Whittlesey is a census-designated place in the town of Chelsea, Taylor County, Wisconsin, United States. Its population was 105 as of the 2010 census. The community of Whittlesey was started in the 1870s when the Wisconsin Central Railroad Company built its line up through the forests, heading for Ashland. The railroad placed a station seven miles north …Whittlesey is a census-designated place in the town of Chelsea, Taylor County, Wisconsin, United States. Its population was 105 as of the 2010 census. The community of Whittlesey was started in the 1870s when the Wisconsin Central Railroad Company built its line up through the forests, heading for Ashland. The railroad placed a station seven miles north of Medford where the line touched the Little Black River. It named the station Whittlesey, probably for Asaph Whittlesey, an early state legislator from Ashland, or possibly for geologist Charles Whittlesey who surveyed the area.