Can you walk from Sleepy Hollow to Tarrytown? By Henry John Steiner On January 20, 2020 Yes. You can walk from Sleepy Hollow to Tarrytown pretty easily. The village main streets are only about a half-mile apart. Please follow and like us: Related Previous How far is Sleepy Hollow from Tarrytown? Next Is Sleepy Hollow Real? Comment on this FAQ Cancel replyYour email address will not be published. Required fields are marked *Comment Name * Email * Website Save my name, email, and website in this browser for the next time I comment. Notify me of new posts by email.