Historical Society Preservation Award & Wine Tasting Fundraiser

The Historical Society, Inc. of Sleepy Hollow & Tarrytown 1 Grove Street, Tarrytown, NY, United States

This year's Historical Society Preservation Award & Wine Tasting honors Margo & Don Stever and The Hudson Valley Writers Center for their efforts to preserve the former Hudson River Railroad Station in Philipse Manor. The Stevers are long-time supporters of local history and the literary heritage of the community. Enjoy a selection of wine and spirits …

$100 – $125

Headless Horseman Ball

Castle Hotel & Spa 400 Benedict Avenue, Tarrytown, NY, United States

Welcome to a night of spine-tingling excitement at the Castle Hotel & Spa's Headless Horseman Ball! This unique event, scheduled for Friday the 13th of October, 2023, promises an unforgettable experience filled with mystery, suspense, and lots of fun. The Headless Horseman Ball is a night like no other, where guests are encouraged to tap …

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.