Whittlesey is a census-designated place in the town of Chelsea, Taylor County, Wisconsin, United States.

[1] 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.

[7] A 1913 map shows a "depot", post office, and blacksmith shop facing the railroad, with the school on the southeast side of town.

[9] As of 2023 Whittlesey is a quiet cluster of homes scattered among the trees a short drive north of Medford, with the Pine Line bike trail passing through on the old railroad right-of-way.