Why go
South Boston runs southeast from Fort Point Channel to Castle Island and Dorchester Bay. For visitors, its best asset is the shoreline: a nearly continuous run of public beaches and paved paths along Day Boulevard that ends at Castle Island, where a 19th-century granite fort looks out over the harbor toward the runways at Logan. Inland, the neighborhood climbs to Dorchester Heights, where George Washington’s cannon forced the British out of Boston in 1776, and spreads across a grid of triple-deckers and rowhouses cut by Broadway, the main street.
Southie has long been known as a working-class Irish American neighborhood, and in recent decades it has also drawn young professionals and families, so old pubs and parish halls now sit next to condos and sit-down restaurants. It is a place people live, not a showpiece. Come for the water, the walk and a meal. If you want museums and historic houses, spend your day downtown instead.
Getting around
The Red Line stops at Broadway and Andrew, both accessible, on the neighborhood’s western side. From there, buses do the rest. Route 9 (City Point to Copley Square) runs the length of Broadway from Broadway station. Route 11 starts on Chauncy Street near Downtown Crossing and runs by South Station and Broadway station to City Point. Route 7 runs from Otis and Summer streets downtown along Summer Street through the Seaport to City Point, and Route 10 connects Andrew with City Point. The City Point Bus Terminal is a short walk from Castle Island.
The shoreline path along Day Boulevard is flat and good for bikes, strollers and wheelchairs. The streets inland climb toward Dorchester Heights, and the monument’s observation deck is reached only by stairs, 72 steps and then a 20-step spiral. Bluebikes has docks at Broadway station, on West and East Broadway and along Day Boulevard near the beaches.
When to go
Summer is beach season, when Castle Island and the loop are at their busiest and Sullivan’s lines are long. Late September and October are quieter and still good for the waterfront walk. In winter the path stays open and the wind comes straight off the harbor.
The neighborhood’s biggest day is the St. Patrick’s Day/Evacuation Day Parade, run by the South Boston Allied War Veterans Council on the Sunday nearest March 17, which is both St. Patrick’s Day and Evacuation Day. Expect very large crowds and street closures, and take the T. On New Year’s Day, the L Street Brownies swim.
A short history
South Boston began as Dorchester Neck, a thin spit of land belonging to the town of Dorchester. On the night of March 4, 1776, the Continental Army dragged cannon onto Dorchester Heights, and on March 17 the British evacuated Boston. In 1804 the Neck became the first piece of Dorchester ceded to Boston, and landfill gradually widened it. Castle Island, fortified since 1634, was finally joined to the mainland by the late 1920s.
From the mid-1800s, Irish immigrants settled here in large numbers and South Boston became a working-class neighborhood, with jobs on the waterfront and in factories such as Gillette. Thomas Park was laid out on the Heights in the 1850s and the monument followed in 1902. In recent decades, rising housing costs and the growth of the Seaport next door have changed who lives here.
Local tips
- For Castle Island without a car, take Route 11 from Chauncy Street by Downtown Crossing, or Route 7 from Summer Street, straight to City Point. No transfer needed.
- Walk the Pleasure Bay loop first and finish at Sullivan’s.
- Bring a layer to Castle Island, even in summer.
- The grounds at Dorchester Heights are open daily, but the tower opens only for special events, so don’t plan the day around a climb.
- On parade Sunday, arrive early by T and expect to walk. Driving in is not worth it.
