Boston's Timeless Transformations
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.
The Custom House Tower
Original Use: U.S. Custom House
Current Use: Marriott Custom House Hotel and Observation Deck
Current Use: Marriott Custom House Hotel and Observation Deck
Built in 1915 atop the original 1847 Custom House, the Custom House Tower was Boston's first skyscraper, symbolizing the city's maritime power. It originally served as a government facility for processing imports and exports during Boston’s shipping heyday. The original structure, designed in the Greek Revival style, was authorized by President Andrew Jackson, and constructed between 1837 and 1847. By the time of its completion, it cost $1.1 million. In 1915, the new tower was erected, raising its height to 496 feet, where it remained the tallest building in Boston proper until 1964, when the Prudential Tower was completed.
Modern Transformation:
The building underwent a significant transformation in the 1990s after its decommissioning as a customs facility. Today, the Custom House Tower is a luxury Marriott Vacation Club property. The upper floors house time-share suites, while the iconic 26th-floor observation deck offers panoramic views of the city and remains open to the public. This adaptive reuse is a prime example of preserving history while serving the city’s robust tourism economy.
The building underwent a significant transformation in the 1990s after its decommissioning as a customs facility. Today, the Custom House Tower is a luxury Marriott Vacation Club property. The upper floors house time-share suites, while the iconic 26th-floor observation deck offers panoramic views of the city and remains open to the public. This adaptive reuse is a prime example of preserving history while serving the city’s robust tourism economy.
The Charles Street Jail
Original Use: County Jail
Current Use: The Liberty Hotel
Current Use: The Liberty Hotel
Originally completed in 1851, the Charles Street Jail was designed by architect Gridley J. F. Bryant in collaboration with prison reformer Rev. Louis Dwight. Built of Quincy granite in a cruciform layout with four radiating wings centered on an octagonal rotunda, it was Boston’s most advanced penal facility. The facility exemplified the “Boston Granite” style and embraced the Auburn Plan, prioritizing natural light, ventilation (via 33‑foot tall arched windows), segregation by inmate type, and communal work during daytime hours. Over the decades, it held both infamous and historical figures including, Mayor James Michael Curley, anarchists Sacco & Vanzetti, civil rights leader Malcolm X, suffragettes protesting President Wilson in 1919, U-boat prisoners of war, among others.
Modern Transformation:
Following its closure in 1990, the building was repurposed into The Liberty Hotel in 2007, a luxury property that masterfully blends 19th-century granite facades with modern design. The adaptive reuse preserved key architectural elements including the central rotunda and catwalks, creating a destination that’s as rich in design as it is in history. Current tenants include hospitality brands like CLINK restaurant and Scampo, helping the space function as a stylish and active commercial venue in Beacon Hill.
Following its closure in 1990, the building was repurposed into The Liberty Hotel in 2007, a luxury property that masterfully blends 19th-century granite facades with modern design. The adaptive reuse preserved key architectural elements including the central rotunda and catwalks, creating a destination that’s as rich in design as it is in history. Current tenants include hospitality brands like CLINK restaurant and Scampo, helping the space function as a stylish and active commercial venue in Beacon Hill.
South Station
Original Use: Intercity Rail Terminal
Current Use: Intermodal Transit Hub and Mixed-Use Development Site
Current Use: Intermodal Transit Hub and Mixed-Use Development Site
Opened in 1899, South Station was once the largest train station in the world, serving as the central hub for five major railroads. Its Neoclassical design by Shepley, Rutan & Coolidge made it a civic showpiece in the heart of Boston’s financial district. With a cost of $3.6 million (in 1899 dollars), it would become the busiest station in New England by 1913, and, as the first public subway in the United States, South Station offered the largest train shed in the world.
Modern Transformation:
Though partially demolished in the mid-20th century due to declining rail traffic, the headhouse was preserved and restored in the 1980s. Today, South Station functions as the Governor Michael S. Dukakis Transportation Center, accommodating Amtrak, MBTA Commuter Rail, Red and Silver Lines, and intercity buses. The site is now undergoing a transformative new phase with the construction of a 51-story mixed-use tower atop the station, led by developer Hines. The project will introduce over 600,000 square feet of Class-A office space, residential units, and retail, reinforcing South Station’s pivotal role in Boston’s future as well as its past.
Though partially demolished in the mid-20th century due to declining rail traffic, the headhouse was preserved and restored in the 1980s. Today, South Station functions as the Governor Michael S. Dukakis Transportation Center, accommodating Amtrak, MBTA Commuter Rail, Red and Silver Lines, and intercity buses. The site is now undergoing a transformative new phase with the construction of a 51-story mixed-use tower atop the station, led by developer Hines. The project will introduce over 600,000 square feet of Class-A office space, residential units, and retail, reinforcing South Station’s pivotal role in Boston’s future as well as its past.
Old City Hall
Original Use: Boston City Hall
Current Use: Office and Retail Space
Current Use: Office and Retail Space
Built on the historic site of the original Boston Latin School, Old City Hall was completed in 1865 in the French Second Empire style, housing the city’s government for over a century. It’s one of the earliest examples of monumental municipal architecture in the United States. The architectural style that Boston led the way in would soon find itself represented in various city halls up and down the East Coast.
Modern Transformation:
After city government operations moved to the new City Hall Plaza in 1969, Old City Hall underwent one of Boston’s first adaptive reuse projects. Converted into private offices and retail by the Architectural Heritage Foundation in the early 1970s, the building remains a striking example of preservation done right. In 2017, Synergy Investments acquired the building for $30.1 million. Tenants now include law firms, professional offices, and Ruth’s Chris Steak House. Located along the Freedom Trail, the building retains many original architectural elements, including its granite façade, mansard roof, and interior staircases, bringing 19th-century elegance to 21st-century commercial use.
After city government operations moved to the new City Hall Plaza in 1969, Old City Hall underwent one of Boston’s first adaptive reuse projects. Converted into private offices and retail by the Architectural Heritage Foundation in the early 1970s, the building remains a striking example of preservation done right. In 2017, Synergy Investments acquired the building for $30.1 million. Tenants now include law firms, professional offices, and Ruth’s Chris Steak House. Located along the Freedom Trail, the building retains many original architectural elements, including its granite façade, mansard roof, and interior staircases, bringing 19th-century elegance to 21st-century commercial use.
142 Berkeley Street
Original Use: Headquarters of The Youth’s Companion Magazine
Current Use: Office and Retail Building
Current Use: Office and Retail Building
Known as the Pledge of Allegiance Building, 142 Berkeley Street was the longtime home of The Youth’s Companion, the publication where the original Pledge of Allegiance was written and first printed in 1892. Designed in the Richardsonian Romanesque style, the building’s robust brick and stone architecture makes it a standout in Boston’s Back Bay.
Modern Transformation:
After The Youth’s Companion moved out in the early 20th century, the building transitioned to commercial office use. Today, it offers approximately 125,000 square feet of multi-tenant office and retail space, with high ceilings, large arched windows, and a dramatic entryway. Ground-floor tenants like Citrus & Salt add a lively street-level presence, while upper floors cater to professional services and creative firms. Its location near Back Bay Station and proximity to restaurants and shops make it a prime choice for tenants seeking a blend of historic charm and urban convenience.
After The Youth’s Companion moved out in the early 20th century, the building transitioned to commercial office use. Today, it offers approximately 125,000 square feet of multi-tenant office and retail space, with high ceilings, large arched windows, and a dramatic entryway. Ground-floor tenants like Citrus & Salt add a lively street-level presence, while upper floors cater to professional services and creative firms. Its location near Back Bay Station and proximity to restaurants and shops make it a prime choice for tenants seeking a blend of historic charm and urban convenience.
Post by
Hunneman
Jul 29, 2025