Meandering Among Mansions of Millionaires

Irvington Theater 85 Main Street, Irvington, NY

Take an after-lunch stroll on the Aqueduct Trail. Meet at Irvington’s Town Hall at 85 Main Street, less than ½ mile east up Main Street from the Irvington Metro-North train …

Free

Anaïs Mitchell and Bonny Light Horseman

Tarrytown Music Hall 13 Main Street, Tarrytown, NY

Anaïs Mitchell, the esteemed singer-songwriter whose Broadway smash "Hadestown" won 8 awards, including Best Musical, at the 2019 Tony Awards, is joined on this one-of-a-kind tour by Bonny Light Horseman, …

$38 – $48

Sunset Hike at Rockwood Hall

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY

Join a 3-mile sunset hike at Rockwood Hall for what, weather permitting, will be a spectacular view over the Hudson and the Tappan Zee Bridge. Please dress according to weather …

$3

Trey Kennedy: The Are You For Real? Tour

Tarrytown Music Hall 13 Main Street, Tarrytown, NY

Trey Kennedy is a born and raised Oklahoman who never expected to enter the entertainment industry. While attending college at Oklahoma State University, Trey found fame on the mobile app Vine, amassing more than …

$39 – $59
Recurring

Ken Peplowski Quartet featuring Pasquale Grasso

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

The Ken Peplowski Quartet featuring Ken Peplowski, Sax, Clarinet; Pasquale Grasso, guitar; Mike Karn, bass and Phil Stewart, drums. One of jazz’s top clarinetists, Ken Peplowski has been a touring headliner for …

$25 – $30
Recurring

Ken Peplowski Quartet featuring Pasquale Grasso

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

The Ken Peplowski Quartet featuring Ken Peplowski, Sax, Clarinet; Pasquale Grasso, guitar; Mike Karn, bass and Phil Stewart, drums. One of jazz’s top clarinetists, Ken Peplowski has been a touring headliner for …

$25 – $30
Recurring

Ken Peplowski Quartet featuring Pasquale Grasso

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

The Ken Peplowski Quartet featuring Ken Peplowski, Sax, Clarinet; Pasquale Grasso, guitar; Mike Karn, bass and Phil Stewart, drums. One of jazz’s top clarinetists, Ken Peplowski has been a touring headliner for …

$25 – $30
Recurring

Ken Peplowski Quartet featuring Pasquale Grasso

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

The Ken Peplowski Quartet featuring Ken Peplowski, Sax, Clarinet; Pasquale Grasso, guitar; Mike Karn, bass and Phil Stewart, drums. One of jazz’s top clarinetists, Ken Peplowski has been a touring headliner for …

$25 – $30
Recurring

Old Croton Aqueduct Weir Tour

Joseph G. Caputo Community Center 95 Broadway, Ossining, NY

The Old Croton Aqueduct, New York City's original water supply, runs from, Croton-on-Hudson into the Bronx and Manhattan, passing through Sleepy Hollow and Tarrytown. For most of its length, the Aqueduct …

Free

Al Franken – The Only Former US Senator Currently On Tour Tour

Tarrytown Music Hall 13 Main Street, Tarrytown, NY

As far as anyone knows, Al Franken is the only U.S. Senator who was also one of the original writers for Saturday Night Live. During his fifteen seasons with SNL, Franken …

$59 – $129

There’s something for everyone in the real Sleepy Hollow—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 5K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.