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Sleepy Hollow News

Sleepy’s Wide-Awake Street Fair–2023 Edition

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October 17, 2023

By Barrett Seaman–

Postponing the annual Sleepy Hollow Street Fair by a day because of the lousy weather reports turned out to be a winning bet. Though overcast and nippy, Sunday, October 15 was welcoming enough that several thousand people—many from someplace other than Sleepy Hollow—were drawn to Beekman Avenue. Three blocks of the village’s main thoroughfare were closed to vehicles but open to visitors of all ages from all over—and their dogs.

Work for The Hud Indy

According to the Chamber of Commerce, which runs the fair, there were 175 vendors arrayed along Beekman, many under white tents that turned out to be unnecessary.

Kids don’t look the slightest bit frightened

Not surprisingly, Latin dishes were dominant, but there were pizza and burger vendors as well—and of course Jimmy’s Soft Serve, parked strategically near the inflated bouncy castle and slides.

Inflatable slides, a bouncy castle and (though unseen here) Jimmy’s Soft Serve truck

There was live music, faux monsters, a haunted dollhouse, pottery and jewelry makers, a palm reader and J.P. Doyle’s doing a brisk business right in the center of things.

Some dolls!

Dogs were welcome, and the came in droves (or so it seemed). It’s a wonder there were no fights (well, maybe a few skirmishes), though one could speculate that the allure of so much savory food so close at hand served as a distraction.

Next stop: Halloween

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