Tarrytown Street Fair

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Tarrytown Street Fair takes place this year on Sunday, June 4th. Main Street transforms into an outdoor market with food, music, local retailers, arts & crafts, souvenirs and more! Explore more local shopping at Tarrytown's and Sleepy Hollow's galleries, gift shops and antique stores. Rain date: Sunday, June 2, …

Free

Event Series Open Streets Tarrytown

Postponed Open Streets Tarrytown – Mother’s Day

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The Village will be closing down Main Street to cars and opening it up to shopping, dining, strolling, and more on three Sundays this year. Come out to celebrate Mom on Mother's Day with outdoor dining, live music in the streets, a family selfie booth and more! "Mom & Me Selfie" Station by the mural …

Free

St. Patrick’s Day Parade

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The 28th annual Tarrytown and Sleepy Hollow St. Patrick's Day Parade steps off at 1:30pm on Main Street in Tarrytown and proceeds north on Route 9 (Broadway) to Beekman Avenue in Sleepy Hollow. Bring your green, the kids, the dogs and have fun!!! Dogs MUST be leashed at all times.

Free

Tarrytown Street Fair

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Tarrytown Street Fair takes place this year on Sunday, June 4th. Main Street transforms into an outdoor market with food, music, local retailers, arts & crafts, souvenirs and more! Explore more local shopping at Tarrytown's and Sleepy Hollow's galleries, gift shops and antique stores.

Free

St. Patrick’s Day Parade

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The 27th annual Tarrytown and Sleepy Hollow St. Patrick's Day Parade steps off at 1:30pm on Main Street in Tarrytown and proceeds north on Route 9 (Broadway) Beekman Avenue in Sleepy Hollow. Plenty of toys (for sale) for the kids! Dogs welcome but MUST be leashed at all times!

Free

Event Series Winter Stroll

Tarrytown and Sleepy Hollow Winter Stroll

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

Kick off the Holiday season on December 3rd with the second annual Tarrytown and Sleepy Hollow Winter Stroll!  Extended shopping hours, outdoor dining, story telling, trolleys, holiday treats, carolers, ugly sweater contest, live entertainment and other special events! 2022 date: December 3. 5 pm tp 9 pm. Where: Main Street, Tarrytown, NY 10591 For info: https://www.sleepyhollowtarrytownchamber.com …

Free

Tarrytown/Sleepy Hollow St. Patrick’s Day Parade

Main Street, Tarrytown Main Street, Tarrytown, NY, United States

The 26th annual parade steps off at 1:30pm on Main Street in Tarrytown and proceeds north on Route 9 (Broadway) Beekman Avenue in Sleepy Hollow. Plenty of toys (for sale) for the kids! Dogs welcome but MUST be leashed at all times!

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.