As the city of Boston expanded outwards from Beacon Hill and the North End, the next logical place to populate was the southern end of the Shawmut Peninsula. In the late 19th century, then, the South End quickly became the place to see and be seen, and rich merchants and ship captains built large brownstones on its waffle-iron layout of streets.

Literally made of large brown stones, these homes were distinguished from the smaller brick buildings on Beacon Hill by their larger rooms and high ceilings, frequently with tall stairways leading up to the entrance door on the second floor (an assurance against flooding). Nearly as quickly as they colonized it, however, the fickle abandoned the South End in favor of the Back Bay, which was newly reclaimed from landfill in the river and built on an even grander scale than its neighbor.

For more than 100 years, the South End neighborhood was a melting pot of various immigrant groups who occupied the buildings left behind by the bourgeoisie, and it achieved a reputation for being a rough-and-tumble area. That reputation is hard to imagine now as the neighborhood reaches the height of a long, slow gentrification that began in the 1970s when it was rediscovered, primarily by artists and middle-class gay men and lesbian women.

The South End neighborhood is still the center of Boston’s GLBT population, and it’s not unusual to see rainbow flags proudly fluttering from the upper stories of brownstones. The neighborhood also has a pleasing mix of residential and commercial uses, with the busiest streets of Tremont and Columbus lined with intimate (and expensive) neighborhood restaurants and storefronts occupied by boutiques selling $100 T-shirts and cutting-edge alternative fashion.

In the late 1990s, the South End expanded even farther southward past its historical boundary of Washington Street to create a brand-new neighborhood cheekily called SoWa (South of Washington). All of the available land in one of downtown’s last frontiers has quickly been snatched up by modern loft apartment buildings that give the street an in-the-moment vibe. The area appeals to a certain intersection of art and commerce, with some of the city’s edgier galleries cheek-by-jowl with its hotter new restaurants. Thus far, however, it has retained a certain grittiness that has forestalled its complete gentrification.