Sleepy Hollow Oktoberfest
Sleepy Hollow's 13th Annual Oktoberfest in Kingsland Point Park! Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider …
Free
25 events found.
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Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States
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Blessing of the Animals
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesBlessing of the Animals brings together furry friends, fish & fowl, snakes, bugs, zebras & elephants. Pets and people of all faiths, and no faith, are welcome! The Blessing takes …
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Rockland Beer and Food Festival
German Masonic Park 89 Western Hwy S, Tappan, NYThe Rockland Beer and Food Festival brings together the region's finest breweries and food vendors for an unforgettable weekend of flavors, fun, and festivities. This is Rockland County's BIGGEST premier …
$40 – $75 -
Postponed SUP Witches of Sleepy Hollow Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesSearching for a wicked sight? Come to Kingsland Point Park for the 6th annual SUP Witches Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join …
$8 -
Rockland Beer and Food Festival
German Masonic Park 89 Western Hwy S, Tappan, NYThe Rockland Beer and Food Festival brings together the region's finest breweries and food vendors for an unforgettable weekend of flavors, fun, and festivities. This is Rockland County's BIGGEST premier …
$40 – $75 -
Christ Church/San Marcos 186th Annual Fall Fair
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesChrist Episcopal Church in Tarrytown, where Washington Irving once worshipped, is thrilled to bring back its Fall Fair in 2025! From 10 am to 4 pm, visitors can shop for …
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SUP Witches of Sleepy Hollow Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesSearching for a wicked sight? Come to Kingsland Point Park for the 6th annual SUP Witches Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join …
$8 -
SUP Witches Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesHundreds of costumed witches, warlocks, and wizards paddle the Hudson River off Kingsland Point Park in one of Sleepy Hollow's signature Halloween traditions. On shore, "Witches Hollow" brings live music, …
Free – $10 -
Halloween Spectacular featuring Hocus Pocus
Aqueduct Keepers House 15 Walnut Street, Dobbs Ferry, NYThe Halloween fun starts the night before this season at the Aqueduct Keeper's House with the return of Friends of the Old Croton Aqueduct's Halloween Spectacular! Enjoy the games, decorations, …
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Tarrytown Tree Lighting and Holiday Festivities
Patriots Park Patriots Park, Tarrytown, NY, United StatesPatriots Park in Tarrytown comes alive on December 6 with the village’s annual Holiday Kickoff, a cozy, family-friendly celebration that blends the charm of the season with the community’s creative …
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Christ Church Christmas Concert and Holiday Market
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesAnnual Christmas Concert and Holiday Market. Enjoy performances by the Choir of Christ Church San Marcos and other musical performers! Feast on bake sale items and shop the gift sale. …
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Tarrytown and Sleepy Hollow Winter Stroll
Main Street, Tarrytown Main Street, Tarrytown, NY, United StatesPhoto by Jessie Spellman Mignone. Join us for a magical evening at the Tarrytown and Sleepy Hollow Winter Stroll! Experience the charm of the season as our historic towns come …
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Hanukkah Laser Light Show
The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United StatesThis year, celebrate Hanukkah with a dazzling Festival of Laser Light, while bringing the Hanukkah story to life for all ages. You’ve never seen a Laser show like this! With …
$10 – $16 -
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Christ Church Spring Fling
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesCelebrate the arrival of spring with live jazz, refreshments, a silent auction, raffles, and fun! All proceeds benefit Christ Church San Marcos outreach in the local community and around the …
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The Pinkster Festival
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJoin Philipsburg Manor for a day filled with art, poetry, live music, dance, and storytelling that celebrates and commemorates the region’s African American history and culture. Pinkster (the Dutch word …
Free – $14 -
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Historical Society Strawberry Festival
The Historical Society, Inc. of Sleepy Hollow & Tarrytown 1 Grove Street, Tarrytown, NY, United StatesMark your calendar for a slice of pure Americana! Now in its 59th year, the Historical Society Strawberry Festival is one of the our most beloved summer traditions — a …
$10 -
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Sleepy Hollow Mermaid Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesMOVED TO RAIN DATE: SUNDAY JULY 19th Celebrate the magic of the Hudson River at the Sleepy Hollow Mermaid Festival! Located in Sleepy Hollow’s breezy Kingsland Point Park, this vibrant local …
Free – $10 -
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Fall Crafts at Lyndhurst
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesTwo hundred makers, three days, and 67 acres of Hudson River lawn to wander when you're done shopping. Artrider's longest-running craft festival returns to Lyndhurst on the third weekend of …
$6 – $16 -
Fall Crafts at Lyndhurst
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesTwo hundred makers, three days, and 67 acres of Hudson River lawn to wander when you're done shopping. Artrider's longest-running craft festival returns to Lyndhurst on the third weekend of …
$6 – $16 -
Fall Crafts at Lyndhurst
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesTwo hundred makers, three days, and 67 acres of Hudson River lawn to wander when you're done shopping. Artrider's longest-running craft festival returns to Lyndhurst on the third weekend of …
$6 – $16 -
Canceled Sleepy Hollow Oktoberfest
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesGerman food and beer, live Bavarian music, and the Hudson at your back — Sleepy Hollow's Oktoberfest returns for its 14th year. Local eateries and food trucks serve up bratwurst, …
Free – $5 -
Canceled Sleepy Hollow Street Fair
Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United StatesFree -
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Sleepy Hollow Music Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesEleven bands on two stages, a costume parade, and the Headless Horseman galloping past the stage between sets — the third annual festival that opens Sleepy Hollow's Halloween season. Main …
$62.5 – $185 -
The Sailhouse Oyster Fest
The Sailhouse 238 Green Street, Tarrytown, NY, United StatesThis October, The Sailhouse puts its own waterfront spin on the season with Oyster Fest, a series of four Sunday afternoons of fresh oysters, seasonal cocktails, and live music on …
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Blessing of the Animals
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesCelebrate the Blessing of the Animals at Christ Church! Furry friends, fish & fowl, snakes, bugs, and every creature in between are welcome — pets and people of all faiths, …
Free
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.