Boston Freedom Trail and Tea Party Ships & Museum

Our two favorite excursions in Boston were the Freedom Trail tour and the Boston Tea Party Ships and Museum. The Freedom Trail tour takes you on a two and a half mile jaunt around Boston, stopping at 16 nationally significant historic sites. The tour is commonly referred to as following the “red line,” a literal red line that navigates you through all these important stops in Boston. The Freedom Trail was preserved and dedicated in 1951 and affords you an opportunity to see and experience Boston’s unique history from meeting houses, to churches, to burying grounds.

The best part of the tour is your guide – the Freedom Trail tour doesn’t just hand you a boring historian to lecture you on American history; they give you an experienced and trained professional, complete with historically accurate 18th century clothing and a mind-bending knowledge of history. They play a key and iconic figure in Boston’s early history, conducting the entire tour in character. The character they represent comes to life right before your eyes – and they never break character, so don’t ask. Don and I had the wonderful pleasure of having John Singleton Copley lead our tour.


John Singleton Copley was a Bostonian painter in the late 1700’s, famous primarily for his striking portraits of Boston’s notable population, including Paul Revere, Thomas Gage, and John Hancock. Dear Mr. Copley isn’t the only important figure you might meet on the Freedom Trail – groups are also led by John Hancock, Abigail Adams, and Samuel Adams, to name a few. The Freedom Trail tours offer a variety of choices, the most popular being the “Walk Into History” tour, led daily at 11am, noon, and 1pm. It starts off at the Boston Commons at 139 Tremont Street.

The Freedom Trail offers other amazing tours as well, depending upon what you are interested in. Check out the “Historic Holiday Stroll,” offered November through December on select weekends, the “Historic Pub Crawl Private Tour,” given upon reservation, the “African-American Patriots” tour, scheduled on Saturdays and Sundays during Black History Month in February, the “Revolutionary Women” tour, scheduled on weekends in March, the “Pirates and Patriots” tour, offered on weekends in July and August, and the “Lantern” tour, offered in select weekends September through October. Check out the “North End” tour and the “Reverse Walk Into History” tour, both returning in Spring of 2020.

Don and I elected to do the “Walk Into History” tour, which, like I said, starts in Boston Common. Boston Common is America’s oldest public park, established in 1634. The park is steeped in history; this is the park where the Colonial militia prepared for battle, where victory gardens were grown during World War I, and where Charles Lindbergh first began to excite the public about commercial aviation. Today, the park offers expansive, relaxing areas of lawn, beautiful trees and fountains, and Frog Pond – a skating rink in winter and a mini water park in summer. The tour also takes you past the Massachusetts State House.





One of the first stops was also one of the coolest – the Granary Burying Ground on Tremont Street. It is Boston’s third-oldest cemetery, established in 1660. It is best known as the burying site for many historically influential people including Samuel Adams, John Hancock, and Paul Revere.




John Hancock Memorial



As we meandered along, we stopped at Boston’s Old City Hall, home to Boston’s first public school with such famous pupils as Ben Franklin, John Hancock, and Samuel Adams. Today, the Hall is made up of office and retail space while still capturing its old charm and historical influence.


Don’s favorite part of the Old City Hall was, of course, the bronze donkey. What is a donkey statue doing on the property of such a historical site, you ask? Don will tell you. In 1966, the Architectural Heritage Foundation was founded by a man named Roger Webb. In part, Mr. Webb established this foundation to save Boston’s Old City Hall, which was slated for demolition. Fast forward thirty-ish years – Mr. Webb finds himself in a Florence, Italy art store perusing the statue collection. Sitting behind a replica of Michelangelo’s David, Mr. Webb found a bronze statute of a donkey priced at $10,000. For some reason, Mr. Webb fell in love with it and had it shipped to Boston with the intent of placing it on the Freedom Trail to serve as a quasi jungle gym for children being drug along the boring historical Freedom Trail tour.

Story goes that Boston lost its collective mind, convinced that a random donkey statute had no place on the Freedom Trail. Mr. Webb met them halfway and agreed to put the donkey on the property of the Old City Hall, which he owned through the Architectural Heritage Foundation. He (somewhat disingenuously) told Boston that the donkey had a legitimate place on such a historical site because it represented the Democratic Party. Naturally, once the donkey was placed, people began to ask where the Republican elephant was going to go. In response, Mr. Webb had a sculptor place two footprints in front of the donkey for those opposed to the Democratic Party to stand in opposition to it.



After checking out the donkey, we took a break at the Old South Meeting House, located on the corner of Milk St. and Washington St. It began as a church, built in 1729, and later evolved into more of a public space for meetings, speeches, and political organization. Debates surrounding British taxation policies occurred at the Old South Meeting House, as well as famous speeches by John Hancock. The lively discussions around the tax issue led to the formation of the Boston Tea Party on December 16, 1773 who eventually tossed an entire shipment of tea into the Boston Harbor.

Another cool spot on the tour is the Old State House, which was the seat of the Colonial government from 1713 to 1776. It is more famous as the site of the Boston Massacre, which occurred on March 5, 1770. This altercation between British soldiers and colonists is commemorated by a cobblestone commemoration in the square below the Old State House balcony.



Probably our second favorite Boston jaunt was the Boston Tea Party Ships & Museum, on 306 Congress Street. It is open from 10am to 5pm April 1 – October 31, and 10am to 4pm November 1 – March 31. Touted as the “#1 Best Patriot Attraction,” the Boston Tea Party Ships & Museum is a fully guided tour with live actors, interactive exhibits, and  full-scale replica 18th century sailing vessels. You can even “throw tea” into the harbor!

The museum experience is one of the best I’ve had – you start off in the “Meeting House,” where you play along as a Bostonian in 1773, undoubtedly angry about the King’s ridiculous taxes. Each person gets assigned a real individual who was present during this historical event. On Thursday, December 16, 1773, thousands of Bostonians met at the Old South Meeting House to discuss what to do with incoming shipments of tea from England. The Colonists wanted to protest England’s tea tax, but wanted to do so legally and honestly. To that end, they agreed to request a pass for the ships with tea to return to England unloaded. When this was denied, they decided in the Meeting House to take action. How do you unload and yet not unload a ship in Boston? You throw the cargo in the harbor.

Don was William Pierce

The tour moves on to the Tea Party Ships – your group boards a replica of the Beaver, which was, along with the Eleanor, one of the ships carrying the tea into Boston Harbor. You are treated to a really neat tour of the ship.




After the tour of the ship, you get to throw tea into the harbor. Well, kind of. By “tea,” we mean a fake case of tea (the real ones were impossibly heavy), and by “throw,” we mean the fake tea is attached to a rope which you are required to use to return the fake tea to the boat. It’s still pretty fun. Don got into it and, of course, made a friend.



After disembarking, you get to see a reenactment of the political debates and issues that were brewing at the time. As the website describes, you get to “witness” a typical conversation between a Patriot and a Loyalist following the politically scandalous Boston Tea Party.

At this point, you meander into one of the neatest parts of the tour – the Robinson Tea Chest. This thing is real. It is the only known surviving tea chest from the Boston Tea Party. The chest sits in a glass case on a pedestal – while you can’t touch it, you get a really awesome view of all sides of it. The chest itself was crafted in China and eventually used to ship tea to Boston. It has been passed down from generations since then; you can see the drawings and etchings of different parts of the chest’s life on its sides. If that’s not cool enough for you, check out the vial of real tea, just below the tea chest.



At some point, the room you are in comes alive! On the wall are color painted portraits of major figures during the time of the Boston Tea Party – many of them you will recognize. The figures on the paintings abruptly turn into moving images and tell you about their role in the political and cultural changes happening in Colonial America.



Don then insisted on going to Abigail’s Tea Room (shouldn’t be missed). It’s a very cute little shop with a small deli, tons of tasty teas, and a restaurant. Don made friends with the lovely lady selling tea. Of course he did.


Of all the places we have been, Boston was definitely a highlight and shouldn’t be missed. Happy Boston travels!

One thought to “Boston Freedom Trail and Tea Party Ships & Museum”

  1. Great information, Allison. Sounds like they have added some tours since we visited Boston. There is so much there to see and experienced.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.