A totem pole depicting a leprechaun stands on top of two boxes of tea in downtown Boston. In his hands is a musket and on his head a Puritan-style brimmed hat overflowing with a cornucopia of lobsters, Samuel Adams beer and a squirrel that might or might not be urinating. Entitled “Material Monument to Thomas Morton (Playing Indian)”, the 4.25-metre-tall sculpture by artist collective New Red Order pokes fun at two of the city’s sacred cows: its Irish diaspora and the Boston Tea Party. Placed outside Faneuil Hall, a meeting place for American Revolutionary War-era protests, the installation is the work of Kate Gilbert. As the executive director of the first Boston Public Art Triennial, which opened on 22 May and runs until 31 October, she’s pushing the buttons of a city that is known for its intellectualism but also a certain aesthetic conservatism.

“Our visual culture doesn’t represent how rich our assets are here,” Gilbert tells Monocle. Until Halloween, Bostonians will be able to gaze upon 20 newly commissioned works, from larger-than-life sculptures to delicate textiles woven between trees, all of which are designed to spark curiosity and debate – and none is a milquetoast crowd-pleaser. They are dispersed equally between upmarket and less affluent precincts, outside marquee museums and in under-visited parks, in order to encourage residents to explore beyond their usual neighbourhoods.

Gilbert, who moved to Boston nearly 30 years ago, is uniquely qualified to pull off an event that has the potential to put New England’s largest city on the global contemporary-art map. As a young painter, she was part of the scrappy artist community that fought with city hall over redevelopment schemes in the Fort Point warehouse district. That early taste of urban planning ultimately led her to advocate for art from inside the establishment during a pivotal moment in Boston’s recent history: the removal of an elevated highway through the city centre to be replaced by a park. “You’ve got a mile and a quarter of found land,” she says. “When does that ever happen in an old city like this?”

When the Rose Kennedy Greenway opened in 2008, few knew what to do with it. As a member of the green space’s conservancy, Gilbert spearheaded the cultural component, starting with a lavish $500,000 (€441,000) opening bash. “If you’re going to open a new park, that party should signal the values and the sort of vision for what you want that park to be and how people will use it,” she says. The opening included a temporary installation of bears made from timber and rusted steel. Children loved the bears and the area’s residents began using the park as a landmark. Emboldened, Gilbert helped secure a prominent canvas across from the city’s main train station for Brazilian street-art duo Os Gêmeos in 2011.

In 2015 she launched Now + There, a public art entity, and has spent the past 10 years acclimatising Bostonians to increasingly challenging work. “It has been an acculturation process,” she says. “Now people aren’t afraid of contemporary art.” The public’s willingness to play along is also a boon to the creative community, as local art schools mint graduates who might be more inclined to make a career in Boston if they see opportunities. Roughly half of the triennial’s artists live or work in the city, with the rest hailing from further afield – Berlin, Los Angeles, Rio de Janeiro, Alaska. “A measurable outcome is that artists will stay here,” she says, noting that the city ranked third in a 2024 index of the most vibrant US cities for their sector. A large part of that is down to her efforts.