Sponsored
Festivals
Events
Calendar of Events
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Eleven 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 Stage brings the 90s: Everclear, the Smithereens featuring Marshall Crenshaw, Fastball, SoulShine: An Allman Brothers Experience, and Anthony Giaccio & the Assortments. The Regional Stage …
$62.5 – $185
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2 events,
This 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 the banks of the Hudson River. Set against sweeping views of the Governor Mario M. Cuomo Bridge, the festival pairs the laid-back marina atmosphere The …
Free
Celebrate 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, and no faith, are invited to join this joyful, rain-or-shine tradition marking the Feast of St. Francis of Assisi. The Blessing takes place in front …
Free
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Hundreds 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, food, local brews, and vendors; on the water, a mass costumed paddle launches in the early afternoon for a group photo taken mid-river. It's been …
$8 – $35
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1 event,
This 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 the banks of the Hudson River. Set against sweeping views of the Governor Mario M. Cuomo Bridge, the festival pairs the laid-back marina atmosphere The …
Free
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Christ Church San Marcos, the historic Episcopal parish in Tarrytown where Washington Irving once worshipped, brings back its beloved Fall Fair on October 17, 2026, from 10 am to 4 pm — free and open to all. Now in its 187th year, the fair is one of Sleepy Hollow Country's longest-running community traditions, tracing back …
Free
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1 event,
This 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 the banks of the Hudson River. Set against sweeping views of the Governor Mario M. Cuomo Bridge, the festival pairs the laid-back marina atmosphere The …
Free
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Kick off your weekend with great food, community, and seasonal fun along the river! Delicious Eats: A lineup of local food trucks plus sweet treats from Jimmy’s Soft Serve ice cream. Adult Beverages: Enjoy drinks on-site by Captain Lawrence Brewing Co. Live Music: Rock out to tunes by Might and the Weevils. Family Fun: Kids' …
Free
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2 events,
This 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 the banks of the Hudson River. Set against sweeping views of the Governor Mario M. Cuomo Bridge, the festival pairs the laid-back marina atmosphere The …
Free
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German food and beer, live Bavarian music, and the Hudson at your back — Sleepy Hollow's Oktoberfest returns for its 14th year. After being postponed due to weather, the Sleepy Hollow Oktoberfest is back on Sunday, October 25th, at Kingsland Point Park! Enjoy an afternoon of German food, desserts, adult beverages, live music, and more along the Hudson River. This …
Free – $5
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Canceled Sleepy Hollow Street Fair
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.