The George Middleton House at 5 Pinckney Street, nestled in Boston's historic Beacon Hill neighborhood, holds a unique place in the city's history. Constructed in 1786-1787, it stands as a testament to both its architectural heritage and the African American community that played a pivotal role in shaping Boston's cultural and civic life during the late 18th century.

George Middleton, in partnership with Louis Glapion, oversaw the construction of this two-family residence. The house, now the oldest extant dwelling on Beacon Hill, represents a quintessential example of late 1700s Boston homes built by African Americans. Louis Glapion, a hairdresser who may have hailed from the French West Indies, resided at 5 Pinckney Street and operated his business there until his passing in 1813. His wife, Lucy, continued to live in the house until 1832.

During the American Revolutionary War, George Middleton took on a significant role as the leader of a Black militia company known as the Bucks of America. Although limited records about this group remain, it's believed that they safeguarded the properties of Boston merchants during the Revolution, possibly under the moniker "Protectors." Toward the war's end, Governor John Hancock presented the Bucks of America with a company flag, a cherished artifact now held by the Massachusetts Historical Society.

George Middleton, known for his skills as a horse breaker and livery man, was deeply involved in various Black community organizations. He served as the third Grand Master of the African Lodge, later known as the Prince Hall Masons. Additionally, in 1796, Middleton played a pivotal role in founding the African Society, also known as the Boston African Benevolent Society. This charitable organization was dedicated to community service, education, and the betterment of the African American community.

George Middleton married Elsey Marsh in 1781 at Trinity Church, and his legacy as a leader concerned with education, the abolition of slavery, and the welfare of his community left an indelible mark on Beacon Hill's history.

The George Middleton House is a treasured part of the Beacon Hill Historic District, which was rightfully recognized and listed on the National Register of Historic Places on October 15, 1966. This prestigious honor acknowledges the neighborhood's exceptional historical and architectural significance. The reference number for this historic district is 66000130.

While the house is privately owned today, visitors can appreciate its historical and architectural significance from the street. Parking in Beacon Hill is a challenge due to its primarily residential nature. Limited free parking is available along Hancock Street from 8 am to 6 pm daily, but spaces tend to fill up quickly. To ensure convenient parking, it is advisable to use the Boston Common Garage.