An early photo of Route 302 in Windham. In 1915, the Stanley Hotel was a popular place to stay. Contributed / Windham Historical Society

I have often wondered why Route 302 is also called Roosevelt Trail. I assumed it was because the road was built during President Franklin Delano Roosevelt’s New Deal as part of the Works Progress Administration that supplied paying jobs to unemployed people during the Great Depression. I was wrong.

The road’s beginnings go back to 1784 when it served as a stagecoach road that went from Bridgton to Portland. At that time, it was called Bridgton Road and it traveled through the center of Windham up Windham Hill and then down Windham Center Road. It was not unusual at the time to see draft horses pulling heavy loads along the roadway.

Haley Pal, a Windham resident and active member of the Windham Historical Society, can be contacted at

In 1858, the road took a new direction when a connection was built that ran between the intersection of Windham Center and Ward roads and the present Route 302. This was called New Anthoine Road and it became popular for helping travelers avoid the challenges of climbing Windham Hill.

But where does the Roosevelt connection come in? The road was actually named for President Theodore Roosevelt. While he was president, Teddy Roosevelt was very much in favor of providing cross-country routes to Americans who were increasingly enjoying traveling in their new automobiles. One of the routes he proposed went from Portland, Maine, to Portland, Oregon. Upon his death in 1919, the president was honored when the Portland-to-Portland road was completed and named the Theodore Roosevelt International Highway. A portion of the 4,060-mile road went through Canada, thus the international designation. Over time, the road name has changed. From 1922 to 1935, it was part of the New England Road Marking System known as Route 18. It was redesignated as Route 302 in 1936.

It does seem fitting that a Maine road pay tribute to the Roosevelt name. Teddy had a long relationship with our state. His first visit was in 1872 at the age of 14 when he traveled by train to Dexter and then took a stagecoach to Greenville to visit the Moosehead Lake region. In 1878, he returned to explore what is now Katahdin Woods and Waterways National Monument. He made three trips that year and was shown the sights by Maine guide William Wingate “Bill” Sewall of Island Falls, who went on to be a longtime friend who later ran Roosevelt’s Elkhorn Ranch in the Badlands of North Dakota.

A snapshot of Route 302 in Windham in 1940. Contributed / Windham Historical Society

In the summer of 1880, Teddy made another trip to Maine when he stayed with a college friend at Schooner Head in Bar Harbor and they discovered the beauty of what is now Acadia National Park together. In 1902, he paid a visit to James G. Blaine while touring the state and in 1914, Roosevelt rode on the new Portland-Lewiston Interurban Line Electric Railway where he was greeted by enthusiastic crowds all along his way. He paid another visit in 1916 during his final presidential run and made his last trip to Maine in 1918 when he and his wife spent two weeks in Islesboro after their son was killed in WWI.

FDR also had a fondness for Maine because it was his last stop before crossing over the border to his beloved home on Campobello Island in Passamaquoddy Bay just over the border in Canada. He spent the summers of his childhood there and it was a welcome retreat from the pressures of the presidency in his later years. The family would sometimes make a stop in Lubec to pick up supplies for their vacation.

In June of 1941, Eleanor Roosevelt wrote about a day she spent while staying in Maine. “Yesterday morning, on the water, it was cool and we had a grand breeze on our way over to Eastport. Once landed there, we visited various old friends in the fruit store, the drug store and the bank. Then we took a taxi to Quoddy Village to visit the National Youth Administration. I was impressed by the excellence of the workshops and the tremendous interest the boys show in the work they are doing.” She made another Maine visit two years later when she addressed working women in Portland and South Portland and commended them for living up to the challenges of running a home and working at the same time.

So, there is a connection between the Roosevelts and Maine, and I’m glad we continue to refer to Route 302 as Roosevelt Trail in Windham. The nomenclature mystery may have ended, but it’s nice to see the name live on.

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