History & local legend
The former Winsor Inn on East High Street in Milford began as a summer house. Chef Harold Winsor converted it into an inn in 1926, and the building was also known for its years as the Judge School.
Its ghost stories evoke the children who once used the property. In a February 2012 Connections magazine account, visitors and townspeople described hearing footsteps and children laughing when no children could be seen. The voices became associated with the building’s school years, surviving in local memory after its classrooms and guest rooms had fallen quiet.
Sources
- Allison Mowatt, Connections, February 2012, printed p. 7, sidebar on the Winsor building and children’s footsteps and laughter
- National Register, Milford Historic District boundary increase, Winsor Inn, resource 194 and photograph 23
- Dated July 2024 street photograph identifying former Winsor Hotel and Judge School at 110 East High Street
- Esri World Geocoder, 110 East High Street, checked against the gabled mansion in the documentary photograph
