Part of an occasional series answering readers’ questions about Maine. 

Q: Why is Route 302 called Roosevelt Trail?

Did Teddy ride his horse from Portland to Fryeburg? Did Franklin and Eleanor use it for a ride into the country?

You’re on the right track, or should we say, trail.

Both Theodore and Franklin Roosevelt had ties to the state. The name doesn’t come from any presidential trips through the Sebago Lake region, however.

Franklin Delano Roosevelt mostly passed through Maine to reach his beloved Campobello Island in Passamaquoddy Bay and just over the border in Canada. He spent summers there as a child and visited the island three times while president.

Theodore made some formative visits to Maine’s North Woods as a young man, as well as some later swings through southern Maine as president, and it’s the Rough Rider who gets credit for parts of Route 302 carrying the family name.

While president, Theodore Roosevelt proposed linking roads from east to west to provide cross-country routes for the growing number of automobiles in America. One of these was proposed to stretch from Portland, Maine, to Portland, Oregon.

After Roosevelt died in 1919, among the memorials to honor the 26th president was an effort to name one of the auto trails after him. The Portland-to-Portland route would become the Theodore Roosevelt International Highway. A portion of the 4,060-mile route goes through Canada, hence the international designation.

The highway network was completed in 1930, but by then the U.S. had adopted a numbering system, which was used to designate the roads that were part of the highway linking east and west. The roads are best known now by those numbers, including Route 302 in Maine and northern New England and Route 2 through much of upper Midwest and Rocky Mountain states.

While not its official name according to any state or federal law, some parts of the country still refer to the highways as Roosevelt’s roads. It’s not surprising that Maine is one of them.

Roosevelt had strong ties to Maine and about a year before he died, wrote about his trips to Aroostook County and hunting with William Sewall and Wilmot Dow. The letter was used as a foreword to the book “My Maine,” intended as a resource for Maine history courses in the state’s schools.

Twenty-one year-old Theodore Roosevelt, right, is shown during a visit to Maine in 1879 with his hunting companions, William Sewall, left, and Wilmot Dow. Maine Bureau of Parks and Lands

“I owe a personal debt to Maine because of my association with certain staunch friends in Aroostook County; an association that helped and benefited me throughout my life in more ways than one,” he wrote. “I was not a boy of any natural prowess and for that very reason the vigorous out-door life was just what I needed.”

According to the state Bureau of Parks and Land, on one trip to Mattawamkeag Lake, Roosevelt would take his Bible to read at a particular spot in the woods. The spot was named Bible Point and it’s now a state historic site.

In the letter, posted on the state agency’s website, Roosevelt reminisces about his hunting and fishing trips with Sewall and Dow, which began in the 1870s and included a month snowshoeing and a climb of Mount Katahdin.

“It was a matter of pride with me to keep up with my stalwart associates, and to shift for myself, and to treat with indifference whatever hardship or fatigue came our way. In their company I would have been ashamed to complain!” he wrote. “And I thoroughly enjoyed it. I was rather tired by some of the all-day tramps, especially in the deep snow, when my webbed racquets gave me “snowshoe feet”, or when we waded up the Munsungin in shallow water, dragging a dugout, until my ankles became raw from slipping on the smooth underwater stones; and I still remember with qualified joy the ascent and especially the descent of Katahdin in moccasins, worn because I had lost one of my heavy shoes in crossing a river at a riffle.”

Roosevelt reminisced that the two men, their wives and children visited him on his cattle ranch in South Dakota, where he retreated after his wife and mother both died on Valentine’s Day in 1884. Sewall’s and Dow’s wives – he provided no first names of the women – both gave birth while on the ranch, he wrote. The two newborns were referred to as “the Badlands babies,” said Philip Morse, a volunteer project manager at the the Seashore Trolley Museum in Kennebunkport.

Morse is helping with the effort to restore the Narcissus, a streetcar that ran between Portland and Lewiston from 1914 to 1933. Roosevelt rode on the streetcar – he called the trip “a bully ride,” Morse said – in 1914 while campaigning in Maine for progressive candidates.

That 1914 trip was one of 11 visits by Theodore Roosevelt to Maine that Morse has been able to document. In 1902, Roosevelt spent two days in the state, giving eight speeches nearly a year after he became president following the assassination of William McKinley. His last visit was during the summer of 1918, when he and his wife spent more than two weeks in Islesboro after their son was killed in World War I.

Morse said Roosevelt traveled widely through Maine during the four decades of his visits here. “There are pinpoints all over the state,” Morse said, adding that he’d like to see a Roosevelt Maine Heritage Trail developed so people could visit the sites where Roosevelt traveled.

And, he said, Bill Sewall became something of a father figure to Roosevelt after his father died in 1878.

Roosevelt, center, with Sewall and Dow in an undated photo. Maine Bureau of Parks and Lands

Roosevelt wrote in his letter that his Maine friends, the Sewalls and Dow’s widow, visited the White House sometime during his time in office, which ran from September 1901 to March 1909, and they apparently spent hours discussing current affairs.

“Never were there more welcome guests at the White House,” he wrote.

Meanwhile, 102 years after his death, the auto trail that Roosevelt envisioned still connects Maine to Oregon. The Roosevelt name is more common in the West. In Maine, Route 302 carries several different names as it winds through the cities and towns of Cumberland County.

Route 302 begins in Longfellow Square and is known as Forest Avenue in Portland, for instance, and Portland Road and Bridgton Road at various other points. But parts still bear the Roosevelt Trail name – primarily from Westbrook through Windham to Naples.

The Roosevelt Trail name doesn’t show up on any maps of Legislature-named roads in Maine, said Paul Merrill, spokesman for the Maine Department of Transportation.

In fact, he noted, Route 302 from Portland to the New Hampshire border is officially designated the 10th Mountain Division Highway, a name that the state Legislature approved in a 2001 law. The 10th Mountain Division was created before World War II as a unit dedicated to fighting in mountainous areas and winter conditions. In recent years, it has been active in Iraq and Afghanistan.

The 2001 law naming Route 302 specified that the new designation would not change any names that municipalities may have adopted for their sections of Route 302, leaving Roosevelt Trail intact as a lingering memorial to the president who said he owed a debt to Maine.