Boston’s skyline is a living timeline, where centuries-old granite facades and copper domes coexist with steel-and-glass towers. But some of the city's most iconic structures aren’t just preserved, they’ve been reimagined.
Across Boston, a remarkable trend of adaptive reuse has given new life to historic buildings, honoring their architectural and cultural legacies while reinventing their roles in the modern urban fabric. From once-imposing government facilities and train terminals to jails and publishing houses, these buildings have transitioned into vibrant hotels, offices, restaurants, and residential towers. Their stories reveal more than just architectural evolution—they reflect Boston’s ability to blend heritage with innovation, resilience with reinvention.
Below, we explore five standout examples: The Custom House Tower, Charles Street Jail, South Station, Old City Hall, and 142 Berkeley Street. Each one tells a unique story of transformation, offering a powerful look at how Boston continues to build its future on the foundations of its storied past.