The Historic Halfway Homestead is Windsor’s first historic landmark site. It comprises two historical buildings including the oldest structure in the town: The Halfway House. The Halfway House got its name for being halfway between Greeley and Laporte on the Overland Trail Cutoff Route, and was originally a stagecoach stop, post office, and pub. The other historic building on the site is the Dickey Farmhouse, completed in 1907. The Dickeys were a prominent Windsor Family who operated one of the largest farms in the region. The site is currently under development to become an agricultural heritage site with construction planned for 2023. The Historic Halfway Homestead is currently not open to the public except for special programs and events.