Traveling Through Time on Boston’s Freedom Trail

Boston's Freedom Trail

Traveling through time on Boston’s Freedom Trail is as simple as following the red brick sidewalk for 2.5 miles. Hashtag #HistoryHappened. Let’s face it: Boston was the epicenter of our fight with the British crown and red coats before the Continental Congress signed the Declaration of Independence in 1776.

Freedom Trail

So I have to say that the #1 thing to see is Boston’s Freedom Trail. And the only true way to experience it is through a guided walking tour. I had hurriedly booked a morning tour with Free Tour by Foot after I arrived in Boston. But I didn’t get a confirmation so I had to pay for a walking tour ($16). It was worth it. I booked it on-site at the Boston Common Visitor Center at 139 Tremont Street in Boston. There was only a 20-minute wait.

The famous Freedom Trail is a 2.5-mile red-brick trail through Boston’s historic neighborhoods that tells the story of the American Revolution.

To say our guide was good is an insult. He was a Thespian who entertained us with jokes, gossip, and fascinating facts about Boston’s Revolutionary heroes for 90 minutes. Since Boston was broiling during a weird spring heatwave, he skipped his wool Patriot’s costume for a red shirt and black pants. His red beard coordinated nicely with his outfit. (I am also grateful that he consistently steered our large group under trees whenever possible.)

I would have a hard time choosing between my favorite site on our tour because we saw a unique collection of museums, churches, meeting houses, burying ground, and parks.

“Every step tells a story.”

Boston Common

The definition of “common” is pertaining or belonging equally to an entire community, nation or culture. This certainly applies to the community of Boston, lovers of baked beans and their beloved Red Sox.

Boston Common is America’s oldest public park. It was created in 1634. Massachusetts colonists purchased the 44-acre lot from Anglican minister William Blackstone. The lush green lawn rolls out like a carpet. Bring a picnic basket and a blanket to enjoy a meal in the shade of a centuries-old oak or elm tree. (Or as in the nation’s capital, find a spot on the grounds of the U.S. Capitol and relax for a while.)

Massachusetts State House

Gleaming in the sun, the gold-topped roof of the Massachusetts State House (24 Beacon Street) looks like a mirage. Architect Charles Bullfinch designed it. Since its opening in 1798, the building has served as the seat of state government. (We learned it is adjacent to the former site of the historic Hancock mansion.)

You can take a virtual tour of the state capitol through a State House Time Capsule DVD preview on YouTube.

Due to the pandemic, the state House is currently closed to the public until further notice.

Park Street House

As a Puritan stronghold in New England, Boston is home to a lot of churches. You could spend a morning just touring old churches in the city. We saw the Park Street Church on our walk, which was built in 1809. Its 217-foot steeple was so tall that it was the first thing visitors saw when traveling to Boston. It is situated corner of Park and Tremont streets.

Granary Burying Grounds

Ok I call it a cemetery, but Bostonians christened this historic venue as burying grounds. Undoubtedly my favorite site on the entire tour, this cemetery has oh so many stories to tell if the dead could talk. Built in 1660, it is the final resting home to many of America’s most famous Revolutionary heroes. There are 2,345 markers at this cemetery.

The Who’s Who of this cemetery include the graves of three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine; Peter Faneuil, benefactor of the famed downtown Boston landmark; patriot and craftsman Paul Revere; James Otis, Revolutionary orator and lawyer; and five victims of the Boston Massacre.

You’ll even discover a 25-foot-tall obelisk that commemorates the tomb of Benjamin Franklin’s parents.

(Interesting fact: The burying grounds is named after the 12,000-bushel grain storage that operated next to this property.)

Paul Revere’s Tomb

While learning about Paul Revere’s midnight ride is obligatory for any elementary school history class, there is so much more that I didn’t know about this patriot—silversmith and copper plate engraver. There is also a story (?myth?) that he made wooden dentures for George Washington.

But I guess he will always be best remembered as the hero of Henry Wadsworth Longfellow’s epic poem (Paul Revere’s Ride). He alerted residents in the colony on April 18, 1775 that the British were attacking.

“Listen, my children, and you shall hear / Of the midnight ride of Paul Revere . . .”

Henry Wadsworth Longfellow

The poem was published in 1861 as the nation was embroiled in The Civil War.

Samuel Adams’ Tomb

So we all know that patriot Sam Adams was the cantankerous cousin to John Adams. He also brewed beers right? Well, he inherited his father’s brewery. But the Sam Adams Boston lager beer is named after the patriot and founding father. You can tour the Boston Beer Company, which is located in Beantown.

Old Corner Book Store

I didn’t take a photo of the Chipotle Mexican Grill restaurant chain that now occupies this prime real estate (because who hasn’t seen this site on any city street in Anywhere, USA?), BUT it is one of the places we saw on the Freedom Trail. (I wish I had pulled out my iPhone.) Located at 283 Washington Street, it was the home of Ticknor and Fields. This 19th-century book company published such 19th-century “greats” as Henry David Thoreau’s Walden and Hawthorne’s The Scarlet Letter.

Old South Meeting House

I think my favorite part of my visit to Boston was standing at an intersection looking back at the Old South Meeting House. I literally felt like I had one foot in the past and the other foot in the present. Highrise buildings loom around this Boston landmark. Our guide told us this building was saved from the wrecking ball by 20 women of Boston in 1876. Today the South Meeting House is a museum.

Old State House

This majestic building (206 Washington Street) stands as tall as an oak. The building precedes the Continental Congress, the Declaration of Independence, and the Revolutionary War.

Boston's Freedom Trail

Built in 1713, it is the oldest surviving public building in Boston. The Old State House represented the heart of colonial Boston’s political and civil life. The Boston Massacre occurred on March 5, 1770 on these hallowed grounds.

“It became a point of origin for vital debates about self-government that sparked the Revolution.”

Revolutionary Spaces

Boston Cream Pie

Clearly not an item to be reported in a history book (but obviously important to any dessert lover) is the history of the city’s famed Boston Cream Pie. We learned that the Omni Parker House is credited with the invention of the Parker Roll. But the hotel also earns credit for inventing the cake pudding dessert.

Originally dubbed “Parker House Chocolate Cream Pie,” Boston Cream Pie became an immediate and perennial hit.

Omni Hotels

On December 12, 1996, the Boston Cream Pie was proclaimed the official Massachusetts State Dessert thanks to a local high school civics class that sponsored the bill. Sweet!

Home of Boston Cream Pie

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    July 31, 2021 at 1:11 am

    Boston cream pie sounds yummy. I would love to try that one day.

    • Terri
      August 1, 2021 at 9:09 am

      I cannot begin to describe how delicious it is – custard, cake and dark chocolate icing. HEAVEN!

  • sue
    July 31, 2021 at 4:17 am

    This looks like a fantastic walk & like you, I always seem to find cemeteries so fascinating so have no doubt that this would be my highlight too…& the cream pie. I would also enjoy the cream pie 😉

    • Terri
      August 1, 2021 at 9:06 am

      I love visiting cemeteries too when I visit a city. It is really great when they offer walking tours so you learn about the “residents”!

  • Alma
    July 31, 2021 at 5:07 am

    Love walking through cities and exploring and the Freedom Trail is a great way to learn about the history of Boston. A great article. What better way to end off a day of exploring than ending off with an official Massachusetts State Dessert!

    • Terri
      August 1, 2021 at 9:08 am

      I absolutely agree Alma. Walking is the best way to explore a city. You really get to stop and notice things. And no trip to Boston is complete without eating a Boston Cream Pie.

  • Tish
    July 31, 2021 at 9:50 am

    Love this article and yummy pie!!
    Boston is one of my favorite places to visit

    • Terri
      August 1, 2021 at 9:07 am

      I love Boston Cream Pie too, Tish. DELISH!

  • Anja
    August 1, 2021 at 5:58 am

    That cream pie house looks like a fancy hotel! I have never been to Boston but love the pictures, the combination of very historical and modern. Will be a while yet but when we can travel to the US again, I would love to visit Boston. Saved for future reference. Great post!

    • Terri
      August 1, 2021 at 9:07 am

      Boston is a must see city if you travel to the US again. I love it. It’s a very walkable city. In the Omni is one of Boston’s famous hotels!

  • Alaine
    August 1, 2021 at 2:04 pm

    I remember the couple trips to Boston and walking through Boston commons. The most memorable trip was with my family, my Father went to university in Boston and had an apartment on Newbury street. Surreal for him to see his old apartment building still there even though the street is completely different nowadays

    • Terri
      August 7, 2021 at 2:25 pm

      What a cool experience. I sometimes go back to where I grew up outside Washington DC and I hardly recognize the city. It changes so much yet holds so many memories.

  • Rachel-Jean Firchau
    August 1, 2021 at 2:24 pm

    super thorough guide! i checked most of these places out during my trip to Boston in 2019, but i can’t believe I didn’t get any boston cream pie!

    • Terri
      August 7, 2021 at 2:24 pm

      You missed a treat Rachel-Jean. Definitely get this dessert next visit to Boston.

  • Shelby Lamb
    August 2, 2021 at 10:42 pm

    Boston cream pies are one of our favorite desserts! The entire Freedom trail looks pretty amazing though! Anything historical is always incredible!

    • Terri
      August 7, 2021 at 2:25 pm

      Mine too! Who can resist dark chocolate, custard and buttery cake??? Boston is a great city to visit for history buffs.

  • tiffy roxxx
    August 7, 2021 at 10:33 am

    Loved this! As a history lover, there’s so much in Boston, I need to stop by!

    • Terri
      August 7, 2021 at 2:22 pm

      BOSTON is awesome. There is so much to do in BeanTown.