This marker at Mariner’s Church on Fore Street highlights the property’s role in the Underground Railroad. The basement of the building was the site of an anti-slavery bookstore and print shop run by Daniel Colesworthy. Michael Kelley / The Forecaster

PORTLAND — The Portland Freedom Trail chronicles many of the city’s stops of the Underground Railroad, but Portland’s ties to the slave trade in the 18th and 19th centuries are much less documented, two historians said last week.

The former site of Reuben Ruby’s hackstand at the corner of Temple and Federal streets was an important site on the Underground Railroad. Ruby donated land for the Abyssinian Church and helped to start the first Black newspaper in the country. Michael Kelley / The Forecaster

“New England was at the very center of the slave trade and the region owes its (economic vitality) in the 18th and 19th century to the enslavement of Africans,” Meadow Dibble, director of the Atlantic Black Box Project, said during a virtual walking tour of the Old Port.

Atlantic Black Box is a public history project focused both on New England’s role in the slave trade and on the area’s Indigenous and African-American communities. The virtual tour last week was part of Maine College of Art’s Resilience Week.

Dibble said the nation cannot begin to solve the “racism that plagues society until we have collaborative work to uncover New England’s deeply suppressed racial history.”

In the late 1780s, cargoes of sugar and molasses coming into and out of Portland Harbor helped fuel enslavement in the West Indies, according to Seth Goldstein, an adjunct instructor in the Maine College of Art’s academic department and a marine historian who led the virtual tour.

Portland played a role in what was called the Triangle Trade. People were shipped from Africa to the West Indies in the Caribbean to be slaves on sugar and molasses plantations. That sugar and molasses was shipped to Maine and other parts of the United States where it was turned into rum, which, in turn, was then shipped to Africa and traded for more slaves.


While the importation of slaves was outlawed in this country in 1808, the trade remained legal in the Caribbean until much later and in Cuba until 1886.

Goldstein said in 1787, 73 of the 89 ships that departed Portland harbor were bound for the Caribbean. Following the repeal of the 1824 molasses tax, it was cheaper to make rum in Portland than it was in the Caribbean, he said. Portland supported seven rum distilleries and shipped out lumber, bricks and ice for the plantations in exchange for sugar, molasses and tropical fruit.

Matanza, a coastal community in Cuba, was built almost entirely from lumber from Maine, and cod caught off Maine waters was a key food source for the enslaved workforce, Goldstein said.

John Bundy Brown, a prominent businessman and real estate holder in Portland, gained much from of his wealth from the molasses industry, establishing in the 1840s the Portland Sugar Company that refined sugar from molasses shipped from the Caribbean. The refinery, located at Commercial and Maple streets, was one of only a few in the country and the largest building on the Portland waterfront. By the 1850s, it employed 1,000 workers. The building was destroyed in the Great Fire of 1866. It was rebuilt, but never found its pre-fire success.

Brown also built the former Falmouth Hotel, at 212 Middle St., and The Bramhall, a large estate near Vaughan Street in the West End, among other buildings. He sold some of the hundreds of acres of West End land he owned to rich friends who constructed large homes of their own.

“It is important for us to remember many of these buildings were built off the backs of enslaved African labor,” Goldstein said.


As Brown was starting his sugar refinery, Portland was becoming “an important stop on the Underground Railroad,” Goldstein said, especially after the enactment of the Fugitive Slave Act of 1850. Because the act dictated that slaves captured in northern states be returned to their owners in the South, the runaways weren’t truly safe until they crossed into Canada.

From Portland, runaway slaves either followed the Underground Railroad along the coast or through the Sebago Lake region.

The self-guided Portland Freedom Trail was established in 2007 to highlight some of the important sites in the city’s Underground Railroad efforts. One of those sites is 44 Exchange St., which in the mid-1800s was the site of Lloyd Scott’s secondhand clothing store. Goldstein said it was not uncommon at the time for places like clothing stores and barber shops, such as the one operated by Jacob Dickson at 243 Fore St., to be stops on the path to freedom.

“If you could change your physical appearance and not be captured, you would be free for the rest of your life,” he said.

Other stops included The Friends of Quaker Meeting House near the present site of Lincoln Park, the Mariner’s Church on Fore Street, First Parish Unitarian Universalist Church on Congress Street and the Abyssinian Church on Newbury Street, as well as private residences along India Street. Reuben Ruby’s hackstand at Federal and Temple streets also played a key role because Ruby could transport slaves.

Ruby was “Portland’s foremost African-American anti-slavery activist” and provided the land for the Abyssinian Church, which after being constructed in 1829, served as a social, religious and education center for the local African-American community until 1917. The building is in the midst of being restored and the Committee to Restore the Abyssinian recently secured $375,000 for the work.

“People have the misconception that abolishment and the Underground Railroad was driven by white allies, but it was really a Black movement,” Goldstein said.

Rep. Rachel Talbot Ross is working legislature that would require the teaching of African-American history in Maine schools. A similar effort in the last legislative session fell short.

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