South Boston’s Story: Dorchester Heights, Castle Island and the New Year’s Plunge
From the cannons that forced the British out in 1776 to the L Street swimmers who dive into the harbor each January, here is Southie’s history.
South Boston, known to everyone as Southie, is a neighborhood with a strong sense of itself. Its streets, beaches and monuments tell a story that runs from the Revolutionary War to a very cold New Year’s tradition.
Dorchester Neck
In the colonial era, South Boston was a peninsula called Dorchester Neck, part of the town of Dorchester. It was mostly farmland and pasture, with a high point called Dorchester Heights.
In the winter of 1775 to 1776, Henry Knox led an expedition to haul heavy artillery from Fort Ticonderoga in New York across the snowy mountains to Boston. In early March 1776, General George Washington’s troops fortified Dorchester Heights overnight and placed the cannons, which overlooked the British fleet and the town.
Facing that threat, the British army evacuated Boston on March 17, 1776. The day is still marked in Suffolk County as Evacuation Day, which conveniently shares a date with St. Patrick’s Day. A white marble monument now stands on Dorchester Heights, part of Boston National Historical Park.
Joining Boston
South Boston was annexed to Boston in 1804, and bridges soon connected it to downtown. In the 1800s, the neighborhood grew with shipyards, foundries and factories, and many Irish immigrants settled there. Triple-deckers and rowhouses filled the streets, and parish churches became the centers of community life.
Castle Island and the beaches
At the eastern tip of the neighborhood is Castle Island, the site of fortifications since the 1600s. The current granite fort, Fort Independence, dates from the 1800s. Castle Island is no longer an island, connected by land and a causeway, and its loop path, known as the Sugar Bowl, is one of the most popular walks in the city.
Along the South Boston shore, a string of beaches and the long promenade on Day Boulevard draw walkers and runners year-round.
The L Street Brownies
One of Southie’s best-known traditions takes place on New Year’s Day. Members of the L Street Brownies, a swimming group associated with the L Street Bathhouse, have taken a plunge into the frigid harbor for more than a century. In recent years, the event has also drawn crowds of participants raising money for charity.
If you plan to take part in any cold-water plunge, go with organized events that have safety staff, keep the swim very short, and talk to your doctor first if you have heart or other health concerns.
Southie today
- East and West Broadway are lined with shops, pubs and restaurants.
- Many longtime families live alongside newer residents in rehabbed triple-deckers and new buildings.
- The South Boston St. Patrick’s Day Parade remains one of the city’s largest annual events.
- The waterfront area to the north, now called the Seaport, has grown into a district of offices and housing.
On a winter day, walk the Sugar Bowl at Castle Island, then climb Dorchester Heights. Standing where the cannons were placed, you can see exactly why the British decided it was time to leave.
