Is Sheboygan a popular destination for winter activities like sledding and tobogganing?Home / Sheboygan Q&A / Is Sheboygan a popular destination for winter activities like sledding and tobogganing? Sheboygan Q&A ByBrian Bateman August 18, 2023 ShareYes, Sheboygan is a popular destination for winter activities like sledding and tobogganing, with designated hills and slopes for winter fun.