9 Best Sights in Boston, Massachusetts

This is the second-oldest church building in Boston, and were it not for Longfellow's celebration of Old North in "Paul Revere's Ride," it might well be the most famous. Some of the fiercest of the town meetings that led to the Revolution were held here, culminating in the gathering of December 16, 1773, which was called by Samuel Adams to confront the crisis of three ships, laden with dutiable tea, anchored at Griffin's Wharf. The activists wanted the tea returned to England, but the governor would not permit it—and the rest is history. The Voices of Protest exhibit celebrates Old South as a forum for free speech from Revolutionary days to the present.

This Colonial-era landmark has one of the most recognizable facades in Boston, with its gable adorned by a brightly gilded lion and silver unicorn, symbols of British imperial power. This was the seat of the Colonial government from 1713 until the Revolution, and after the evacuation of the British from Boston in 1776 it served the independent Commonwealth until its replacement on Beacon Hill was completed in 1798. The Declaration of Independence was first read in public in Boston from its balcony. John Hancock was inaugurated here as the first governor under the new state constitution. Today, it's an interactive museum with exhibits, artifacts, and 18th-century artwork, and tells the stories of Revolutionary Bostonians through costumed guides. This is Freedom Trail stop 9.

In the early 1970s, the tallest building in New England became notorious as the monolith that rained glass from time to time. Windows were improperly seated in the sills of the blue rhomboid tower, designed by I. M. Pei. Once the building's 13 acres of glass were replaced and the central core stiffened, the problem was corrected. Bostonians originally feared the Hancock's stark modernism would overwhelm nearby Trinity Church, but its shimmering sides reflect the older structure's image, actually enlarging its presence. Renamed from the John Hancock Tower to 200 Clarendon in 2015, the building is mostly offices and remains off limits to the public.

If you like nothing better than to imagine how the other half lives, you'll suffer no shortage of old homes to sigh over in Boston's Back Bay. Most, unfortunately, are off-limits to visitors, but there's no law against gawking from the outside. Stroll Commonwealth, Beacon, and Marlborough streets for the best views. For details on lectures, films, and other events offered in some of these respected institutions, see the free, biweekly Improper Bostonian and the Boston Globe's art section or calendar listings.

One of Boston’s most recognizable buildings, the gorgeous 1847 Custom House resembles a Greek Revival temple and features an iconic tower that was added much later, in 1915. This addition gave the building notoriety at the time as the city’s tallest. Where the skyscraper once operated as a federal building, today, Marriott owns it as a hotel and vacation club. The public is invited into the Custom House’s recently renovated 26th-floor observation deck for unparalleled views of Downtown and Boston Harbor daily at 2 pm, except Friday. Entrance is free, but space is limited, so call ahead for a ticket at least 48 hours in advance.

This massive Romanesque structure was built in 1884 as a temple for the Working Union of Progressive Spiritualists. Beginning in 1914, it enjoyed a long run from 1914 to 1984 as a movie theater, then served a turn as a bookstore. Today, it's home to a private school.

Believe it or not, the public is welcomed in for a visit to this architectural wonder and federal house of justice. Galleries across the courthouse feature rotating exhibitions on a variety of themes, from maritime history to the judicial system. Don't miss Ellsworth Kelly's permanent installation The Boston Panels in the courthouse's entry rotunda. It's not uncommon to see a tall ship or a charter vessel docked outside, in season. You can also book an hour-long Discovering Justice tour.

Built in 1865, Old City Hall is a historic site and served as the municipal seat of government for 38 of Boston's mayors, including famous ones like John "Honey Fitz" Fitzgerald, James Curley, and Kevin White. In its courtyard, find Richard S. Greenough's bronze statue of Benjamin Franklin and a mural marking the original site of the Boston Latin School. Today, Old City Hall is an office building. While you can't really venture too far inside the building, do go up and check out the murals around its entrance.

Through these doors, between 1845 and 1865, passed some of the century's literary lights: Henry David Thoreau, Ralph Waldo Emerson, and Henry Wadsworth Longfellow—even Charles Dickens paid a visit. Many of their works were published here by James T. "Jamie" Fields, who in 1830 had founded the influential firm Ticknor and Fields. In the 19th century, the graceful, gambrel-roof, early-Georgian structure—built in 1718 on land once owned by religious rebel Anne Hutchinson—also housed the city's leading bookstore. There's a plaque on the wall to read more about its history, but today, somewhat sadly, the building is home to a fast-food joint. This is Freedom Trail stop 7.