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 Theatre Performance
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesStep back in time. It’s the 1800’s. Hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The LEGEND is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – …
$30 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 173-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 …
$25 -
The Legends of The Legend of Sleepy Hollow
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesHear Master Storyteller Jonathan Kruk spin the haunting tales of the ghost surrounding the Headless Horseman and the galloping goblin's origin story! Tarrytown and Sleepy Hollow have long hosted several famed spirits: Tragic Major Andre the spy who conspired with the traitorous Benedict Arnold, The Wailing Woman in White, Ship-sinking Imps on the Hudson River, Hulda the …
$20 -
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 2022, watch the animated “Jack” Smith Shop …
$24 – $99 -
The Legends of The Legend of Sleepy Hollow
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesHear Master Storyteller Jonathan Kruk spin the haunting tales of the ghost surrounding the Headless Horseman and the galloping goblin's origin story! Tarrytown and Sleepy Hollow have long hosted several famed spirits: Tragic Major Andre the spy who conspired with the traitorous Benedict Arnold, The Wailing Woman in White, Ship-sinking Imps on the Hudson River, Hulda the …
$20 -
The Legend – Cirque Theatre Performance
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesStep back in time. It’s the 1800’s. Hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The LEGEND is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – …
$30 -
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 …
$35 -
Al Di Meola
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesAl Di Meola, a bonafide living Guitar Legend inducted into the Gallery of Greats is among the top guitarists of our time. His ongoing fascination with complex rhythmic syncopation combined with provocative lyrical melodies and sophisticated harmony has been at the heart of his music throughout a celebrated career that has spanned four decades and …
$64 – $84 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesSoak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including William Rockefeller, Andrew Carnegie, John Dustin Archbold and others resting in peace in the cemetery's north end. As this is only a one-hour tour, you’ll …
$45 -
American Aristocrats Cemetery Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesShort on time? Make the most of it and meet the crème de la crème on this one-hour lantern tour of Sleepy Hollow Cemetery! The Gilded Age began after the Civil War and ended around 1900. It was a time of tremendous industrialization and rapid economic growth. Railroads were built to connect the East Coast …
$30 -
We ARE: Aaron Goldberg, Reuben Rogers and Eric Harland
Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United StatesWe ARE is the resurgence of the long-standing collaboration of Aaron Goldberg, Reuben Rogers, and Eric Harland. Over the course of more than two decades, this eclectic trio has fine tuned their individual sounds which will be cumulatively highlighted on a new release in 2023.
$25 – $30 -
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. Sundays, 9 am to 1:30 pm rain or shine. Well behaved dogs are …
Free -
Lyndhurst Ramble Tour
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesIn celebration of the Hudson River Valley Ramble, Lyndhurst offers a walking tour of the historic estate, a Gothic Revival masterpiece overlooking the Hudson River. The site reflects over 180 years of life on the Hudson River covering 67 park-like acres. You will visit the unglazed Lord & Burnham steel-framed greenhouse and enter both the oldest …
$30 -
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.
Free – $12 -
Octagon House Classic Tour
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesThe Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …
$29 -
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 2022 the site will be open for guided tours Saturday-Sunday from May 21-October 2; and Wednesday-Monday between October 5-November 13. There are three distinct Kykuit tours available: Classic Tour: Great for first-time visitors. Your visit will include the main floor of …
$18 – $60 -
Philipsburg Manor Tours
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJourney to Colonial America! Wander along a woodland path and enter the year 1750, when Philipsburg Manor was a thriving milling and trading complex that was home to several hundred tenant farmers and twenty three enslaved individuals of African descent. Step into the gristmill and learn about the work of Caesar, the enslaved African miller. Tour …
$12 – $17 -
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, …
$15 -
Geology of the Hudson Valley
Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United StatesJoin environmental educator, Kim Fendrich, on a journey through time. Learn about the geologic history of this area and observe evidence of tectonic activity, glaciation, weathering, and erosion throughout the Preserve. You will begin with a demonstration to put Earth’s 4.5 billion year history into perspective, followed by discussion and then a short walk to …
$3 -
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 is pleased to announce …
$29 -
Union Church Tours
Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow, NY, United StatesThe Union Church of Pocantico Hills is a repository of awe-inspiring art by Matisse & Chagall. Stained-glass windows by European masters, commissioned by the Rockefeller family, adorn this unassuming country church. Henri Matisse’s last work, the Rose Window, and nine windows by Marc Chagall create a dramatic combination of light and color, art and spirituality. …
$9 -
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, …
$15 -
The Legends of The Legend of Sleepy Hollow
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesHear Master Storyteller Jonathan Kruk spin the haunting tales of the ghost surrounding the Headless Horseman and the galloping goblin's origin story! Tarrytown and Sleepy Hollow have long hosted several famed spirits: Tragic Major Andre the spy who conspired with the traitorous Benedict Arnold, The Wailing Woman in White, Ship-sinking Imps on the Hudson River, Hulda the …
$20 -
The Legend – Cirque Theatre Performance
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesStep back in time. It’s the 1800’s. Hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The LEGEND is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – …
$30
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.