The heart of the American Revolution, Boston became home to midnight rides and at least one wild tea party. Yet this spirit of rebellion is tempered by a deep conservatism that has shaped the urban landscape since the 19th century. Drive through the South End, with its rows of Victorian-era townhouses, or up past the brick federals on Beacon Hill, and you might begin to think that the independent spirit of the city’s founders lives on mostly in the local driving habits.

Now, galvanized by the Big Dig—the nearly $15 billion effort to push underground a grim elevated highway that cut through downtown—Boston is undergoing the most radical urban changes in its history. Not only has the city center been reunited with its waterfront for the first time in 50 years, but the reclaimed land along the shore is being developed into a greenway (albeit with less green than originally expected). In a ripple effect, the Seaport District, a wasteland of parking lots on the far side of the highway, is being redeveloped along with the South Boston waterfront, where old industrial buildings are being converted into lofts and restaurants.

Alongside these megaprojects, smaller-scale change is transforming the neighborhoods that make up metropolitan Boston. With no room left to grow in Cambridge, Harvard University is expanding across the river into Boston’s Allston neighborhood. Up the river, a building boom at and around MIT has produced Frank Gehry’s Ray and Maria Stata Center, Steven Holl’s Simmons Hall dormitory, and Behnisch, Behnisch & Partner’s Genzyme Center, which pushed the envelope on green building.

Bostonians typically cast a skeptical eye on urban change. When the oil company Citgo tried in 1983 to dismantle its corporate neon sign, opponents mobilized to have it declared a historic landmark. More recently, defenders and critics of City Hall have come to blows over its 1960s Brutalist-style architecture. And the Big Dig is not exempt: Before the delays and the cost overruns, and long before a woman was killed in the collapse of part of a new tunnel last summer, civic discontent had convinced the transportation department to erect a sign reading, “Rome wasn’t built in a day. If it was, we would have hired its contractors.” But what kind of city will Boston be when the hard hats go home? It’s a question of great interest to Nicholas Baume, chief curator of the new Institute of Contemporary Art.