South Boston Early History

Like a good mystery novel, the history of South Boston is full of intriguing twists and turns. From bucolic bliss to nucleus of opportunity for land-starved Boston, the peninsula has withstood tumultuous change over the past 400 years. The following includes a few early highlights, based on a detailed account of the era that appears in the Thomas H. O’Conners book, South Boston, My Home Town (1994).

Pow-Wow Point to Pastureland

In 1635, accompanied by a hundred followers, 23 cows and heifers, three calves and eight mares, Reverend Richard Mather arrived at Dorchester, a Pilgrim settlement established in 1630. Dorchester was located on a peninsula known by the native inhabitants as Mattapan, south of present-day Boston.

Directly across the water from Dorchester was another peninsula so narrow that it was reduced to an island at high tide. It was the site of a fresh-water spring shaded by “a magnificent growth of weeping willows.” According to O’Connor’s account, records show that inhabitants from Dorchester first came ashore near the beach now located at the foot of K Street in South Boston.

The slender peninsula later became known as Dorchester Neck. Called Mattapannock by the natives, it was the location of “Pow-Wow Point,”  an important ceremonial meeting place, and possibly a burial ground too, for the region’s native population. Shortly before the arrival of the Pilgrims, these native peoples were decimated by a horrific plague.

Tory Stronghold to Rebel Fortification

In 1765, British Parliament passed the Stamp Act on the colonies of British America as a means of raising tax revenue. The act required outraged colonists to print publications and legal documents on paper carrying an embossed revenue stamp. Quantities of the despised stamped paper were stored at Castle William, the present-day site of Fort Independence on Castle Island in South Boston.

Following the Boston Massacre in 1770, the 14th and 29th British regiments withdrew from Boston to the safety of Castle William, and at the time of the Boston Tea Party in 1773, a group of loyalists sought refuge there. In 1775 the American rebels forced the British to evacuate Boston. As they made their retreat, the British set ablaze the fortifications, which were subsequently repaired by American troops under Lt. Colonel Paul Revere.

The date of the British evacuation, George Washington’s first victory of the war, is recognized as an official holiday in Boston and other parts of Suffolk County. Evacuation Day falls on March 17, coinciding with Saint Patrick’s Day. As if Southie didn’t have enough to celebrate that day!

South Boomtown in the Making

In 1803, a shrewd and well-connected group of Bostonians purchased a significant amount of property on Dorchester Neck. The following year the city of Boston annexed the entire 600-acre peninsula, at that time home to about 60 families.

The speculators busied themselves improving access to the area by building a toll bridge across the channel to the South End. They also set about planning the orderly street grid that remains to this day, with Dorchester Street running north-to-south and Broadway running east-to-west; A through Q streets running parallel to Dorchester Street, and First through Ninth Streets running parallel to Broadway.

Following the annexation, according to O’Conner, lots that had previously sold for $400 an acre were selling at $4,000-5,000 an acre!  So begins the fascinating history of the peninsula residents call home.

To learn move about the history of South Boston, visit the South Boston Branch Library at 646 East Broadway. The library is home to a treasure trove of historical materials about South Boston.

Blog post by the Joyce Lebedew Real Estate Team.