Sleepy Hollow Music Festival
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 …
$62.5 – $185
10 events found.
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Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States
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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 …
Free -
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 -
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, …
$8 – $35 -
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 …
Free -
Christ Church/San Marcos Annual Fall Fair
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesChrist 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 …
Free -
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 …
Free -
Food Truck Friday
Sleepy Hollow River Walk Park Westward Drive, Sleepy Hollow, NY, United StatesKick 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 …
Free -
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. After being postponed due to weather, the Sleepy Hollow …
Free – $5 -
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 …
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.