Oktoberfest
Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider and hot chocolate is offered for the younger set, music and entertainment for all ages!
Free
25 events found.
Sponsored
Events
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Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States
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The Legend Cirque
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesThe Legend Cirque is back by popular demand for a second season. Step into the magic of the Big Top and witness The Legend of Sleepy Hollow come to life in a haunting display of acrobatic feats. Ichabod Crane and Brom Bones compete for Katrina Van Tassel's hand, and the Headless Horseman returns in a …
$45 – $50 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 174-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …
$27.5 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJoin master illusionists Mark Clearview and Nick Wallace as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda of Bohemia, British spy Major John André, and the Headless Horseman himself! Once …
$65 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesThe Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! 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. New for 2023, see the twirling pumpkin Ferris wheel …
$24 – $129 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesIrving’s Legend returns reimagined this fall. Performed under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages! Advance reservations are required. No tickets will …
$40 – $45 -
The Legend Cirque
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesThe Legend Cirque is back by popular demand for a second season. Step into the magic of the Big Top and witness The Legend of Sleepy Hollow come to life in a haunting display of acrobatic feats. Ichabod Crane and Brom Bones compete for Katrina Van Tassel's hand, and the Headless Horseman returns in a …
$45 – $50 -
Tito Puente, Jr. Latin Jazz Ensemble
Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United StatesHe’s the son and musical heir of “El Rey” – The King – the legendary American salsa and Latin jazz maestro Tito Puente. Tito Puente Jr. is certainly a prince, honoring his father's legacy with a hot ensemble and playing with the same joy, becoming an audience favorite in casinos, performing arts centers, symphony halls, …
$35 – $40 -
The Good, the Bad and the Unusual-Cemetery Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesJoin Sara Mascia and Tara Van Tassell from our local historical society as they dish about several intriguing locals as well as some of Sleepy Hollow Cemetery's world-famous inhabitants. You can guess who will be good, bad, or unusual! Among the many locals are poet and eccentric Minna Irving, chocolatier William Wallace, and popular neighbor …
$46 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJoin master illusionists Mark Clearview and Nick Wallace as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda of Bohemia, British spy Major John André, and the Headless Horseman himself! Once …
$65 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe true stories on this two-hour lantern tour of Sleepy Hollow Cemetery are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his …
$50 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesIrving’s Legend returns reimagined this fall. Performed under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages! Advance reservations are required. No tickets will …
$40 – $45 -
The Princess Bride: An Inconceivable Evening with Cary Elwes
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesJoin Cary Elwes (Westley) for a behind-the-scenes look at life on and off the set of the classic film, The Princess Bride. After a screening of the iconic movie, Elwes takes the Tarrytown Music Hall stage for a moderated discussion revealing never before shared secrets and tales of inconceivable antics! A limited number of VIP …
$38 – $150 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep 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. You’ll visit titans of industry like Andrew Carnegie and William Rockefeller, meet Washington Irving whose famous short story gave our village its very name, see the …
$46 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJoin master illusionists Mark Clearview and Nick Wallace as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda of Bohemia, British spy Major John André, and the Headless Horseman himself! Once …
$65 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesIrving’s Legend returns reimagined this fall. Performed under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages! Advance reservations are required. No tickets will …
$40 – $45 -
Tito Puente, Jr. Latin Jazz Ensemble
Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United StatesHe’s the son and musical heir of “El Rey” – The King – the legendary American salsa and Latin jazz maestro Tito Puente. Tito Puente Jr. is certainly a prince, honoring his father's legacy with a hot ensemble and playing with the same joy, becoming an audience favorite in casinos, performing arts centers, symphony halls, …
$35 – $40 -
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Irvington Farmers Market
Main Street School 101 Main Street, Irvington, NY, United StatesEnjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh local produce, seafood and meats, cheese, pickles, prepared foods and baked goods. The market is just a short distance from Washington Irving’s home Sunnyside. Look …
Free -
Lyndhurst Tours
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesLyndhurst, one of America’s finest Gothic Revival mansions, overlooks the Hudson River in Tarrytown, NY. The estate was shaped for more than a century by three families and their staff: The Pauldings, The Merritts, and the Goulds. Their influence is evident in the expansion of the main house from a country villa to a Gothic mansion, …
$18 – $42 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 174-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …
$27.5 -
Lyndhurst Fall Classic Mansion Tour
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesPerfect for first-time guests, this one-hour tour covers two floors and treats visitors to a rare glimpse of the lavish decorative arts and furniture left to Lyndhurst by previous owners all while decorated with the splendor of the Fall Season! The tour, which lasts an hour, visits approximately 16 rooms and involves climbing one staircase. …
$20 – $28 -
Home of the ‘Legend’
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesAt this family-friendly happening, visitors can tour Washington Irving’s house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how "The Legend of Sleepy Hollow" has lived in the imagination of popular culture through the centuries since its publication. 2023 Select Dates: September 15 - November 5.
$15 – $18 -
Kykuit Tours
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesBuilt between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family. In 2023 the site will be open for guided walking tours Friday-Sunday from May 12-October 1; and Wednesday-Monday between October 4-November 12. Also open Memorial Day, July 3 & 4, Labor Day, and Columbus Day. There are three distinct Kykuit …
$20 – $65 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of “The Legend of Sleepy Hollow”, which recently celebrated its Bicentennial. Best of all, …
$20 -
Octagon House Myths and Mysteries Tour
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States18 miles north of New York City, high on a bank along The Hudson River sits The Armour-Stiner (Octagon) House. Built in 1860, this enigmatic, eight-sided, domed landmark is the pride of the Village of Irvington, in the heart of Sleepy Hollow Country. During the month of October, The Octagon House celebrates the Halloween season …
$29
There's something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.