26 Court Street stands on land that is part of the traditional homelands of the Massachusett Tribe. Located along the main trail into and out of Shawmut (the place we now call Boston) and the small cove facing Boston Harbor, this place was ideal for habitation. In spring, the Massachusett people would return to the coast and islands to re-occupy their wetus (traditional dome-shaped homes), plant their corn fields, and collect clams from the nearby mudflats. After the fall harvest, they would return to their winter homes near the protective Blue Hills to avoid the harshest conditions along the stormy coast.

The first recorded history of 26 Court Street can be found in the court records of Boston in 1632. On October 3 of that year, the selectmen ordered the construction of a "howse of correcc̅o̅n." Those orders were not quickly followed. In September 1634, William Brenton was tasked with overseeing the prison's construction. When it opened in late 1635, it was the only formal prison in the Massachusetts colony.

Brenton's professions included merchant, investor, and later the governor of Rhode Island. He also seems to have gained a reputation for successful jail construction. In August 1638, Brenton was given oversight of building a 10'x12' prison in Portsmouth, New Hampshire.

Richard Bracket was the first named keeper of Boston's prison. His role was to maintain the building, yard, and prisoners held inside. An order to also make the jail both warm and safe did not come until 1641. By 1683, the prison had been rebuilt using stone.

There were many ways to find oneself in prison in 1600s Boston. Early imprisonable crimes included being unable to pay debt, missing church, being an outspoken woman, and calling the Boston church a "whore." Perhaps the most notorious 17th-century prisoners at the Boston jail included the accused witches of Salem. Most of the accused passed through the prison as trials and examinations brought the accused between Salem and confinement in various towns nearby.

The first three women falsely accused of witchcraft in February 1692 were held in the Boston jail: Sarah Good, Sarah Osborn, and Tituba. A month after Sarah Good's arrest, her 4-year-old daughter, Dorothy "Dorcas" Good, was accused of witchcraft and in jail. Sarah was pregnant and was forced to give birth to a baby girl while incarcerated. Over the eight months Dorcas was imprisoned before her release, she witnessed both the death of her infant sister and the removal of her convicted mother for execution. Sarah Osborn died in prison, the first victim of the Salem Witch Trials, and three other accused witches shared her fate in the prison.

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Conditions in the prison were horrendous. One prisoner stated "If there is any such thing as a hell upon earth, I think this place is the nearest resemblance of any I can conceive of," with the prisoners supplied a single pillow and blanket, and no glass on the barred windows preventing cold and weather from entering the cells. A 1659 letter describes the conditions inside the cell of Mary Dyer during her third incarceration. Dyer was imprisoned for being a Quaker, and spent her days wet from rain in a cold bare room with a dirt floor. Mary Dyer was hanged on Boston Common the following year.

The jail was rebuilt and expanded in 1704, but that structure would be short-lived. The massive 1711 fire that swept through the core of Boston and took out such structures as Boston's first town house (now the Old State House site) also destroyed the jail. The new building (Figure 1) would stand until 1797 when it was again replaced with a new structure. This structure, the 5th jail on the site of 26 Court Street, would remain until it was officially moved to Leverett street in 1822 and the building was demolished the following year.

In 1836, the new Suffolk County courthouse was built on the site (Figure 3). Standing throughout the remainder of the 19th century, it hosted some of the most important trials during Boston's abolitionist movement and the Fugitive Slave Act hearings. This 1850 act required the return of enslaved people to their enslavers if they were found in a so-called "free state." The courthouse became the scene of active rebellion against this act.

The most famous incident at the courthouse at 26 Court Street was later called the "Boston Slave Riot." This 1854 event revolved around Anthony Burns, a Black man enslaved in Virginia. He escaped to Boston, but his enslaver found him and he was arrested. Following a meeting of the Committee of Vigilance, an anti-Fugitave Slave Act group, at Faneuil Hall on May 26 1856, a group of at least 25 men armed with axes and revolvers stormed the court house. The jailbreak attempt was unsuccessful, however, and resulted in several arrests and the death of one jail guard.

President Franklin Pierce sent Marines to Boston following the riot. The citizens of Boston, riled up by the failed attempt to free Burns, awaited the final verdict. The judge, required to enforce federal law, favored the return of Anthony Burns to slavery.

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On June 2, 1854, over 250 armed Marines and pro-slavery civilians escorted Burns from the court house to T wharf off Long Wharf. They were confronted by an estimated 50,000 Bostonians who swarmed the route to the ship. While some Bostonians were there in support of Burns's return to slavery, the majority were there in protest. Skirmishes between protesters and the escorts resulted in several injuries. Many protested by using the symbolism of mourning the death of freedom. Homes along the route were decked in black funeral drapes. One home near the State House had a black coffin suspended from a window with the words "The funeral of liberty" written on it. Further down State Street, a rope was passed between buildings suspending an American Flag draped in morning clothes. Burns eventually reached the ship waiting for him and he was returned to enslavement in Virginia . He was later freed and returned to Boston after a group of abolitionists purchased his freedom from his enslaver.

In 1909, the court house was demolished after the court moved to its current location in Pemburton Square. In its place, the City of Boston created the City Hall annex, reusing the historic granite columns that once decorated the front of the former court house. That building is 26 Court Street, the new home of the Office of Historic Preservation.

The rehabilitation of 26 Court Street starts a new era for the historic building. Over the years, many city departments, including the Boston Public Schools, have made 26 Court Street their home. Starting in 2026 the building will house the Mayor's Office of Housing, Public Facilities Department, Office of Economic Opportunity and Inclusion, Office of Veterans' Services, Environment Department, Office of Climate Resiliency, Mayor's Office of Arts and Culture and the Mayor's Office of Food Justice.

The rehabilitation of 26 Court Street has preserved historic architectural details while integrating modern technologies. The building is fully accessible for all employees and visitors. The building is highly energy efficient and fossil fuel-free, relying on all-electric heating and cooling systems.  The ground floor of the building has many meeting rooms providing comfortable and functional spaces to service the public and foster public engagement. The third floor is designed to bring city departments together with its intentionally designed collaboration space.

There are also dedicated parking spaces with charging stations for city vehicles on City Hall Avenue adjacent to the building.

The rehabilitation of 26 Court Street proves that historic buildings can be modern, energy-efficient, and retain their historic character-defining features.

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