South End, Boston, MA

Despite, or perhaps because of, its history as a rough-around-the-edges area, the South End has emerged in recent decades as one of Boston’s trendiest neighborhoods.

Since the 1970s, the area has been cited for its artistic, cultural, and gay-friendly environment and for organizations like the South End Artists Guild (SoWa), which have pushed the area to prominence on the Boston art scene with events like monthly gallery crawls and design markets.

Not known for charming architecture, the neighborhood does offer serviceable red brick row houses that have become popular with young professionals and recent grads – a population surge that’s been met with the opening of many independently-owned restaurants and bars throughout the district.

Although the area has maintained its ethnic and cultural diversity and – in some areas – its characteristic roughness, South End’s gentrified nature has made it a daytime destination for upper-middle-class shoppers and a nighttime spot for diners looking for a unique night out.