Sleepy Hollow and Tarrytown, NY FAQ’s: Click on each category title to see a list of questions and expand for answers. If you have more questions, click here to email me.

Tarrytown, NY General (3)

There is visitor information available from the chamber of commerce near Route 9 and Main Street.

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Washington Irving joked that the name “Tarrytown” comes from the tendency of colonial farmers to tarry at the tavern on market days.  In the “The Legend of Sleepy Hollow” the school teacher, Ichabod Crane, encounters the Headless Horseman near the Captors’ Monument at Patriots’ Park.  The Village of Sleepy Hollow is named for the Valley of Sleepy Hollow—the Valley of the Pocantico River as it runs through the Village of Sleepy Hollow.

main street tarrytown_winter
Main Street Tarrytown. Winter Snow

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Tarrytown and Sleepy Hollow are north of New York City but residents of the community do not generally think of themselves as living “upstate.” 

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