South End v. South Boston: A Guide to Two Neighborhoods

"South" is where the similarities end for these two Hub neighborhoods.

We break down two Boston neighborhoods that regularly confuse out-of-towners. The similarities end at “South.”

South Boston

South Boston aka 'Southie'

Compared to Beacon Hill or the North End, South Boston is mega-sized. The neighborhood sits directly to the south and east of downtown, and includes sub ‘hoods such as Fort Point and the Seaport District, Telegraph Hill, West Broadway and City Point. South Boston is famously Irish and blue collar.

What It Looks Like: Stunning views of Boston Harbor contrast with triple-deckers, churches and gritty watering holes. The more northern end of South Boston has industrial roots, so it’s occupied by converted factories and empty lots now under development.

Attractions of NoteCastle Island, a historic park surround on three sides by saltwater that’s absolutely packed in fair weather. Joggers do the Loop (technically the Head Island Causeway, though no locals call it that) and families grab a burger and soft serve from Sullivan’s. Beaches line Pleasure Bay and Old Harbor on Dorchester Bay. The Dorchester Heights Monument near E. Eighth and Dorchester streets is part of Boston National Historical Park. Attractions in the Seaport District include Blue Hills Bank concert venue, Harpoon Brewery, the Boston Children’s Museum and the Institute of Contemporary Art/Boston.

Notable Residents: James ‘Whitey’ Bulger, David Lindsay-Abaire, Raymond Flynn

The Crowd: Over the last decade, affluent young professionals have infiltrated South Boston, scooping up renovated waterfront multi-families along Day Boulevard and new luxury condos near West Broadway. But, there’s also a healthy mix of lifers—people whose parents and grandparents grew up in Southie, too.

Late-Night Scene: Alcohol-fueled; Countless bars line both West and East Broadway, attracting a post-college crowd that enjoys mingling and throwing back a few brewskies. The Seaport District scene is more restaurant-based and caters to a slightly older crowd.

Getting here: The MBTA’s Silver Line or Red Line, or take an Uber

South End

Arts and culture thrive in the South End. Many artists live and work in the neighborhood, particularly in SoWa (south of Washington Street). The South End sits south and west of downtown, across I-93 from South Boston, and is an easy walk from the Back Bay.

What It Looks Like: Brick rowhouses populate tiny, tree-lined streets. In fact, the South End is actually on the U.S. National Register of Historic Places as the largest intact Victorian row house district in the country. Flowering parks enclosed with wrought-iron fencing pop up with frequency. SoWa boasts a number of dilapidated mills that have been/are being reworked to house art galleries and studios, apartments, small design businesses and restaurants. 

Attractions of Note: Boston Center for the Arts campus, including the Calderwood Pavilion, the Cyclorama and the Mills Gallery. SoWa District art galleries and studios. Cathedral of the Holy Cross. South End Open Market

Notable Residents: Henry James, Louisa May Alcott, Martin Luther King Jr., Malcolm X

The Crowd: Residents are a mix of creative types, yuppie families, LGBTQs and a small but vibrant Latino community. The ‘hood attracts art lovers and others looking for design inspiration, whether at official design firms or at home furnishings boutiques. South Enders also love to socialize and do so over good food and drink crafted by award-winning chefs and mixologists at dozens of restaurants where cooking styles span the globe. 

Late-Night Scene: Restaurants are a big draw for foodies and since reservations are often hard to come by, expect to eat super early or very late. Theater is also big; Boston Center for the Arts usually has a show running on one of its four stages. The South End’s gay culture means some restaurant bars and a few devoted clubs bring in LGBTQs from around the city.

Getting here: Silver Line or Orange Line, or walk it easily from Back Bay and Chinatown

A Map of South Boston and South End's Attractions

Leigh Harrington
About the author

Leigh formerly served as the Boston editor for Where and was the br...