8 Best Sights in Massachusetts, USA

At the time of its construction in 1847, the Custom House was the most expensive ever built in the United States and today it is one of Boston’s most recognizable buildings. It resembles a Greek Revival temple and features an iconic tower that was added in 1915, earning it the title of the city's tallest skyscraper. Today, Marriott operates it as a hotel and vacation club, but the public can take two elevators up 26 floors to the observation deck for unparalleled views of Downtown and Boston Harbor. Tours (30 minutes) leave once daily at 2 pm; there are no tours on Friday. Tours are free, but space is limited, so call ahead to make a reservation---tours book out months in advance.

Boston's second-oldest church building might well be its most famous were it not for Longfellow's celebration of Old North Church in his poem "Paul Revere's Ride." However, Old South Meeting House is just as significant having been the site of some of the fiercest town meetings that led to the Revolution, including one on December 16, 1773, called by Samuel Adams, which led to the Boston Tea Party. The Old South's "Voices of Protest" exhibit celebrates the meetinghouse as a forum for free speech from way back then right up to the present.  This is Freedom Trail stop 8.

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.

Arlo Guthrie fans will want to make a pilgrimage to this Interfaith church used as a community gathering space and sometimes concert venue. The church, where Guthrie's famous song “The Alice’s Restaurant Massacree” began and where the movie “Alice’s Restaurant” was filmed, hosts weekly "Hootenannies," community lunches and small concerts. 

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 rotunda. It's not uncommon to see a tall ship or a charter vessel docked outside, in season. Book a free tour through the website.

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.

In the 19th century, this 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. We'll preface this by saying that the only way to see inside this amazingly historic Freedom Trail site is to order up some fast food. Sadly, that's the current role this literary gem plays, but anyone stopping by can also read the plaque on the wall that shares more about its history. From 1845 to 1865, literary lights including Henry David Thoreau, Ralph Waldo Emerson, Henry Wadsworth Longfellow, and Charles Dickens visited here where many of their works were published by James T. "Jamie" Fields (founder of Ticknor and Fields). This is Freedom Trail stop 7.