How a coastal Maine town almost became part of Canada

CBC

23-06-2025

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When U.S. President Donald Trump started talking about annexing Canada to make it the 51st state, people in Castine, Maine, took notice.
The town, after all, was twice occupied by Great Britain two centuries ago.
The British wanted to carve out a new colony that would be part of British North America — in effect doing the opposite of what Trump has been musing about.
"When I do walking tours, I jokingly tell people that this could have been Canada very easily," said Lisa Lutts, the recently retired executive director of the Castine Historical Society.
"If the War of 1812, if the Treaty of Paris had been different, this would have been Canada. And I always joke and say, well, I would have had better health care. That's my joke, and people love it."
Castine's history of occupation is visible in the historical markers and remnants of British forts that dot its small grid of streets overlooking Penobscot Bay.
Kamala Harris beat Donald Trump here by 47 percentage points in the presidential election last fall, and the president's aggressive comments about Canada were deeply unpopular in Castine and nearby coastal communities.
"This isn't how you treat your allies," said Pete O'Brien, a resident of nearby Rockland who was showing relatives from California the earthworks of Fort George, built by British troops in 1779.
"We're about as close as it gets to you politically, culturally, geographically."
Liam Riordan, a historian at the University of Maine at Orono and an expert on the revolutionary period, said Trump's rhetoric represents "a failure to understand the close ties and close relationships that we share."
"I think in Maine, the reaction to that has really been one of being appalled and embarrassed."
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Castine's elevated geographical location at the tip of a peninsula on the eastern side of Penobscot Bay made it a strategic location for colonial powers fighting over North America.
A newspaper correspondent referred to its capture in 1814 as "perhaps one of the most admirable military positions in the world."
In the 1600s, present-day Castine was the western edge of the French colony of Acadia, with the British-held Massachusetts Bay Colony on the other side of the bay.
France gave up all its North American territory in 1763, but when it backed the rebels in the American Revolution, the British seized Castine in case the French decided to take it back.
A revolutionary fleet sailed to Castine to push out the British but failed miserably.
"A lot of Americans have no idea about the Penobscot expedition and the battle that took place here, because we lost," Lutts said. "We remember the ones that we won."
When the revolution ended and the British recognized U.S. independence, "any reasonable person during the treaty negotiations … would have said almost certainly the Penobscot River would be the border," Riordan said.
But John Adams, one of the negotiators, pushed for the St. Croix River to be the border because he recognized how Castine would give the Americans better access to lucrative fish stocks and trade routes.
Four hundred loyalists who had come to Castine during the Revolution to remain under the British Crown moved again, this time settling what would become Saint Andrews, N.B.
Several even moved their houses there on boats and placed them on a street grid similar to Castine's, the reason the two towns resemble each other.
Three decades later, during the War of 1812, the British returned to capture Castine again.
The story goes that American troops at Fort Madison knew they were outnumbered, fired one perfunctory cannon shot for honour's sake and quickly fled.
A local pastor, William Mason, grabbed a white table cloth from his dining room and headed down to the harbour to wave it as a signal of surrender.
Castine was a boomtown under British occupation thanks to trade with other British ports such as Halifax and Saint John.
"Business is brisk and speculators are daily flocking in from every quarter," the Hartford Courant reported in November 1814. "The war, or rather peace, with the British is becoming very popular here."
But the treaty that ended the War of 1812 returned Castine to the U.S. again.
Thousands of pounds collected by the British customs house in Castine remained with the British and was used by Nova Scotia's governor, Lord Dalhousie, to establish a college that later became Dalhousie University.
"Another reason why we feel very close to Canada is that our money is up there at that university," Lutts joked.
"They're not letting us in for free though. They should let Castiners in for free, don't you think?"
The end of that war also marked the end of Castine changing hands, but the town's history remains a touchstone for residents to this day.
"We understand ourselves by thinking about our relationship with the past," Riordan said. "And Castine really leans into this more than many other local towns."
Some local residents aren't sure life would be that different here if history had taken a different turn.
"If the Canadian border had been here, I don't think a lot would have changed, because when I look at Maine, I see us as a borderland between Canada and the United States anyway," O'Brien said.
"I think there's also a lot of understanding and acceptance and appreciation of the Canadians down here as well. And so it would have just pushed all of that a little farther south, right?"