Road to Revolution: Top Historical Stops in Boston, MA

Teaming with history at every corner, Boston offers an abundance of significant sites for history buffs. From walking the freedom trail to strolling through historic cemeteries guests are sure to learn something new about America’s roots.

Top 7 Historical Stops in Boston, MA

Discover the must-see Boston historical sites to get the most out of your trip.

Boston Freedom Trail

No trip to Boston would be complete without a stop along the Freedom Trail which connects many significant sites of America’s history along 2.5 miles. The trail features sixteen historic sites starting with the Boston Common to Paul Revere’s house in the North End, including museums, churches, meeting houses, parks, a ship, burying grounds, and historic markers along the way. Each site along the trail tells its very own story surrounding the American Revolution and beyond.

Bunker Hill Monument

The Bunker Hill Monument, located along the Freedom Trail in Charlestown is integral to the American Revolution, this granite monument was built to commemorate the Battle of Bunker Hill (1775) the very first major battle of the Revolutionary War.

Today, it is home to the Bunker Hill Museum where visitors can view dioramas, murals, and artifacts from the battle including a cannonball, a sword, and a snare drum, among many other items.

Visit the monument on our Best of Boston Tours, featuring stops at the USS Constitution, Bunker Hill Monument, a narrated drive, and a Boston harbor cruise! 

Tripshepherd Fun Fact: the Bunker Hill Monument, standing at 67 m, was the tallest memorial prior to the Washington Monument!

Paul Revere House

Another important stop along the Boston Freedom Trail is the Paul Revere House, the house where the infamous American patriot, craftsman, businessman, and entrepreneur Paul Revere lived and where his 20-mile journey was known as the Midnight Run.

After serving many years as the location for many shops and housing various businesses Revere’s great-grandson purchased the building in 1902 and restored it so it could be open to the public, opening its doors in 1908 as one of the earliest historic house museums in the United States.

Visit the Paul Revere House illuminated at night with our Scenic Boston Night Tour.

USS Constitution.

Included in our new Boston City Tour, is the world’s oldest commissioned warship afloat - the USS Constitution, also known as “Old Ironsides” located in the former Charlestown Navy Ship Yard. Launched in 1797, this wooden-hulled three-masted heavy frigate was one of the original frigates authorized by the Naval Act of 1794.

The ship was used during the War of 1812 against the United Kingdom defending numerous warships including HMS Guerriere. The ship retired from service in 1881, serving as a receiving ship until 1907, and in 1934 she completed a 3-year, 90-port tour of the nation, celebrating her 200th birthday in 1997.

Today, you can visit the USS Constitution Museum to understand the navy’s role in war and peace through exhibits, daily programs, and historic demonstrations put on by her crew of 60 officers and sailors.

Old North Church, Boston MA

Near the very end of the historic Freedom Trail is the Old North Church, the oldest church in Boston and the site that launched the American Revolution!

Built in 1723, the church is the location from which the “one if by land, two if by sea” signal is said to have been sent. In 1775, Revere told three Boston patriots to watch for British troops and hang two lanterns on the church’s steeple which would serve as a warning for Charlestown patriots about the movements of the British army.

Today, the Old North Church is an active Episcopal Dioceses of Massachusetts congregation where visitors can take a self-guided tour through the church.

Faneuil Hall Marketplace

Faneuil Hall Marketplace also known as “the home of free speech” and the “Cradle of Liberty” was constructed in 1764, built by artist John Smilbert who used English Country Markets as an inspiration. Sitting atop Faneuil Hall is an 80-pound golden grasshopper, the most famous weather vane in the city, designed by Shem Drowne.

During the war of 1812, it is said that in an attempt to spot spies anyone who responded incorrectly to the question: What is on the top of Faneuil Hall? It would be considered suspicious. The Hall since has been the setting for 300-500 new citizens swearing-in, in and taking the Oath of Allegiance inside the Great Hall.