At Go Ahead Tours, we’re proud to call the beautiful Boston area our home—there’s an endless amount of history and culture packed into one walkable (and bikeable!) city.
The Freedom Trail is the easiest way to see a number of historical landmarks in one day. Just follow the red line painted on the street and you’ll pass by some of the city’s most iconic buildings in the 2.5-mile trail that spans from downtown to Charlestown. You can start anywhere, but the official beginning is found at the Boston Common Visitors Center, where plenty of maps are available for purchase alongside souvenirs and books—we recommend picking up a copy of Charles Bahne’s Complete Guide to Boston’s Freedom Trail if you’re opting for a self-guided tour. Read on for some of our favorite hometown historic sites you’ll find along the trail.
Massachusetts State House
A major stop on the Freedom Trail, the “New” State House was built in 1798 on the land once used as John Hancock’s cow pasture. The building’s signature dome was originally made of wood before it was covered in copper by Paul Revere himself. In 1874, 23-karat gold leaf was applied to give it the shine we see today—though it was briefly painted black during WWII. Want the in-depth history of the whole building? Free tours of the interior are offered daily.
Faneuil Hall Building
Built in 1742 by wealthy merchant Peter Faneuil, the name of this marketplace and meetinghouse has become somewhat of a catch-all term for the surrounding neighborhood full of popular shopping and nightlife. The historic building itself is worth a stop, though, as its Great Hall has provided space for many historic meetings, including protests of the Sugar Act and Stamp Act in 1764, the Sam Adams-hosted funeral for victims of the Boston Massacre and Daniel Webster’s legendary eulogy of John Adams and Thomas Jefferson.
Paul Revere House
Revere lived in this wooden structure at the time of his storied ride to Lexington, along with his mother, wife and many of his children (he had 16 in all). Dating back to 1680, the structure is downtown Boston’s oldest building currently standing.
Old South Meeting House
Officially a Puritan house of worship, the Old South Meeting House hosted the legendary meeting on December 16, 1773 regarding the taxation of tea. When Samuel Adams declared “Gentlemen, this meeting can do nothing more to save the country,” attendees marched to Griffin’s Wharf where 340 crates of tea were ceremoniously dumped into the harbor.
Bunker Hill Monument
Misinformation abounds when it comes to the Battle of Bunker Hill. Firstly, the battle technically took place on Breed’s Hill, an error possibly attributed to mislabeled British maps or simply the fact that Colonel Prescott was ordered to fortify Bunker Hill but chose Breed’s instead. Secondly, the battle is known as a turning point in the Revolutionary War, showing that the colonists could hold their own against the Red Coats despite dwindling stores of ammunition—with many forgetting that the British technically won the face-off. The iconic obelisk has stood on the site since 1842, and a free historical museum opened across the street in 2007.
Old North Church
The alias of Christ Church, Old North Church is the oldest standing church building in Boston. Its steeple was home to the signal lanterns immortalized in Longfellow’s “Paul Revere’s Ride”—Captain Pulling climbed all eight stories to the top in order to hang the two lanterns that would announce the Red Coats’ approach from the sea, toward the banks of the Charles River.
What do you love about your hometown history?
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