Sleepy Hollow Offers Fall Fun for Everyone
Take a trip to the historic town of Sleepy Hollow for autumn delights and spooky thrills!
While New York City is filled with plenty of frights and fiends, there’s nothing like taking a road trip close to home to appreciate what the state has to offer.
Known for its lore and the legend of the headless horseman, many families flock to the town of Sleepy Hollow during the fall to celebrate the start of spooky season.
Just a short one-hour drive from the city, Sleepy Hollow offers tons of Halloween and seasonal fun for families of all ages, from dining and creative drinks, to attractions including writer’s centers, nature-filled parks with beautiful fall foliage, to historic mansions and churches. There’s no shortage of things to do, so prepare your best walking shoes and favorite costumes and get ready for the beauty that is Sleepy Hollow.
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Places to Eat & Drink
226 Beekman Ave.
(914) 332-0078
Enjoy pub-style fare with specialty burgers, sandwiches, tacos, chili, and as well as an extensive beer menu.
Horsefeathers
94 North Broadway
(914) 631-6606
Bordering Sleepy Hollow in the neighborhood of Tarrytown and around since 1981, Horsefeathers has been a staple in the village of Tarrytown, offering both classic and New American cuisine. Nestled along Route 9, visitors can dine on delicious New England clam chowder, chicken cutlet, Irish nachos, and more while enjoying local legends celebrating the rich history and lore of Sleepy Hollow Country.
Hudson Farmer & The Fish Restaurant
11 River St.
(914) 631-8380
Located on the Riverwalk in Sleepy Hollow, this restaurant offers a selection of farm specialties, a raw bar, pizza, and seafood classics.
Things to Do
300 Riverside Dr.
(914) 332-5953
Budding and established writers can take classes and establish a community at this prolific writing center. Classes for kids and adults are offered, as well as one-day workshops.
299 Palmer Ave.
(914) 366-5109
This 18-acre park offers some incredible views of the Hudson River and historic Tarrytown Lighthouse. It is also home to a small playground and has picnic areas, ballfields, hiking trails, and fishing docks, perfect for a day of outdoor family fun.
381 North Broadway
(914) 366-6900
Visit Philipsburg Manor from May to November to learn more about Colonial America and its enslaved inhabitants. They host guided tours from Friday to Sunday between 10:30 am and 3:30 pm, during which you can see the location that was home to this milling and trading complex, which was also home to 23 enslaved Africans. The home includes artifacts and reproductions. In the activity center, you can learn more about the daily life and labor of those who lived in the Manor.
Visit the Headless Horseman Statue
362 Broadway
See the famous 18-foot Headless Horseman and Ichabod Crane statue on Route 9 between the Philipsburg Manor restoration and the Old Dutch Church. Unveiled on Halloween day in 2006, the statue is great for photos as you admire the craftsmanship and scenic fall backdrop of the town’s most famous lore.
Take a Tour of Kykuit, The Rockefeller Estate
381 North Broadway
(914) 366-6900
Take a tour of Kykuit, the former hilltop mansion of four generations of the Rockefeller family. Tours are available from May to November 13th, and you will see this incredible home with its gorgeous views. Tours are held on Monday, Wednesday, and Friday through Sunday from October 1st to November 9th. Tickets start at $75 for adults and $20 for children aged 10-17.
35 South Broadway
(914) 303-6838
For all things autumn, take your family on a decorated journey with the Fall Classic Mansion Tour, where you can explore the mansion at your own pace and revel in awe at the beautiful seasonal decorations. For those looking for a more haunting experience, tickets for Gothic Weekend 2025 are available for purchase and feature tarot readings and a collection of Hudson Valley vendors that will sell an eclectic mix of spooky oddities, curated antiques, gothic jewelry, and witchy wares. Seasonal food offerings will also be available to satisfy your autumnal cravings.
430 North Broadway
Step into history with a visit to the church featured in Washington Irving’s “The Legend of Sleepy Hollow” and supposed home of the headless horseman. They host tours, such as the Tarryhollow: Irving, the Old Dutch Church, and the Colonial Experience, or you can take a self-guided tour.
Catch a View from the Sleepy Hollow Lighthouse
Tarrytown Light-Kingsland Point Path
Take a walk along the RiverWalk at the foot of Beekman Avenue to see the Sleepy Hollow Lighthouse, which was in operation for over 78 years. The former home of 12 lightkeepers and their families, the lighthouse went out of use in 1961.
Get Fresh Picks from Tarrytown & Sleepy Hollow Farmers’ Markets – TaSH
Patriots Park, U.S. 9
Saturdays 8:30 am to 1:30 pm to November 22nd
Enjoy live music, baked goods, fresh fruits, and vegetables as you enjoy the crisp fall air in Patriots Park in the neighboring town of Tarrytown. Held every Saturday in the beautiful Patriots Park, TaSH also regularly offers cooking demos, art projects, and kids’ activities. This year, a special Halloween market will be held on October 26th, perfect for some last-minute pumpkin-carving.
Get Creative at The David Rockefeller Creative Arts Center
200 Lake Rd.
(914) 524-6560
A vibrant public venue offering local and global performances and exhibits, the center offers residencies for visual, performing, and literary artists, and a space for cultural events. Located inside The Pocantico Center in Tarrytown (on the former Rockefeller family estate), the location is housed in John D. Rockefeller’s historic 1908 Orangerie, which has been completely transformed by architects to include a performance space, gallery, and artists’ studio. Check out the complete calendar of fall events at Pocantico at rbf.org/events. All visitors have to reserve tickets in advance.
Sleepy Hollow and Tarrytown Events
The Great Jack O’Lantern Blaze
Sept. 12 to Nov. 16
Meander through the 18th-century landscape of Van Cortlandt Manor and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site by a team of talented artisans. Complete with lighting and music, visitors can also spot iconic New York landmarks carved in pumpkins, stroll the Pumpkin Promenade to see new themed displays each week, indulge in your inner circus for a big top adventure made of jack o’lanterns, and more.
Sleepy Hollow Cemetery Lantern Tour
Every night in October and select nights in November
Step back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous.
An Audience with Poe
October 3 to November 1, performances Fridays-Sundays plus Columbus Day Monday. Times vary.
professional storytellers bring to life the “powerful graphic effect” that Washington Irving once praised in Edgar Allan Poe’s writing, with haunting renditions of The Raven, The Tell-Tale Heart, The Black Cat, and The Masque of the Red Death. We pair the tales with complementary cocktails or mocktails designed to capture the spirit of the stories.
Oktoberfest at Kingsland Point Park
Sept. 27, 1 pm to 5 pm
Families can enjoy a feast of German food and beer, as well as cider and hot chocolate for kids. This Septemberfest also includes dancing to Bavarian music, live music, and more!
Oct. 2-5, 10 am to 5 pm
Experience the artistry of a glass pumpkin patch from artist Gregory Tomb in partnership with Make-A-Wish® Hudson Valley for this inaugural event. The festival will showcase over 1,000 whimsical and vibrantly colored glass pumpkins, all handmade by Gregory, which will be available for purchase. The proceeds will support Make-A-Wish® Hudson Valley to support children in the Hudson Valley region who have critical illnesses.
Oct. 26, 5 pm to 6 pm
Dress up with your kids and enjoy the 20th annual Village of Tarrytown Halloween Parade. Participate with a theme as a group or float for a chance to win prizes. The parade features a route from along Broadway to Tarrytown’s Main Street. After the parade, enjoy a block party with a DJ and live music, outdoor dining, performers, and much more!
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