legend of Sleepy Hollow is key to understanding the appeal of the town. Attending Irving’s Legend in The Old Dutch Church lets you hear this legend firsthand while sitting in a beautiful church at the centre of the legend. Jonathan Kruk, The actor who delivers the legend, is fully committed to his character, pacing the aisles of the church and immersing you in the tale. A year later, we’re still talking about our trip to Sleeeeeepy Hollowwwww. The show is completely family-friendly, but the little girl in front of us did jump a few times.

Buy tickets to Irving’s Legend

Visit the Sleepy Hollow Cemetery

The Sleepy Hollow Cemetery was one of the highlights of the trip for us. For starters, it’s incredibly beautiful. If you’re looking for fall foliage, you’ll definitely get that in the cemetery. It’s also a wonderful walk along a paved, hilly path. I recommend visiting both during the day and at night for the Lantern Tour of Sleepy Hollow Cemetery.

The Lantern Tour is exactly what it sounds like: wandering through the Sleepy Hollow Cemetery at night, in the pitch black, lit only by oil lanterns. We did this on our first night and it was the perfect way to kick off our Halloween adventure. The tour takes you through the many twists and turns of the cemetery, highlighting some of its most interesting inhabitants and sharing their stories. We saw the graves of Washington Irving (author of the Legend of Sleepy Hollow), members of the Rockefeller family and Andrew Carnegie, among others.

We also ventured inside the cemetery’s “holding area” for bodies that arrived during the winter months. Before modern digging technology, the bodies would rest in this temporary home until the ground thawed. For me, this was the spookiest part of our tour.

Buy tickets for the Sleepy Hollow Cemetery Evening Lantern Tour

The Great Jack O’Lantern Blaze

We experienced this attraction in the pouring rain and still left in awe. Thousands of pumpkins ablaze is definitely a sight to be seen. As you walk a winding path, you’ll come across dozens of pumpkin installations.

The Blaze is outside of Sleepy Hollow – you’ll want to drive there – and conveniently not too far from a Shake Shack if you’re looking for a pre-Blaze meal. They’re very serious about the timed entry, so try to leave just enough time to park, get a warm beverage and hop into line. The upside of this is that the attraction is not extremely crowded and you can go your own pace as you meander through the path.

Buy tickets for The Great Jack O’Lantern Blaze

Dinner at Bistro 12

After a disastrous dinner on the Friday night of our trip (think $25 tomato salad with a single tomato and a super-fatty steak), we stumbled upon Bistro 12.

Located on the main strip in Tarrytown, Bistro 12 is a Mediterranean restaurant with Portuguese fare. We had a languid meal filled with delicious wine, each bite more delicious than the next. I enjoyed a short rib that I still think about. When we declined dessert, they brought out a house specialty. It was exactly the kind of ambience, service and food you want in a new city.

Tips for Visiting Sleepy Hollow

  • Bring a vehicle. We were always grateful to have our car, although it is possible to take the train into Tarrytown / Sleepy Hollow from New York City. Activities like the Pumpkin Blaze take place outside of town and the weather is a bit finicky in October.
  • Plan day trips or stay outside of Sleepy Hollow. Sleepy Hollow is a bit…sleepy. Outside of the various activities we had planned, there wasn’t much to do. It makes for a perfect, jam-packed day trip. If you do stay in town, consider…
    • A day trip to New York City – an easy drive. Parking in the city is very expensive (think $60) but once you’re there, it’s easy to get around. We met our cousin Vinny for lunch at the storied Keens Steakhouse.
    • Target in White Plains – no explanation needed
    • Antiquing in Hudson Valley – lots of picturesque small towns are a short drive away
    • Woodbury Commons – the famed high-end outlet mall with brands like Prada, Burberry and Saint Laurent.
  • Book early! Prime time slots book up quickly, so if you want to experience multiple activities you will want to get organized early on. This also goes for lodging – we booked one of the last rooms at the DoubleTree by Hilton Tarrytown, a clean and comfortable hotel with super-friendly staff just off the highway in neighbouring Tarrytown.
  • Bring warm (and waterproof) clothing. Have I mentioned the weather? It was very October-ish, so boots, a water-resistant coat and scarves, mitts and a hat were key.

I hope our experiences in Sleepy Hollow during the October Halloween season have helped you plan your own spooky adventure! Our next Halloween trip will probably be to Salem, MA – let me know in the comments if you’ve ever visited.