The leader of the pack is the Bernard Toale Gallery. Toale originally opened the gallery in 1992 on Newbury Street and then moved to his current digs six years later. He shows cutting edge, often quite spacey work in a range of formats including video and site-specific installations. Here is where you’ll find paintings directly on the gallery walls.
The Dona Flor ceramics gallery on Newbury Street

Photo courtesy Greater Boston CVB/ FayFoto

The Dona Flor ceramics gallery on Newbury Street, which is home to the city’s largest concentration of art galleries.

If you like Toale, you’ll also like the aesthetic of the Genovese Sullivan Gallery, which shows cutting edge work of a more whimsically abstract variety. Samson Projects has already staked out a reputation for itself showing quirky work by an international stable of up-and-coming artists as well as some better known ones, including Kiki Smith.

If you’re turned on by puckish, cheeky art then check out the Allston Skirt Gallery . It’s a tiny little space, but it packs a powerful punch of irreverent local talent. Gallery Kayafas, another small space, also crams in a lot of quirky, kinky stuff—but director Arlette Kayafas’s focus is photography.

Another thing that the South End boasts over Newbury Street are artist-run galleries: Bromfield Art Gallery and Kingston Gallery, both at 450 Harrison. Of the two, you’ll find more off-the-wall items, like huge installations that recreate the outdoors, at Kingston.

4. South Boston

South Boston, or “Southie” as it’s known to locals, was historically a working class, industrial area separated from Boston proper by the Fort Point Channel. In the past few years, as rents skyrocketed elsewhere in the city, young artists discovered that Southie’s waterfront warehouses contained ideal spaces to work and live. Inevitably, developers also took notice and the area began gentrifying—a trend solidified by the opening of Diller Scofidio + Renfro’s new building for the Institute of Contemporary Art—but its arts scene retains some of the earlier pioneering spirit.

Fort Point is an area bounded to the west by the waterway, to the north by Summer Street, and to the east by A Street. It’s served by the T but, unless you like walking long distances on windswept streets with little to offer in the way of amenities, you’re better off traveling by car. The neighborhood contains a number of small galleries and artist studios, most of which belong to the Fort Point Arts Community. In addition to maintaining a gallery at 300 Summer Street, in a recently developed warehouse-style building, this collaborative sponsors an annual Art Walk each May that gives visitors a chance to tour the digs of neighborhood artists.

Further afoot in Southie, in a large building at 516 East Second Street, is a similar collaborative called the Artists Foundation, which also operates a small gallery; the building is also home to a relative newcomer called the Second Gallery, which is making waves with in-your-face installations by promising local talent.

5. Cambridge

Although Cambridge, Massachusetts, just across the Charles River from Boston’s Back Bay neighborhood, is a separate city it bills itself as “Boston’s Left Bank.” Just like in Paris’s intellectual quarter, in Cambridge you’ll find several world-class schools: including Harvard University and the Massachusetts Institute of Technology (MIT). Massachusetts Avenue, the city’s main drag, runs from one school to the other.

For visitors, the heart of Cambridge is Harvard Square—also the heart of the university. It centers on a small plaza where, in warm and cold months alike, you’ll find a motley collection of buskers and skateboarders. Cafés, bookstores, and clothing shops line the square—many of them independently owned, although chain stores have encroached in a major way. But not everything in Cambridge revolves around Harvard. Central Square—which is something of a misnomer because there is no square to speak of, is closer to MIT and offers a more eclectic, authentic mix of cheap eats and dollar stores.

Cambridge’s gallery scene is small and sporadic compared to Boston, but you’ll always find something edgy at Art Interactive. Located in Central Square, this space is guest-curated and offers educational symposia about the artists as well as opportunities to go behind the scenes. The gallery’s mission is to encourage public participation: in keeping with its focus on fluxus art, happenings, underground art, and performance pieces. The spirit of the 1960s is alive and well here, but often with a new, digital twist.

Other Cambridge art venues include the Stebbins Gallery, just off Harvard Square in the Zero Church, and the Cambridge Artists’ Co-op, down a side street from Stebbins, both offering a hit-or-miss mixture of crafts and what could be termed “outsider art.” More reliable are two small galleries associated with the Cambridge Art Association, near Harvard Square, and Out of the Blue Gallery, north of Central Square on Prospect Street.