History of Windham, Maine in Timeline

By Popular Timelines Editorial Team · Updated: August 16, 2025

Windham, Maine, located in Cumberland County, is a town with a population of 18,434 as of the 2020 census. It encompasses the villages of South Windham and North Windham and is part of the Portland-South Portland-Biddeford metropolitan area.

April 4, 1919: Legislature passes act creating the Reformatory for Men

On April 4, 1919, the legislature passed an act creating the Reformatory for Men at South Windham. This facility is now known as the Maine Correctional Center.

1919: Designation of the transcontinental Roosevelt Trail

In 1919, the transcontinental Roosevelt Trail was designated, which encouraged more automobile tourists to drive through North Windham. Boody's store was built at the intersection of the Roosevelt Trail and Maine State Route 115 to sell goods.

1935: Identification as United States Route 302

In 1935, the transcontinental Roosevelt Trail was identified as United States Route 302, which encouraged increasing numbers of automobile tourists to drive through North Windham.