Boston’s Freedom Trail
By Holly Bowne10 guided tours through history with someone who’s been there before
Take a walk through history. In 1630, Puritan colonists from England founded what became the town of Boston, the epicenter of our nation’s birth. Today, you can trace Boston’s captivating past by exploring the celebrated Freedom Trail®. The 2.5-mile red-lined path winds through the city and along cobblestone streets to 16 well-preserved historic sites that together tell the story of America’s fight for independence and the subsequent shaping of a nation. Some examples include the Massachusetts State House, the Site of the Boston Massacre, Paul Revere’s House, the USS Constitution, and the Bunker Hill Monument.
Explore the trail on your own or choose from one of the guided walking tours. Knowledgeable guides dressed in full 18th-century garb lead all the Freedom Trail Foundation tours. Far more entertaining than any dry history book, the guides are master storytellers. They regale you with insider tales of intrigue and high treason, mob agitations and lesser-known secrets, making you feel as if you’re actually living during the days of the Revolution. Whether you’re an avid history buff or hoping to bring history to life for your kids, there are options a-plenty.
1. Walk Into History® Tour
Through 11 Freedom Trail sites, learn about the brave patriots who dared to challenge the strongest power of the 18th century. Hear echoes of orators such as Samuel Adams. Envision the blood on the snow outside the Old State House on the night of the Boston Massacre, and witness the balcony where the Declaration of Independence was first read aloud in 1776.
Insider Tip: Tour attendance is usually lighter later in the day.
Length: 90 minutes
Distance: 1 mile
Operates daily
2. North End Tour
Experience an in-depth exploration of eight sites on the Freedom Trail’s northern end. Visit Faneuil Hall, Paul Revere’s House, Old North Church, and other key spots in Boston’s oldest neighborhood.
Insider Tip: Look for British bullet holes peppering Captain Daniel Malcolm’s tombstone in Copp’s Hill Burying Ground.
Length: 90 minutes
Distance: 0.8 mile
Operates daily
3. Historic Pub Crawl
Boston’s earliest patriots brewed some of their best plots against the Redcoats over pints of ale in their favorite watering holes. Trace the bar stools of the Sons of Liberty as you discover the “true” birthplace of the country during a good old-fashioned pub crawl. This adults-only tour takes you to seven sites, including four historic taverns, where you’ll sample brews and contemporary Boston fare. Raise your glass in the Green Dragon Tavern, where Paul Revere overheard plans for the invasion of Lexington and Concord. Visit the Bell in Hand Tavern, America’s oldest continuously operating tavern. And savor award-winning clam chowder in the Union Oyster House, Boston’s oldest restaurant.
Insider Tip: On the third Monday in April, witness the battles of Lexington and Concord at the annual Massachusetts Patriots’ Day Reenactment.
Length: 90 minutes
Distance: .25 mile
Operates Tuesdays at 5:30 p.m.
4. African-American Patriots Tour
Discover the bravery, risk, and defiance of African-American Bostonians who played vital roles in the American Revolution and the formation of the United States. Learn about revolutionaries such as Crispus Attucks, the first victim of the Boston Massacre, the first African-American female poet, Phillis Wheatley, abolitionist Prince Hall, soldier Peter Salem, and more. This educational tour takes you to 10 historic sites, including the Abiel Smith School, the nation’s oldest public school built for the sole purpose of educating African-American children.
Cool Fact: Phillis Wheatley was personally invited to visit George Washington to read the poem she wrote about him.
Length: 90 minutes
Distance: 1 mile
Operates February
5. Revolutionary Women Tour
Abigail Adams urged her husband, John Adams, to “remember the ladies… we are determined to foment a rebellion” if ignored. This tour covers 11 Freedom Trail sites, exploring four centuries of Revolutionary women who changed history, fought for equality, and helped shape America. Women such as Mary Dyer, who was hanged from an elm tree for her outspoken religious beliefs, Lydia Maria Child, an abolitionist, Susan B. Anthony, a women’s rights activist, and abolitionist Sojourner Truth, the first African-American woman to win a court case against a white man.
Cool Fact: The 19th Amendment, which gave women the right to vote, was called the Susan B. Anthony Amendment.
Length: 90 minutes
Distance: 1 mile
Operates March
6. Pirates & Patriots® Tour
Arrrggh! Wind your way through the back streets and narrow alleys of Boston’s historic harbor area. Hear entertaining accounts of the legal and illegal adventures of pirates and privateers, jack tars (sailors) and landlubbers. Visit seven sites while learning about the unique struggles of the people who lived and worked in America’s largest port city.
Cool Fact: George Washington hired privateers and legalized acts of piracy against the British Navy.
Length: 90 minutes
Distance: 1.25 miles
Operates July to August
7. Lantern Tour
Under the cover of darkness, investigate a chilling side of Boston’s past. Visit seven Freedom Trail sites while your guide shares spellbinding tales too macabre for daytime—spies and assassins, fatal sword duels, cold-blooded murders, the punishment and hanging of convicted witches. True accounts are brought to life as you delve into dark histories and mysteries of the Freedom Trail.
Insider Tip: While open to anyone, the tour is recommended for ages 12 and up.
Length: 90 minutes
Distance: 1 mile
Operates September to October
8. Historic Holiday Stroll
Feel like characters in A Christmas Carol when you immerse yourself in a nostalgic Christmas-time tour. Your 19th-century Dickensian guide takes you to nine historic sites, sharing how Boston’s holiday traditions evolved. After the tour, warm yourself with hot chocolate, tea, or wine, and slices of Omni Parker House’s famous Boston cream pie.
Insider Tip: Tour participants are entered to win a complimentary brunch for two at award-winning Parker’s Restaurant at the Omni Parker House.
Length: 90 minutes
Distance: 1 mile
Operates November to January
9. Boston Harbor USS Constitution Cruise
A 45-minute narrated cruise on Boston Harbor floats you up-close and personal with one of Boston’s most treasured landmarks, “Old Ironsides,” formally known as the USS Constitution. Still officially commissioned, the wooden-hulled frigate was originally launched in 1797 and played a pivotal role in the War of 1812. You can disembark at the Charlestown Navy Yard to tour the famous ship, as well as the USS Cassin Young and USS Constitution Museum.
Insider Tip: The USS Constitution is closed on Mondays.
Length: 45 minutes
Operates March to November
10. Old North Church Behind-the-Scenes Tour
Climb the narrow staircase to the steeple room where a teenage Paul Revere worked as a bell ringer, and view the oldest set of change-ringing bells in North America. Walk among the 37 tombs inside the crypt while viewing artifacts and learning about the church’s architecture and fascinating history.
Insider Tip: If you have a sweet tooth, don’t miss Captain Jackson’s Historic Chocolate Shop right next door.
Length: 30 minutes
Operates daily
Good luck in narrowing down which tours to take… (fortunately, there’s no limit).
