October 11th Cruise-in 12th is the show. Sleepy Hollow Cruisin' Classic is an Antique & Classic Car Show in conjunction of our annual Sleepy Hollow Craft Show. Free Entry. Registration all day Friday, October 11th. Awards on Saturday, October 12th. People's Choice, Popular Vote. Dash Plaques for first 100, food, music, arts & crafts vendors and kids activities! Contact: Switzerland County Tourism (812) 427-3237 for more information.