Sleepy Hollow Street Fair: Everything You Need To Know | Stanton House Inn
Plaque celebrating Washington Irving and the Headless Horseman at the Sleepy Hollow Street Fair
Yep, that Sleepy Hollow of Washington Irving fame. He lived in the area and was buried in the Old Dutch Cemetery in Sleepy Hollow, by the way.
Courtesy: Doug Kerr/Flickr

Tarrytown and neighboring Sleepy Hollow are nice towns on the Hudson River that are great to poke around in on a warm autumn afternoon.


While their big draw is the Halloween season (for the obvious reason), it’s a very nice place to visit any time of the year.

The Sleepy Hollow Street Fair

blazing pumpkins at Sleep HollowIf you need an excuse to go, why not visit for the Annual Sleepy Hollow Street Fair? Every year, the Sleepy Hollow / Tarrytown Chamber of Commerce does a great job of transforming Beekman Avenue into an outdoor market. Beekman Avenue closes to cars for the weekend and fills with over 80 vendors, live music, a kids carnival and science fair, as well as plenty of great food!


Beginning at 7:00 a.m. on the morning of the Sleepy Hollow Street Fair and continuing throughout the event, Beekman Avenue will be closed to regular traffic from Broadway to Pocantico Street.


This excuse to visit Sleepy Hollow is a great way to kick-off the Fall Season (in an area that cannot be beat for its Fall activities, by the way). Especially after you’ve eaten all the oysters you can at the Norwalk Oyster Festival on Saturday.


If that’s not enough of an enticement to head over to Sleepy Hollow, there are some other activities of interest on the same day, including over at the Stone Barns Center for Food and Agriculture just a short drive away in idyllic Pocantico Hills (where I once volunteered as a Livestock Manager, by the way). A view from the top of the farm’s hills towards the Hudson and the church spires of Tarrytown alone is worth the visit.


Just wait until October comes around in Sleepy Hollow Courtesy: Eden, Janine and Jim/Flickr
Just wait until October comes around in Sleepy Hollow
Courtesy: Eden, Janine and Jim/Flickr

There are more than enough fall activities here in the weeks leading up to Halloween:


  • Haunted hayrides


  • Gothic mansions


  • Blazing pumpkins


  • Farmers markets


  • Live music


  • A5K run (that welcomes costumed runners)


  • A Halloween parade


And, of course, visits from the Headless Horseman!


More things to do near the Sleepy Hollow Street Fair

Keep an eye out for the annual Great Jack O’Lantern Blaze at Van Cortlandt Manor in nearby Croton-on-Hudson, NY, for a truly one-of-a-kind experience. This spectacular event features over 7,000 hand-carved, illuminated pumpkins and fall-themed treats.


Best of all, the village of Tarrytown, NY, and Sleepy Hollow are only a half hour drive away from Stanton House Inn. Fall is spectacular around here, I highly encourage taking advantage of it as much as possible.




Updated and Republished: October 2, 2023

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