History of Roosevelt Trail
by Kay Soldier

The major highway through Windham is known as Route 302 or the Roosevelt Trail.

According to a spokesperson from the Maine Department of Transportation, there has been a “road layout” on this location as far back as 1784, though not the same as today, probably from Raymond town line, along the Ward Road to Windham Center Road, and then to where Route 302 intersects today.

The Theodore Roosevelt Highway, as it was named, has seen many changes in its 200 year history. One of the most significant began in 1847 when that section of the road that begins at Ward Road was added. Cutting through some of the most fertile farmland in the Town of Windham, this alteration also took much of the traffic off the Windham Center Road. When completed, the addition went from the Ward Road to the intersection of Windham Center Road where it exits onto Route 302 today.

Other alterations were made in 1803, 1854, and in this century, the stretch from Albion Road to Nash Road was moved. Other alterations were made later; remnants of the “Old 302” can be seen at Foster's Corner (also known as the Rotary) at the intersection of Routes 202 and 302; and in North Windham, and further north in other towns like Raymond, Naples, and Bridgton.

In the Summer of 1995, a widening of the Road in North Windham, and alterations of traffic patterns by road markings and signs, made that area more safe for the travelers and residents.