As our design team knows best, inspiration is everywhere, from the iconic storefronts of New York’s Fifth Avenue to the tiniest architectural element of a stylized archway. Boston, the beloved city our design team calls home, is the largest in New England and one of the most historic cities in America. Boston architecture is rife with historical significance. The city as we know it today was first inhabited by Native Americans dating back to at least 2400 BC. Centuries later, in 1630, the Puritans arrived, founding Massachusetts Bay Colony and the City of Boston, as well as Harvard University and Boston Latin School, where Benjamin Franklin, Samuel Adams, and John Hancock studied. 

Known as the place of monumental events like the Boston Tea Party and key battles of the Revolutionary War, Boston is teeming with must-see architectural treasures that span centuries. Skyscrapers from the modern era tower over 18th-century brick buildings, characterizing a perfect juxtaposition of the old and the new. 

We’ve compiled some of our favorite examples of Boston architecture to see across the city, all accessible by foot. For a walking tour of architectural marvels that inspire our team, find a pair of comfortable walking shoes and map out your tour with these stops along the way. 

1. The Institute of Contemporary Art/Boston (ICA)

Year Opened: 2006
Location: 25 Harbor Shore Drive, Boston

Our Boston architecture tour starts in the up-and-coming Seaport District of Boston, home to one of the city’s most famous art museums: The Institute of Contemporary Art (ICA). First established as the Boston Museum of Modern Art in 1936, it “captures the stimulation of contemporary culture and excitement,” according to the ICA. 

The building was designed by award-winning architects Diller Scofidio + Renfro “from the sky down” and “from the ground up,” to contemplate art and allow for the public to enjoy dynamic spaces, respectively. A combination of interior and exterior space grants visitors shifting perspectives of the waterfront. It’s considered a “poetic gathering space and harborside icon” by Architect Magazine – and we couldn’t agree more.

2. South Station

Year Opened: 1899
Location: 700 Atlantic Avenue, Boston

About a fifteen-minute walk from the ICA, across the Evelyn Moakley Bridge, is Boston’s South Station. Officially known as The Governor Michael S. Dukakis Transportation Center at South Station, it’s the largest railroad station and intercity bus station in the city. The building, with its symmetry and stone facade, can be categorized as Neoclassical architecture. At the top of the main head house is the iconic South Station clock, styled after London’s Big Ben. Considered a “hallmark of the bygone era,” it’s one of our turn-of-the-20th-century favorites. As far as Boston architecture is concerned, we love this turn-of-the-century stalwart of transportation.

3. Western Union Building (Art Deco Dunkin’ Donuts)

Year Opened: 1930
Location: 230 Congress Street, Boston

Four minutes from South Station is an Art Deco wonder of Boston architecture, located in the city’s Financial District on Congress Street. Known as the Western Union Building (and locally dubbed the “Art Deco Dunkin’ Donuts”), this twelve-story steel frame skyscraper is distinct for its Art Deco geometric decoration, marble, and marquee lettering. 

The high rise’s exterior is reminiscent of Egyptian and Mayan art, Cubism, Fauvism, and Expressionism, as noted by Boston Magazine. Even better: its side entrance, 230 Congress Street, is where donuts and coffee are sold to fuel Boston’s busiest finance folks. We think 20 minutes of walking calls for a snack.

4. Custom House Tower

Year Opened: 1915
Location: 3 McKinsley Square, Boston

Next on our list is the Custom House Tower. Walk another nine minutes through the Financial District and you’ll land at the entrance to this Boston jewel (but you’ll likely have spotted the skyscraper already). Located in McKinley Square, it was designed in the Greek revival style by 19th-century American architect, Ammi Burnham Young, and completed in 1915. It stands 496 feet tall, and was added to the National Register of Historic Places in 1973. It’s currently home to the Marriott Custom House Hotel.

5. Quincy Market

Year Opened: 1826
Location: 206 S. Market Street, Boston

Anyone who’s ever visited Boston will likely recommend a visit to Quincy Market (and to try some of its fun local eateries). Just two minutes away from the Custom House Tower, it’s a great place to stop for lunch while you continue your walking tour of Boston architecture. The indoor market near Faneuil Hall was named after Mayor Josiah Quincy, who had it constructed, and it was registered as a Boston Landmark in 1996. Quincy Market is one of the largest market complexes built in the first half of the 19th century, and also is characterized by the Greek Revival style.

6. Faneuil Hall

Year Opened: 1743
Location: 4 S. Market Street, Boston

Dubbed one of America’s most visited tourist sites by Forbes, Faneuil Hall was established before the Revolutionary War. Built in 1742 and just about a one-minute walk from Quincy Market, Faneuil Hall is a renowned marketplace and meeting hall in Government Center. Historic figures like Samuel Adams and others made speeches here to encourage America’s independence from Great Britain. 

Notable elements of the building include its bell and grasshopper weather vane, as well as its statue of Samuel Adams that’s towered out front since 1880. Now part of the Freedom Trail (another walking trail to explore here), Faneuil Hall is sometimes called “the Cradle of Liberty,” a must-see for any Boston architectural tour.

7. Old State House

Year Opened: 1713
Location: 206 Washington Street, Boston

A four-minute walk away from Faneuil Hall, adjacent to the site of the 1770 Boston Massacre, is Boston’s Old State House. The Massachusetts General Court sat in this Georgeon-style building from 1713 through 1798. On July 18, 1776, Son of Liberty Col. Thomas Crafts proclaimed the Declaration of Independence from the east side balcony of the building.

The Old State House is one of the oldest public buildings in the US and the oldest surviving building in Boston today. Today, it’s a museum that covers the important history of the city, and was registered as a Boston Landmark in 1994.

8. Paul Revere House

Year Built: 1680
Location: 19 North Square, Boston

Heading to the North End, we’ll walk another ten minutes to the Paul Revere House, built in 1680 and the oldest house in downtown Boston. Indeed, this was once the home of American patriot Paul Revere during the American Revolution (he owned the house from 1770-1800). Now a nonprofit museum, this remarkable house was rightfully dubbed a National Historic Landmark in 1961.

9. Old North Church

Year Built: 1723
Location: 193 Salem Street, Boston

Also located in Boston’s North End, just five minutes from the Paul Revere House, is the Old North Church. This church is particularly notable as it’s said to have been the location where the “One if by land, two if by sea” signal on Paul Revere’s midnight ride of the American Revolution was sent. Currently the oldest standing church in Boston, the Old North Church is a National Historic Landmark. The Georgian-style building was inspired by British architect Christopher Wren’s work, who rebuilt London after the Great Fire.

10. Skinny House

Year Built: c. 1870s
Location: 44 Hull Street, Boston

A two-minute walk down Hull Street from Old North Church will bring you to the Skinny House. We consider this one of the most charming (and perhaps sassiest) buildings on our tour. The Skinny House is a narrow four-story home which the Boston Globe called “the narrowest house in Boston. It was originally built as a spite house following the American Civil War. Spite houses were built out of ‘spite’ to irritate neighbors with land stakes. 

As spite houses weren’t built for long-term living, they were often irregularly shaped – and the Skinny House one certainly fits those characteristics. The house is only ten feet, four inches wide, complete with only five doors inside. As of 2005, it was privately owned and went back on the market in 2017.

11. Old City Hall

Years Built: 1862-65
Location: 45 School Street, Boston

Next on our tour is the Old City Hall, which requires about a 20-minute walk back through the downtown area. This City Hall served as the seat of the city council from 1865 to 1969. The building is quite interesting, as it was one of the first designed in the French Second Empire style in the United States. The Old City Hall paved the way for other public buildings to be constructed in the same style throughout Boston and the nation (i.e. the Old Executive Office Building in Washington, DC). Prior to its construction, the site of the Old City Hall was where the Boston Latin School once stood and operated from 1704 to 1748. 

12. The Massachusetts State House

Years Built: 1795-98
Location: 24 Beacon Street, Boston

The 23k gold-domed Massachusetts State House, also called the New State House, is the current state capitol and seat of the state’s government. Located in the Beacon Hill neighborhood (if you have time, peruse the streets of this quaint area to see gorgeous townhouses and charming streets), the State House was designed by architect Charles Bulfinch and completed in 1798. This marvel, just six minutes from the Old City Hall, is considered a masterpiece of Federal architecture, and therefore makes the list of National Historic Landmarks. It was also built on land once owned by John Hancock (more on him below).

13. Opera House

Year Opened: 1928
Location: 539 Washington Street, Boston

The Boston Opera House, or the Citizens Bank Opera House, was originally built as a movie and live vaudeville theater when it opened in 1928, but showed only films starting the following year. It remained the city’s most popular movie theater for the two decades that followed. The Opera House, first called the Keith’s Memorial Theatre, was one of the most elaborate designs of 20th-century theater architect Thomas W. Lamb. This iconic example of Boston architecture makes our list not just for its historical significance, but for its ornate and absolutely breathtaking French- and Italian-style interior. It is only a nine-minute walk from the State House.

14. Trinity Church

Years Built: 1872-77
Location: 206 Clarendon Street, Boston

Through the Boston Common and down Clarendon Street is Trinity Church, just seventeen minutes walking from the Opera House. Located in Boston’s Back Bay, the congregation was founded in 1733. Its original site on Summer Street burned in the Great Boston Fire of 1872, so it was rebuilt on this location from 1872 to 1877. It’s a noteworthy architectural example as it’s the “birthplace and archetype of the Richardsonian Romanesque style,” which consists of clay roofs, polychromy, heavy arches, and a large tower. Following its creation, the style spread across the nation.

15. John Hancock Tower

Year Opened: 1976
Location: 200 Clarendon Street, Boston

Four minutes of walking will find you at our next stop, The John Hancock Tower (locally called “The Hancock”). Now called 200 Clarendon Street, it stands at a whopping 62 stories high (that’s 790 feet). Designed by Henry N. Cobb, it was completed in 1976 and is one of our more modern must-sees. In 1977, the tower’s firm was awarded the National Honor Award by the American Institute of Architects. It’s been Boston’s tallest building, and the tallest in New England, since it opened. 

The skyscraper was dubbed The John Hancock building because its main tenant was originally John Hancock Insurance, which partially relocated in 2004. And John Hancock, the company’s namesake and an American patriot of the Revolution, is most famous for his large and noticeable signature on the Declaration of Independence. 

16. Boston Public Library

Year Established: 1852
Location: 700 Boylston Street, Boston

Another must-see of the city is the Boston Public Library, just six minutes away from The John Hancock tower. This renowned library was founded in 1848 and established in 1852. Currently, it contains about 24 million volumes (including John Adams’ personal library and early Shakespeare editions) and electronic resources, which makes it the third largest public library in the country. 

The building was expanded in 1880, with new additions built in a Renaissance style based on the Bibliotheque Ste-Genevieve in Paris. The library was designated a Boston Landmark in 2000, and today remains a common place for visitors and residents alike to visit, study, read, and relax among desks dotted with green lamps in the Reading Room. 

17. Prudential Tower

Years Built: 1960-64
Location: 800 Boylston Street, Boston

About a nine-minute walk down Boylston Street brings us to yet another modern skyscraper worth looking up for: Prudential Tower, colloquially called “The Pru.” This international building is part of the Prudential Center complex, and it’s the second tallest building in Boston (after The John Hancock). The Pru was built for Prudential Insurance, and stands 759 feet tall, and contains 52 floors and 1.2 million square feet in commercial and retail space. Our favorite part of this tower is the 50th-floor observation deck (take a look at how that’s being reenvisioned here). Today, this building is known among city-dwellers to be the place where sports wins, major events, and charities are commemorated with lit up signs displayed prominently at the top.

18. Mass Art, Tree House Residence Hall

Years Built: 2010-2012
Location: 578 Huntington Street, Boston

While there are many, many more architectural wonders to see in Boston, we’ll end our walking tour with this modern marvel. About 21 minutes away from the Prudential Tower, the Massachusetts College of Art and Design’s Tree House Residence Hall paves the way for modern, sustainable high rises further juxtapose the new and old across the city.

This innovative tower was first proposed to solve for the unique learning and living requirements of art school students, and was inspired by Gustav Klimt’s 1909 painting, Tree of Life. The building contains 493 beds for the College’s first-year and sophomore students, a ground floor cafe and living room, a health center, and a “Pajama Floor” with a communal kitchen and game room. The Tree House’s curved stone base features an underground tunnel that navigates through the site.

This building is especially unique for its symbol of harmony. It was designed and constructed in a collaborative manner, taking into consideration the opinions of students, administrators, professors, alumni, neighbors, and more. On its exterior is 5,000 aluminum panels that create a mosaic to represent tree bark, along with green window panels that resemble leaves. And while the building has many eco-friendly features, it was awarded a Silver LEED certification by the US Green Building Council, because “its energy usage is 22 percent more efficient than code mandates.” 

Here’s hoping that the future of modern building in Boston is even more sustainable and equally as artful and inspiring as this one.