Rotary Rubber Duck Derby

Patriots Park Patriots Park, Tarrytown, NY

The Rotary Club of the Tarrytowns is excited to celebrate its 15th Annual Rubber Ducky Derby at Patriot’s Park on April 30th in collaboration with the YMCA Healthy Kids Day. …

Free

Historical Society Strawberry Festival

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

The 55th annual Historical Society strawberry festival is a hometown tradition! Come enjoy strawberry shortcake, ice cream, iced tea and lemonade on the society's lawn. It's like a Norman Rockwell …

$8

Westminster Kennel Club: Masters Agility Championship

Lyndhurst 635 South Broadway, Tarrytown, NY

Agility is a timed competition that tests a dog’s ability to complete an obstacle course following the commands of its handler. Purebred and All-American (mixed breed) dogs are eligible, to …

$12.5 – $30

Tarrytown Dogs on Parade

Patriots Park Patriots Park, Tarrytown, NY

The Village of Tarrytown together with the Tarrytown/ Sleepy Hollow Chamber of Commerce and Bark and Meow invite you to join Tarrytown Dogs on Parade. With the 146th Annual Westminster Kennel …

Free

Westminster Kennel Club: Breed Judging and Group Judging

Lyndhurst 635 South Broadway, Tarrytown, NY

Breed judging Judging of Toy, Terrier, and Non-Sporting breeds and Junior Showmanship Preliminaries 8:00am – 4:30pm Junior Showmanship is a competition assessing the handling skills of children 9-18 years of age-independent …

$12.5 – $25

Westminster Kennel Club: Best in Show

Lyndhurst 635 South Broadway, Tarrytown, NY

Breed Judging Judging of Sporting and Working breeds and Junior Showmanship Preliminaries 8:00am – 4:30pm Junior Showmanship Finals 7:00pm-7:30pm Group Judging Judging of Sporting, Working, and Terrier Groups ​​​​​​​7:30pm – …

$12.5 – $25

J. P. Doyle’s Annual VIP Block Party

J. P. Doyle's 48 Beekman Avenue, Sleepy Hollow, NY

J. P. Doyle's Annual Block Party marks the unofficial start to Sleepy Hollow's Halloween season. VIP tickets include priority seating for 4 live band performances, premium bar, J. P. Doyle's …

$150

Oktoberfest

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY

Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider and hot chocolate is offered for the younger set, …

Free

Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

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

Rivertowns SUP & Yoga Witch Festival

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

October lovers and Sleepy Hollow enthusiasts BE WARNED… SUP Witches are coming!! Vendors, food, brews and spooky views… it’s going to be wicked! …with “The Legend of Sleepy Hollow” told …

Free
Recurring

Sleepy Hollow Block Party

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

Live music, food trucks, entertainment for the whole family! Dance the night away at the annual Sleepy Hollow Block Party before or after the Sleepy Hollow Haunted Hayride! Beekman Avenue from Washington …

Free

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.