Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 8th, transforming Beekman Avenue into an outdoor market. October is the most exciting …

Free
Event Series Home of the ‘Legend’

Home of the ‘Legend’

Sunnyside 3 W Sunnyside Lane, Irvington

At 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 …

Free – $12
Event Series Octagon House Classic Tour

Octagon House Classic Tour

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington

The 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, …

$29
Event Series Kykuit Tours

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow

Built 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; …

$18 – $60
Event Series Philipsburg Manor Tours

Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow

Journey 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 …

$12 – $17
Event Series Union Church Tours

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow

The 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 …

$9

Violent Femmes

Tarrytown Music Hall 13 Main Street, Tarrytown

Violent Femmes formed in 1981 as an acoustic punk band playing on the streets of Milwaukee, Wisconsin. Their main influences at that time were Gene Vincent and the Blue Caps …

$64 – $84

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.