By Andy  O’Brien

        If you have a few hours to spare in Portland, the self-guided Freedom Trail tour will take you to several historic landmarks that tell the history of Portland’s Black community as well as the Underground Railroad, a secret network of anti-slavery men and women who helped enslaved workers escape to freedom in the northern states and Canada before slavery was abolished by the

        In the late 1700s and early 1800s, thousands of enslaved people escaped from the South to Northern “free states” where slavery had already been abolished. Fleeing slavery was extremely risky, as enslavers were legally allowed to pursue runaway slaves and force them back to the South. Article IV, Section II of the U.S. Constitution, signed in 1787, actually required the federal government to arrest runaway slaves. In 1793, Congress passed another law designating escaped slaves as “fugitives from justice” and authorized local governments to arrest and return them to their owners, while imposing penalties on anyone who aided their flight. 

        However, as the abolitionist movement gained strength, Northerners increasingly defied fugitive slave laws and refused to help Southern slaveholders catch escaped former slaves. Then in 1850, Congress passed the Fugitive Slave Act, which forced Northern citizens to aid in the capture of runaways, denied enslaved people the right to a jury trial, and increased the penalty for anyone interfering in their capture to a $1,000 fine and six months in jail.  

        As a result, Northern states were no longer safe for runaway slaves and they began fleeing to Canada, often with the help of free Blacks and sympathetic whites. On the Underground Railroad, participants used coded rail terms to avoid detection, such as  “conductor,” the person who transported fleeing slaves; “station,” a safe house; and “station master,” the owner of a safe house. Early 20th-century historian Wilbur Siebert noted that abolitionists in Boston formed a special “Vigilance Committee” to manage Black refugees from the South and sent some to Portland, where conductors helped them escape by steamship to Canada. 

        Formerly enslaved people also stowed away or arrived as paying passengers on merchant sailing vessels to Maine from Southern ports. Often they had help from a friendly Black sailor, according to Siebert. 

        Harriet Price and Gerald Talbot write in their book Maine’s Visible Black History that Portland’s Black community helped former slaves escape west by land on one of two routes around Sebago Lake to Bridgeton, through Parsonsfield, then on to New Hampshire and Vermont, and finally Québec.  

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The first stop on the Portland Freedom Trail is the Franklin Street Wharf where the Albion Cooper – a ship carrying lumber from Savannah, Georgia – arrived in 1857. Before coming into port, the captain learned that an escapedslave was onboard. Instead of reporting him to the authorities, the captain, named Smith, informed a group of local abolitionists and they formed a posse of Black and white anti-slavery men to board the ship in the evening to rescue the stowaway. The man was taken to a safe house at the “head of Hancock Street” where he hid until he could proceed to Canada the next day. 

        At 211 Newbury Street is a Freedom Trail marker for the home of Charles Frederick Eastman, who was a secondhand clothing dealer, mariner, hack driver, taxidermist, principal of the Abyssinian Meeting House school for Black children, minister, and conductor on the Underground Railroad. According to Eastman’s 1889 obituary, “no man did more for the poor fugitive [slave] than he.” 

        On the corner of Temple and Federal Streets is the Freedom Trail marker for what was once the hack stand of Black abolitionist Reuben Ruby (1798-1878). Ruby operated a coach (or “hack”) service in front of what was once the Elm Tavern and is said to have helped transport escaped slaves. 

        Other stops on the Freedom Trail include barber shops and secondhand clothing stores. Hack drivers like Ruby would take escaped slaves to pick up clothes, wigs, and fake beards to disguise themselves. Also on the trail are abolitionist churches like the Abyssinian Meeting House/Church, the historically Black church where the Rev. Amos Noe Freeman (1810-93) delivered incendiary anti-slavery sermons in the 1840s and 50s, as well as the Friends (Quaker) Meeting House, where activist William Lloyd Garrison helped launch the Maine anti-slavery movement in 1832. The Meeting House also was where rioting anti-abolitionist mobs smashed out windows and attacked abolitionists in 1836 and 1847.  

  A map of the Portland Freedom Trail is at   

Next month, we will tell the stories of some of the Underground Railroad passengers who fled the South, via the Underground Railroad through Maine.