Discover Sleepy Hollow, New York: Spooky Season, Scenic Hikes & Great Eats
There’s something magical about Sleepy Hollow in the fall. Between the colorful foliage, historic cemeteries, Hudson River views, and the legend of the Headless Horseman, it’s one of my favorite autumn day trips.
I’ve visited Sleepy Hollow and nearby Tarrytown several times, and each trip brings a new discovery. Whether you’re looking for Halloween fun, a scenic hike, or a great meal, this corner of Westchester County has plenty to offer.
And the good news? Halloween may be October 31, but the spooky fun continues into November!
Sleepy Hollow Cemetery: History & Hauntings
Immortalized in Washington Irving’s The Legend of Sleepy Hollow, this historic village embraces its spooky reputation, especially in autumn.
Sleepy Hollow Cemetery is a must-see, with winding pathways, impressive monuments, and the final resting places of notable figures, including Washington Irving himself.
Nearby stands the 17th-century Old Dutch Church, featured in Irving’s famous tale. It’s easy to imagine Ichabod Crane racing through the darkness with the Headless Horseman close behind!
Explore the cemetery during public visiting hours or book a guided tour. The evening lantern tours are particularly atmospheric, bringing local history to life by kerosene lantern light.
2026 Lantern Tours: Select evenings continue into November, including Saturdays through November 28.
Rockefeller State Park Preserve: A Fall Favorite
Just a short drive away, Rockefeller State Park Preserve offers approximately 45 miles of scenic carriage roads winding through wooded hills, meadows, and beautiful countryside.
On an earlier visit, we spotted cows grazing in a meadow, a woodpecker, and plenty of birds. With its magnificent trees and colorful foliage, it’s especially beautiful in autumn.
Whether you’re looking for a leisurely stroll or a longer hike, this is a wonderful place to explore. Dogs are welcome on leash, too!
Rockwood Hall: A Gilded Age Estate with Incredible Views
On a more recent visit, I discovered Rockwood Hall, another beautiful section of Rockefeller State Park Preserve.
And what a discovery!
Once the site of William Rockefeller’s magnificent 202-room mansion, the estate featured a landscape designed by Frederick Law Olmsted, the renowned landscape architect behind Central Park.
Although the mansion is long gone, massive stone walls, sweeping lawns, and magnificent specimen trees remain, offering a glimpse into its Gilded Age past.
But the real showstopper is the view.
From the grounds, you can look out across the Hudson River toward the Palisades. It’s absolutely breathtaking, especially when the trees are bursting with autumn color.
Standing at the overlook, it’s one of those places where you just want to stop and take it all in. If you love history, scenic landscapes, and a peaceful walk, don’t miss Rockwood Hall.
Where to Eat: How a Long Wait Led to My New Favorite
Horsefeathers | 94 North Broadway, Tarrytown
Horsefeathers has been a Tarrytown favorite since 1981, and it’s easy to see why. With its cozy tavern atmosphere, literary-inspired decor, and hearty pub food, it’s a perfect fit for Sleepy Hollow’s spooky season.
The only problem? Every time I seem to visit, there’s a long line to get in!
Don’t get me wrong, Horsefeathers is great if you can get a table. But on one particular visit, faced with an hour-long wait, I decided to try somewhere else.
And that’s how I discovered my new favorite.
Pita House | 27 North Broadway, Tarrytown
Just down the street, I stumbled upon Pita House, a casual Mediterranean restaurant that won me over with its complimentary homemade hummus and fresh pita, flavorful lentil soup, and delicious chicken shawarma platter.
My son loved his double-patty cheeseburger, and on a return visit, my friend’s shakshuka with eggplant and halloumi was another hit.
The food was so good that I returned just a week later, despite living nowhere near Tarrytown! Horsefeathers is great if you can get in, but Pita House has officially become my go-to whenever I’m in the area.
Halloween Fun Continues Into November 2026
The spooky season isn’t over just yet! Here are three reasons to plan a visit.
Sleepy Hollow Cemetery Lantern Tours | Through November 28
Explore the historic cemetery after dark while hearing fascinating stories about Washington Irving and other notable residents. Tours continue on select November evenings, including Saturdays through Thanksgiving weekend.
The Great Jack O’Lantern Blaze | Through November 8
Thousands of illuminated, hand-carved pumpkins transform Van Cortlandt Manor in nearby Croton-on-Hudson into a spectacular nighttime experience.
Dates: Select evenings through Sunday, November 8, 2026.
Location: 525 South Riverside Avenue, Croton-on-Hudson.
Advance timed tickets are required.
The Great Jack O’Lantern Blaze
Sleepy Hollow Street Fair | Sunday, November 8
10 AM–5 PM | Beekman Avenue, Sleepy Hollow
Originally scheduled for October, the popular street fair has been rescheduled to November 8!
Enjoy more than 145 arts and crafts, food, and beverage vendors, local shops, live music, and family-friendly entertainment.
And yes, the Headless Horseman will be there!
Highlights include:
- 11:30 AM & 3 PM: Witches Along the Hudson performances.
- Noon: Storytelling with Jonathan Kruk.
- 1–4 PM: Meet the Headless Horseman.
- All day: Live music, food vendors, and a Kids’ Zone.
Admission is free, and dogs are welcome.
Plan Your Visit
Sleepy Hollow and Tarrytown are approximately 25 miles north of New York City and make a wonderful day trip from Long Island.
Metro-North’s Hudson Line serves the area, although a car makes exploring the hiking destinations easier.
Popular Halloween attractions can sell out, so book tickets in advance. Visit Visit Sleepy Hollow for additional events and information.
My advice? Wear comfortable shoes, bring your camera, leave time to explore, and definitely save room for a good meal.
Whether you’re drawn by the Headless Horseman, Gilded Age history, or spectacular Hudson River scenery, Sleepy Hollow is worth visiting again and again.
Happy haunting!
Roni Jenkins is a founding partner in The Three Tomatoes. She shares her social media and digital marketing savvy with the 3Ts. She is a Mom of three young children, is actively involved in several non-profit organization, including UN Women and the National MS Society and loves to run in the mud. She is inspired by her Mom and other women who have paved the way for working moms like her to be able to balance work and life. She is co-author (with her Mom) of a humorous book of quips, “Martini Wisdom.”
