At the turn of the 18th century, the merchants and seafarers of Boston and surrounding communities petitioned for a "beacon" to be erected to indicate the entrance to Nantasket Roads. July 1715, the provincial government answered this call by passing legislation to establish a lighthouse. Little Brewster Island, owned by the Town of Hull, was ascertained to be the most appropriate location. In August 1715, Hull transferred the property to the Province of Massachusetts.

The lighthouse station completed in 1716 had 60 foot tower constructed of granite rubble stone, a wood framed keeper's house, a barn, and a wharf. The lantern lit on 14 September by Keeper George Worthylake, illuminated with ordinary household candles or possibly oil lamps. A tragedy occurred when Worthylake, his wife Ann, daughter Ruth, slave/servant Shadwell, and friend John Edge, drowned. They were in a row boat, approaching the island, when it unexpectedly capsized. All five lives were lost. On the pier were their daughter, Ann, and a friend, Mary Thompson, witnessing the misfortune.

Robert Saunders was temporarily assigned to the light until the slated appointed keeper, John Hayes, became available. Saunders was on duty for only a few days when he was also drowned. Keeper Hayes was on duty by November 18, 1718. It was customary in this era for ships to fire black powder from a large gun or cannon when navigating through fog when they suspected other vessels to be nearby. After the cannon was fired, they would wait for a reply. The loudness of the sound would be an indicator as to how close or faraway the vessels were to each other to determine if any actions needed to be taken to avoid collision. Keeper Hayes had no means to answer vessels in the fog to warn them of their proximity to the island and nearby ledges. He requested from the provincial government a "great gun" to answer ships in the fog. It was approved and a cannon sent to the island in 1719, thus Boston Light became a fog signal station as well as a light station. Today, the cannon is the oldest Coast Guard artifact in the country and is displayed at the museum room at the base of the lighthouse tower at Little Brewster Island.

At the conclusion of the Revolutionary War, the tower was promptly reconstructed by the Commonwealth of Massachusetts and relit on December 5, 1783 by Thomas Knox. The newly established U.S. government received custody of Little Brewster Island and Boston Light on June 10, 1790.

Over the next 232 years, the tower was refurbished numerous times. Technological improvements through the centuries brought forth various modifications and changes to the lighting apparatuses and fog sound signal devices. In 1859, a duplex house was constructed for the keeper, an assistant keeper, and their families. Also, the tower was raised to 89 feet to accommodate the 11 foot second order Fresnel lens with its rotating clockwork machinery. On December 20, 1859, the lens cast its powerful beams across Massachusetts Bay for the first time.

Management of the Lighthouse Service changed in 1939 when it was absorbed into the U.S. Coast Guard. Maurice Babcock (1927-1941) became the last civilian Lighthouse Service keeper at Boston Light and Ralph Norwood the first Coast Guard Keeper as a first class petty officer. The significance of this administrative shift became apparent in 1958 when preparations were made for Boston Light to transition to a "stag" - all male - station. By 1960, wives and children had been relocated to the mainland. In 2003, the position reverted to a Coast Guard civilian position, precipitated by the state of the nation in the wake of September 11, 2001 terrorists attacks. Light Station Boston is manned with a civilian keeper and a cadre of Coast Guard Auxiliary volunteers. Over the past 300 years, 70 documented principle keepers have been appointed since the station was established in 1716.