Walking Boston’s Freedom Trail

It’s a cool, sunlit morning in Boston, one of those picture-perfect days you hope for when exploring a city. I pass the flower-studded site of the Boston Marathon bombing — a sobering reminder of what happened here earlier this year.

Boston is one of my favorite cities and although I’ve been many times, it always calls me back. I love tracing the footsteps of the patriots who walked here; while the city was obviously so different 300 years ago, their energy seems to linger around every corner. This is the “Cradle of Liberty,” the birthplace of American Independence and I’m anxious to embrace the milestones. What better place to start than where it all happened, along the Freedom Trail.

In Your Bucket Because…

  • Everyone loves Boston.
  • Boston is more than just about baked beans and Red Sox.
  • Good for families, lovers of history, sightseers.

Started in the 1950s by concerned Bostonians who wanted to preserve the story of the American Revolution, the 2.5 mile trail is marked by a bricked or painted red line which winds past 16 historically significant sites, starting at Boston Common and ending in Charlestown at the USS Constitution. Today the Freedom Trail is an integral part of Boston, attracting more than 3.2 million visitors annually.

Boston's venerable State House

Boston’s venerable State House (photo: Michelle Richmond)

Setting the Stage

The Freedom Trail Foundation offers guided tours, led by docents in period garb who transport you to another era while blending history with colorful anecdotes along the way. If you prefer a “do-it-yourself” experience, you can purchase the recently debuted three-and-a-half hour MP3 audio guide for $17 or download a mobile app on your Smart phone.

I opt for the personal touch as Henry Wadsworth Longfellow’s poem unexpectedly pops into my head:

“Listen my children and you shall hear of the midnight ride of Paul Revere …..” as I set off for Boston Common.

"George Wright" Boston Freedom Trail Guide

“George Wright” Boston Freedom Trail Guide (photo: Michelle Richmond)


“Hi, my name is Michael,” our guide, clad in period dress, announces to our small group. “Would you like me to slip into character or shall I stick with modern-day talk?”

We all want the “real” deal.

“In that case, my name is George Wright,” he says, slipping into a full British brogue. “I was born here on Nov. 18, 1745 and I’m a cabinetmaker. We’re standing on Beacon Hill and if you look over there, that was the site of the first gallows. As you can see, it’s now part of a kids’ playground. Bet you didn’t except that, did you?”

“George” appears to be a comedian.

“Our tour begins at the State Capitol and ends across the river in Charlestown, but I’ll be with you only for the first mile of this journey. After that, you’re on your own to explore the rest of the city.”

After wrestling to adjust his waistcoat and suspenders, George leads us to the State Capitol, stopping in front of the Robert Gould Shaw monument, located across from it. The intricately carved bronze relief is dedicated to the 54th Regimen of the Civil War.

“Look closely at the details on the soldiers’ faces,” he instructs. “What do you see? Look above at the woman flying above them. Do you see the angel of death, or is she protecting them?”

We then look across to the “new” State House – completed in 1798.

“This was designed by Charles Bulfinch and the golden dome was once made of wood and later overlaid with copper by Paul Revere,” George relates.

Passing by Park Street Church we find a crowd of tourists listening in rapt attention to their guide, who is regaling them with stories about “Brimstone Corner,” as it was known because of the gunpowder stored in its crypt during the War of 1812.

Underground “Glitterati”

Our next stop, Granary Burying Ground — the third oldest burying ground in Boston — is the final resting place of Benjamin Franklin’s parents (Ben is buried in Philadelphia, where he lived most of his adult life), Paul Revere, John Hancock and “Mother Goose,” among others.

Paul Revere's original headstone

Paul Revere’s original headstone (photo: Michelle Richmond)

George spends quite a bit of time here, giving you a sense that it’s a favorite site.

“Now, how many people do you think are actually buried here?” he quizzes.

We mutter some numbers, falling woefully short of reality.

“There are only 2,300 markers here, but it’s thought that more than 5,000 people are underground,” he informs us. To save space, some were buried standing up and nobody’s really buried where their markers say they are. If you notice, they’re all in neat rows. Why do you suppose that is?”

Paul Revere monument

Paul Revere monument (photo: Michelle Richmond)

Someone in our group correctly guesses that they were moved to facilitate maintenance.

“That’s right! They were moved so that the grass could be mowed more easily.”

He tosses out more anecdotes before ushering us past King’s Chapel and Burying Ground (the city’s oldest), stopping at Ben Franklin’s statue and Boston Latin School (the oldest public school in the US).

Across the street, the Omni Parker House Hotel has operated as a hotel since 1855.

“That’s where the Boston cream pie was invented,” George tells us. “John Wilkes Booth was a guest here and they say that he was seen target practicing down that alley alongside it, just days before he went to Washington D.C. We all know what happened when he got there.”

Cradle of Liberty

Quincy Market

Quincy Market (photo: Michelle Richmond)

We continue towards Fanueil Hall, site of America’s first Town Meeting, stopping for a solemn moment in front of Old State House, site of the Boston Massacre in which British soldiers killed five civilians in 1770 and injured six others.

“What happened here was an accident. The soldiers fired on the crowd without orders to do so,” George tells us.

Erected in 1713, this was the Capitol of the colony and is the oldest public building still standing in the eastern US. “The Declaration of Independence was read from that balcony,” says George.

At our next stop George bids us farewell. “This is where I get off. If you walk for 10 minutes in that direction, you’ll arrive at Paul Revere’s House,” he says pointing northeast. He tosses out a few more anecdotes before tapping his three-corner hat and heads off.

Faneuil Hall, given to Boston by Peter Faneuil, “the topmost merchant in all the town,” in 1742 is topped off by a weathervane with a copper and gold leaf grasshopper, crafted by Sherm Drowne. During the War of 1812, according to legend, it was used to screen spies, for: “Anyone who claims to be a Bostonian and who does not know the shape of Fanueil Hall’s weathervane must be an impostor.”

Today, the venerable hall and the surrounding complex known as Quincy Market is a marketplace brimming with vendors and restaurants. Quincy Market Colonnade is the largest food hall in New England.

I still have a mile-and-a-half of Freedom Trail to walk so I stop to fortify myself with a mouth-watering lobster roll before heading off in the direction of Paul Revere’s House, Old North Church, Copp’s Burying Ground, the USS Constitution (“Old Ironsides”) and the Bunker Hill Monument.

Somehow, it just won’t be the same without “olde George Wright” leading the way.


The Freedom Trail Foundation offers guided tours daily throughout the year. There are 12 daily tours April – Nov. and a reduced schedule Dec. – March. Tickets are valid for any day, for any tour time and may be purchased online or at the departure location. Tours are limited to 10 people.

Tours leave every hour on the hour (beginning 11:00 a.m.) from Boston Common Visitor Information Center and every hour on the half-hour beginning 10:30 a.m.) from Arts Boston BosTix booth at Faneuil Hall. Tours are $12 for adults, $8 children 6 – 12.

Available on all platforms, the new Freedom Trail® mobile app features 16 official historic sites of Boston’s Freedom Trail. The app is offered on iTunes for $4.95. The recently introduced three-and-a-half hour MP3 audio guide can be purchased for $17.

Average rating for this trip


  1. Blanche says

    Hi there, I would just like to comment on what a great piece this was! I actually lived in Boston for four years (this is going back) and am embarrassed to say that I learned more from this article than I did living in Boston for four years. What a cool way not only to explore the city, but to get a history lesson in too. Thank you so much for opening up my eyes to such a neat experience!

  2. Diane Lizza Sanders says

    What a fabulous article! The writer makes you feel like you are there in person taking the guided tour yourself. This truly makes me want to get to Boston as soon as possible. However, I would think the Fall would truly make for a wonderful experience with y’alls fall foliage and all.

  3. Susan Gilbert says

    Great piece! I love history, and this article makes me want to book a trip to Boston and walk the trail. So much wonderful information! I would love to read more articles by this author regarding more interesting places to visit.

  4. Tom M says

    Enjoyed reading this article for its “one foot in the past-one foot in the present” approach to exploring this facet of Boston. Love history that I can “connect’ to, and reading this gave me that kind of experience. On July 3rd visited the Old North Bridge in Concord and Lexington Green. After reading this, now wish we had started at the Freedom Trail’s beginning and later proceeded to Concord and Lexington .

  5. Cynthia Cassidy says

    What a wonderful piece! The author made it both insightful and informative. This is the type of travel writing that really encourages you to GO DO IT! Kudos

  6. Iris says

    Great read! The writer did an excellent job of providing plenty of practical information while inspiring the traveler with her clever descriptions. Although I’ve had the pleasure of visiting Boston before, this article made me wish I could go back and discover its hidden gems.

  7. Jackie Bridgman says

    I have never been to Boston but after reading this wonderful article I will definitively plan a visit to such a great city with so much history.
    All the information included in the article will make my planning and visit a lot easier.
    Thank you Michele for a great article, I hope you will write again soon on another city.


Leave a Comment