Teddy Roosevelt
Theodore Roosevelt first visited Maine as a teenager in 1872, traveling by train to Dexter and then by stagecoach to Greenville to explore the Moosehead Lake region. It was a sickly, asthmatic boy who made that trip — his parents hoped, as later accounts note, that the crisp mountain air would do him good.

His connection to Island Falls specifically began a few years later, arranged through his Harvard tutor, Arthur Cutler, who had hunted with a well-known Maine guide named William Wingate “Bill” Sewall and thought the two would make a good match. In September 1878, young Roosevelt made his first trip to Island Falls, arriving with a cousin and two friends who had previously vacationed in the Mattawamkeag Lake region under Sewall’s guidance. The group traveled by train to Mattawamkeag Station, the nearest point reached by the railroad, then covered the remaining thirty-six miles an open, four-wheeled, horse-drawn carriage called a buckboard. That first night, they slept in a makeshift bed on the third floor of the Sewall family home.
The two men made an unlikely pair: a wealthy, asthmatic, bookish New Yorker and a towering, plainspoken Maine woodsman who neither drank nor smoked and read his Bible daily. A strong kinship quickly developed between the young man of wealth and social standing and the northern woodsman. Sewall, it turned out, was no simple backwoods stereotype. In addition to Sewall’s love of nature, he was well-versed in poetry, which helped sustain a friendship with a man of Roosevelt’s intellectual appetite.
Roosevelt returned to Island Falls again in February 1879. On that visit, Sewall and his nephew, Wilmot Dow, introduced Roosevelt to the world of logging camps. Roosevelt was captivated by the rhythms of life in the Maine woods — the log drives, the physical labor, the self-reliance the work demanded. He later recalled the simple pleasures of those trips: delicious nights spent under a lean-to by lake or stream in clear fall weather, or on balsam boughs in front of a blazing stump in winter.
The friendship proved durable and consequential. When Roosevelt headed west to the Dakota Territory in the 1880s to build a life as a rancher, he brought his Maine connections with him. Sewall and Dow accompanied Roosevelt, helping oversee operations at his ranch, and even chasing down thieves who tried to make off with Roosevelt’s boat. By the summer of 1886, with the ranching business battered by hard winters, summer droughts, and falling cattle prices, Sewall decided it was time to return home to Maine.
Even after Sewall’s Dakota years ended, the bond endured. The Sewall family was invited to Roosevelt’s presidential inauguration in 1901. The following year, passing through Bangor, Roosevelt made a point of tracking down his old friend. One day he called out from the balcony of the Bangor House that if anyone knew where Bill Sewall of Island Falls was, he wanted him to come in and have lunch right then. Sewall, startled, pushed through the crowd to much applause.
Late in his life, reflecting on what Maine had given him, Roosevelt wrote in a 1919 essay for the book My Maine, My State that he owed a personal debt to Maine because of his association with certain staunch friends in Aroostook County, Those friendships, he said, that had helped and benefited him throughout his life in more ways than one.
The physical traces of Roosevelt’s and Sewall’s friendship remain in Island Falls today. The William Sewall House on Crystal Road, built in 1865, still stands and was added to the National Register of Historic Places in 1982. Nearby, Bible Point — the 27-plus-acre point of land central to their outdoor excursions — was placed on the State Register of Historic Places in 1970 and carries a plaque installed by the Roosevelt Memorial Association in 1921, commemorating a friendship that shaped one of America’s most consequential presidents.
Sources
- Bangor Daily News, “Island Falls’ 150th celebration to highlight town’s close relationship with Theodore Roosevelt” — https://www.bangordailynews.com/2022/07/10/aroostook/island-falls-150th-anniversary-theodore-roosevelt-connection-joam40zk0w/
- Theodore Roosevelt Center, “Bill Sewall” — https://www.theodorerooseveltcenter.org/encyclopedia/dakota-and-ranching/bill-sewall/
- Bangor Daily News, “Like Roosevelt, visitors to Sewall House in Island Falls finding physical, emotional benefits” — https://www.bangordailynews.com/2014/01/16/living/like-roosevelt-visitors-to-sewall-house-in-island-falls-finding-physical-emotional-benefits/
- Maine Bureau of Parks and Lands, “History: Bible Point” — https://www.maine.gov/dacf/parks/discover_history_explore_nature/history/bible_point/history.shtml
- Wolf & Iron, “TRThursday: Bill Sewall – Roosevelt’s Manly Mentor” — https://wolfandiron.com/blogs/feedthewolf/trthursday-bill-sewall-roosevelts-manly-mentor
- Maine: An Encyclopedia, “Roosevelts in Maine” — https://maineanencyclopedia.com/roosevelts-in-maine/
- Wikipedia, “William Sewall House” — https://en.wikipedia.org/wiki/William_Sewall_House
