A committee headed by Lieutenant Governor William Tailer planned for the lighthouse. After visiting several of the harbor islands and conferring with the area's most experienced shipmasters, Tailer reported that the best site for the lighthouse was "the Southernmost Part of the Great Brewster called Beacon Island." Beacon Island, now known as Little Brewster, is attached to Great Brewster by a sand bar.

On July 23, 1715, the General Court of Massachusetts passed the Boston Light Bill. It read, in part:

Whereas the want of a lighthouse erected at the entrance to the harbor of Boston hath been a great discouragement to navigation by the loss of the lives and estates of several of his majesty's subjects; for prevention thereof -- Be it enacted...that there be a lighthouse erected at the charge of the Province, on the southernmost part of the Great Brewster, called Beacon Island, to be kept lighted from sun setting to sun rising.

The first lighthouse was financed by a tax of a penny a ton on all vessels coming into the harbor, and the same amount for vessels leaving the harbor. Smaller coasting vessels paid only two shillings as they left the harbor. Fishing vessels and small vessels transporting lumber and other building materials locally were taxed five shillings yearly. The exact dimensions of the original stone tower aren't known, but it's believed it was at least 50 feet tall. The first keeper, 43-year-old George Worthylake, lighted the lighthouse on Friday, September 14, 1716.

On November 3, 1718, Worthylake went to Boston to collect his pay. On his way back he stopped at Lovell's Island, where he and his wife and their daughter Ruth boarded a sloop heading for Boston Light. A friend, John Edge, accompanied them. The sloop anchored near Little Brewster Island a few minutes past noon, and Shadwell paddled out in a canoe to transfer the party to the island. Young Ann Worthylake and a friend, Mary Thompson, watched from shore.

Suddenly, the two girls on shore saw "Worthylake, his wife & others swimming or floating on the water, with their boat Oversett." The canoe had capsized, and all five people drowned. George, Ann, and Ruth Worthylake were buried beneath a triple headstone in Copp's Hill Burying Ground in Boston's North End.

Benjamin Franklin, 12 years old at the time, was urged by his brother to write a poem based on the disaster. Young Franklin wrote a poem called The Lighthouse Tragedy and hawked copies on the streets of Boston. He referred to it years later as "wretched stuff." Not one copy existed until 1940, when Maurice Babcock, Jr., son of Boston Light's keeper, found a tattered copy in the ruins of an old house on Middle Brewster Island, near Little Brewster. The copy could not be proved to be authentic so no value could be placed on it.

Robert Saunders, a former sloop captain, became Boston Light's second keeper on a temporary basis, until a new permanent keeper could be chosen. Saunders apparently drowned only a few days after taking the job; no details of the incident survive.

John Hayes, an experienced seaman described as an "able-bodied and discreet person," became the next keeper. Hayes asked for a gallery to be installed around the tower's lantern room so that he could clean the glass of ice and snow. Hayes also noted the need for some kind of fog signal, asking that "a great Gun may be placed on the Said Island to answer Ships in a Fogg."

A cannon, America's first fog signal, was placed on the island in 1719. It served for well over a century. After some years at the Coast Guard Academy in New London, Connecticut, the cannon was returned by helicopter to its rightful home in 1993. Today the venerable fog cannon sits on a new carriage in the base of the lighthouse tower.

John Hayes retired because of advancing age in 1733. Robert Ball, an Englishman whose stay of about 40 years would be the longest stint of any keeper in the station's history, succeeded him. Ball was assisted by a slave known as Samson, who died in 1762 and was buried on Rainsford Island in the harbor.

A bad fire gutted the lighthouse in 1751, and for a time the light was shown from a 40-foot spar. The early lighthouse was struck by lightning on several occasions, including an instance in June 1754 when lightning "tore off shingles from several places on the outside." The installation of a lightning rod was delayed because of the objections of some "godly men" who thought it "vanity and irreligion for the arm of flesh to presume to avert the stroke of heaven," according to a 1789 article. Practicality eventually won out and a lightning conductor was installed.

In July 1775, Boston Harbor and the lighthouse were under the control of the British. On July 20, American troops under Maj. Joseph Vose landed at the lighthouse and took lamps, oil, and some gunpowder, and burned the wooden parts of the tower. After leaving the island they had to outrun an armed British schooner, and two Americans were wounded. An eyewitness described "the flames of the lighthouse ascending up to Heaven, like grateful incense, and the ships wasting their powder."

As the British worked to repair the tower, 300 American soldiers under Maj. Benjamin Tupper landed at the island on July 31. They easily defeated the British guard and again burned the lighthouse. As they tried to leave, they found their boats stranded; the tide had gone out. This gave British vessels time to reach the scene.

The Americans managed to launch their boats as the British fired on them. American troops at Nantasket in Hull helped by firing a cannon at the British boats, landing a direct hit on one. This turned the tide of battle and the Americans escaped with only one soldier killed. George Washington praised the "gallant and soldier-like behavior" of the men under Major Tupper.

At the end of their occupation of Boston Harbor during the Revolution, the British lingered in the harbor for some months. As they left the area on June 13, 1776, one of their final acts was to set off a timed charge on Little Brewster, completely destroying the lighthouse. The remains of the metal lantern were used to make ladles for American cannons.

It took until 1783 for Boston Light to be rebuilt. The new 75-foot rubblestone tower, built by the order of John Hancock, governor of Massachusetts, was designed "to be nearly of the same dimensions of the former lighthouse." It has sometimes been claimed that part of the original tower was incorporated into the new one, but there is no evidence to support this claim.

Thomas Knox was the first post-Revolution keeper. He stayed in the position for 27 years, also serving as a harbor pilot. The light station was ceded to the federal government in 1790.

In June 1809, the local lighthouse superintendent, Henry Dearborn, found three perpendicular cracks in the tower, extending for almost its entire height. Six iron hoops were added around the tower for extra support. One band was removed in the early twentieth century; five aluminum bands are in place today.

Winslow Lewis installed a new lantern in 1839, along with new 21-inch reflectors from England. The engineer I. W. P. Lewis, Winslow's nephew, visited Boston Light for his 1843 report to Congress. He was critical, calling the tower "loose and leaky," and noting that the wooden stairway was so rotten "as to be unsafe of ascent." The two-story house, with four rooms on each floor, was in good repair, as was a new boathouse.

A 1,375-pound fog bell, operated by clockwork machinery, replaced the old cannon in 1851. Moses Barrett, a Gloucester native, saw much change during his time as keeper (1856­62). The Lighthouse Board had suggested in 1857 that the tower be rebuilt at a cost of $71,000, but improvements were made instead.