Exploring Sleepy Hollow, NY: Halloween Haunts, Attractions, Events & More

Exploring Sleepy Hollow, NY

While Sleepy Hollow is often thought of as a Halloween town, there are so many other things to see and do in this village as well in nearby Tarrytown.

The area is the location of Kykuit, the former home of the Rockerfeller family, and the recently opened David Rockefeller Creative Arts Center where you enjoy performances, art, tours, and more. For Halloween, you and your family can enjoy tons of Halloween events and attractions like the SUP Witches Festival, tour of the historic Octagon House, Glass Pumpkin Patch, and so much more! You can also view Washington Irving’s “The Legend of Sleepy Hollow,” take a guided cemetery tour, see a performance of Irving’s Legend at his former home in Sunnyside, or view the Headless Horseman Statue.

Check out more below to help you plan your day trip to Sleepy Hollow.

Take a road trip to another town in Westchester with a visit to Ossining, NY.

Sleepy Hollow Food/Drinks

Bridge View Tavern

Enjoy pub-style fare with specialty burgers, sandwiches, tacos, chili, and as well as an extensive beer menu. 226 Beekman Ave, Sleepy Hollow, NY 10591

Hudson Farmer & The Fish Restaurant

Located on the Riverwalk in Sleepy Hollow, enjoy a selection of farm specialities, a raw bar, pizza, and seafood classics. 11 River St, Sleepy Hollow, NY 10591.

Hudson Anchor Restaurant

This restaurant boosts a rooftop as well as outdooor and indoor seating. A seafood-forward menu, you can also find burgers and pasta. 222 Beekman Ave, Sleepy Hollow, NY 10591

Sleepy Hollow & Tarrytown Attractions

Hudson Valley Writers Center 

Budding and established writers can take classes and establish community at this prolific writing center. Classes are offered for kids and adults as well as one-day workshops. Hudson Valley Writers Center, 300 Riverside Drive, Sleepy Hollow, NY 10591. 

Kingsland Park

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. 299 Palmer Avenue, Sleepy Hollow, NY 10591.

Philipsburg Manor

Visit Philipsburg Manor from May to November to learn more about Colonial America and its enslaved inhabitants. They host guided tours from Friday-Sunday between 10:30am-3:30pm where you can see the location that was home this milling and trading complex that 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. Philipsburg Manor, 381 North Broadway, Sleepy Hollow, NY.

Headless Horseman Statue
Headless Horseman Statue in Sleepy Hollow.

Headless Horseman Statue

See the 18-foot Headless Horseman and Ichabod Crane statue on route 9 between the Philipsburg Manor restoration and the Old Dutch Church. Unveiled in 2006, the statue is great for photos as you admire the craftsmanship and scenic backdrop. 362 Broadway, Sleepy Hollow, NY 10591.

Kykuit, The Rockerfeller Estate

Take a tour of Kykuit, the former hilltop mansion of four generations of the Rockefeller family. Tours are avaiable from May-November 13th where you will see this incredible home with its gorgeous views. Tour are held on Saturday-Sunday from May 21-October 2; and Wednesday-Monday between October 5-November 13. 381 North Broadway, Sleepy Hollow, NY. 

Lyndhurst Mansion 

Take a tour of the Lyndhurst Mansion throughout the year. For the Halloween season, you and your family can take the Spirited Mansion Weekend tour where you can explore the mansion at your own pace, looking at the seasonal decorations. This includes access to the vestibule and entrance hall, reception room, parlor, library, and Victorian dining room. At the end of the tour, refreshments and snacks will be available for sale. Tickets are $24 per person. Lyndhurst Mansion, 635 South Broadway, Tarrytown, NY 10591.

Old Dutch Church

Visit the church that was 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. Old Dutch Church, 430 North Broadway, Sleepy Hollow, NY 10591.

Sleepy Hollow Lighthouse

Take a walk along the RiverWalk at the foot of Beekman Avenue for a look at the Sleepy Hollow Lighthouse that was formerly in operation for over 78 years. The former home of 12 light keepers and their families, the lighthouse stopped being used in 1961.

Tarrytown & Sleepy Hollow Farmers Market – TaSH
Every Saturday (May 28th – November 30th) from 8:30am-1:30pm

Enjoy live music, baked goods, fruits and vegetables and more. Held every Saturday in the beautiful Patriots Park, TaSH also regularly offers cooking demos, art projects, and kids’ activities. Patriots Park, U.S. 9, Tarrytown, NY.

David Rockefeller Creative Arts Center

Visit the newly opened David Rockefeller Creative Arts Center, a vibrant public venue offering local and global performances and exhibits, 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. David Rockerfeller Creative Arts Center, 200 Lake Road, Tarrytown, NY 10591.

Sleepy Hollow and Tarrytown Events

Horan’s Landing 

This waterfront park is the location of many summer concerts.  There is also a grassy area here along with a beach where you can use kayaks and paddleboards. In October, Horans’s Landing is also the location of the Rivertowns SUP and Yoga Witch Festival where you can dress like a witch and paddleboard along the Hudson. 57 River St, Sleepy Hollow, NY 10591.

September, 30th from 1:00pm-5:00pm

Families can enjoy feast of German food and beer as well as cider and hot chocolate for kids. This September fest also includes dancing to Bavarian music, live music, and more! Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY 10591.

Saturdays and Sundays from 11:00am- 12:00pm and 1:00pm – 2:00pm until November 26th. In October, every day from 1:00pm-2:00pm
The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”

Older kids and their families may enjoy this interesting cemetery tour where you will learn more about Washington Irving, his impact on American Literature and “The Legend of Sleepy Hollow.” Sleepy Hollow Cemetery, South Gate 430 North Broadway, Sleepy Hollow, NY 10591.

Friday, September 21st-Sunday, October 29th, Fridays at 7:00pm; Saturdays at 2:00pm and 7:00pm; Sundays at 2:00pm and 7:30pm
The Legend: Cirque Performance

See this Cirque adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow” with narration by Washington Irving himself, in hologram form! The event is for ages 10 and up. $30 when purchased online; $40 at the door. Westchester Circus Arts at the Village of Sleepy Hollow, 60 Continental Street, Sleepy Hollow, NY.

Myths and Mysteries Tour
Take the Myths and Mysteries Tour at the Octagon House.

Various dates and times in September and October
Myths and Mysteries Tour

Take a tour of the historic Armour-Stiner (Octagon) House to learn more about this historic home and the looming mystery that surrounds it. The tours highlights the architectural wonders of the home, such as its unique dome shape and octagonal floor plan rooted in 19th century Phrenology as well as speculations of a resident ghost. Tickets are $29 per person. The Armour-Stiner (Octagon) House, 45 West Clinton Ave, Irvington, NY 10533.

Glass Pumpkin Patch in Sleepy Hollow
Glass Pumpkin Patch

Friday, October 6th-Sunday, October 9th from 10:00am-5:00pm
Glass Pumpkin Patch

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. Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY 10591.

Irving’s ‘Legend’ at Sunnyside
Irving’s ‘Legend’ at Sunnyside

Various times until October 31st
Irving’s ‘Legend’ at Sunnyside

Listen to master storyteller Jonathan Kruk recount “The Legend of Sleepy Hollow.” This outdoor experience also includes live music from Jim Keyes as well as an appearance from the Headless Horseman. Guests can now enjoy fall-themed drinks, such as beer from Captain Lawrence, 1911’s New York state hard cider, and pumpkin spice soda, as well as fun snacks like fudge, Legend popcorn mix, and cider donuts. The museum shop, which can be visited before or after the event, is filled with souvenirs and local finds, including Legendthemed t-shirts, hats, and more. Washington Irving’s Sunnyside is at 3 West Sunnyside Lane, Irvington, one mile south of the Tappan Zee Bridge.

Sunday, October 15th from 12:00pm-4:00pm
SUP Witches Festival 

Celebrate the witchy season Sleepy Hollow style at the SUP Witch’s Festival. The 3rd annual festival features a paddle where witches take off at Horan’s Landing and paddle along the Hudson. You can also watch or stroll along the riverwalk to watch the witches pass. The event also includes local vendors, brews, and spooky views. All who are paddling must wear a costume. The event is $30 if bringing own SUP equipment (kayaks welcome) or $45 to rent SUP equipment (includes board, paddle, leash, PFD). All guests interested in participating must pre-register in advance (registration opens on September 16th). Horan’s Landing, 57 River Street, Sleepy Hollow, NY 10591.

Sleepy Hollow’s Annual Haunted Hayride  
Sleepy Hollow’s Annual Haunted Hayride  

Saturday, October 20th and Sunday, October 21st, various times
Sleepy Hollow’s Annual Haunted Hayride  

Prepare to be freaked out during the 2023 Sleepy Hollow Haunted Hayride. A long-standing tradition for over 15 years, the hayride experience includes a scary trip into the woods. There is also a block party on Beekman Avenue where you can enjoy live music, family activities and vendors before or after your haunted experience. Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591.

October 18th-21st and October 25th-28th from 6:00pm and 7:00pm
Hulda’s Night at Rockefeller State Park Preserve 

Enjoy a Halloween experience like no other with Hulda’s Night. The event starts where you walk through a path illuminated by lanterns where you will then join a traveler. Your journey continues as you listen to more stories about war and a nearby witch. Groups go down the witch’s spring trail as you are guided to Hulda’s home, eventually meeting Hulda herself who will tells your group a story. Tickets are $62.00 per person. Rockefeller State Park Preserve, 25 Sleepy Hollow Road, Sleepy Hollow, NY 10591.

Saturday, October 29th from 5:30pm-6:30pm
Rain date: October 30th
Tarrytown Halloween Parade

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!  Patriots Park, Sleepy Hollow, NY 10591.