Touring the Freedom Trail in Boston

Touring the Freedom Trail in Boston

Boston's route of historic sites from the American Revolution makes for a surprisingly humorous tour By: Cody Geib
The Freedom Trail Foundation offers daily tours to Boston’s historic sites from the American Revolution. // © 2014 Cody Geib
The Freedom Trail Foundation offers daily tours to Boston’s historic sites from the American Revolution. // © 2014 Cody Geib

The Details

The Freedom Trail Foundation

Most people probably prefer to go straight to their hotel rooms after catching a red-eye, but during my recent trip to Boston, I took a worthwhile detour after my flight from L.A. landed at 8:00 a.m.

As a first-timer in Boston — and with only one day to spend there — I made sure to squeeze in a tour of the city's historic Freedom Trail, the 2.5-mile route through downtown Boston that connects 16 sites tied to American revolutionary history.

After spending the morning with a friend at Boston Common Frog Pond — which freezes over in the winter and provides excellent ice skating —we headed across Boston Common to the Visitor Information Center to begin our tour.

We took the "Walk Into History" tour with the Freedom Trail Foundation, but there are plenty of other organizations that lead tours along the trail. Our guide, Rob Crean, was decked out in full 18th-century garb –– stockings, cloak, three-cornered hat and all.

Crean goes by the name Isaiah Thomas for his tours, borrowing the persona of the American newspaper publisher who gave Massachusetts's first public reading of the Declaration of Independence.

When he's not leading tour groups, Crean doubles as a comedian and standup comedy teacher — which doesn't come as a surprise to anyone who has experienced his tours. From the get-go, he kept our group laughing with his witty take on revolutionary history, such as his summary of the Declaration of Independence as saying, "Dear England, we're splitsville."

After learning about the gold-domed Massachusetts State House, which overlooks Boston Common, our group headed north on the Freedom Trail to Park Street Church and the Granary Burying Ground, where several important figures from the revolution are buried.

Standing along the graveyard's gate and its many headstones, Crean told our group about the people buried there, including John Hancock, the American revolutionary famous for his large signature on the Declaration of Independence. Crean joked about how Hancock forgot to sign his will, leaving it without the necessary "John Hancock." He also added the strange, grisly tale about the grave robbers who couldn't pry the rings from Hancock's body — and just took the famous signing hand with them.

In one of my favorite one-liners from the tour, Crean pointed out the snow-covered tombstone of patriot Samuel Adams, which faces Beantown Pub on the other side of Tremont Street, and noted that the pub is "the only place where you can have a cold Sam Adams while looking at a cold Sam Adams."

The Freedom Trail Foundation recently released its official mobile app, which contains a map of the various sites with pictures and information about each one, as a way to experience the trail. In addition to seeing the historic sites themselves, however, Crean said that the chance to listen to and interact with the guides is what makes the tours special.

"I'm a performer, so I like engaging with people and getting a response from them," Crean said. "I like the fact that I'm doing something that allows me to educate people in a cool and fun way. There are tours that probably have more information than mine, but I play up the performance aspect of it more because I think you retain the information better if it's delivered in an entertaining way."

Having grown up near Boston, Crean said that he already had a good understanding of the local history. When he began as a tour guide, he read books and watched other people's tours to learn even more about the history of the revolution in New England. Once they master the information, guides are then free to shape their tours however they like — as long as they include the necessary stops.

"Everybody's tour is different," Crean said. "All the tour guides come up with their own tours, and everyone talks about what they find the most interesting. As long as what we're saying is true, we can say anything we want."

From the Granary Burying Ground, we continued toward the North End to see such sites as King's Chapel, Boston Latin School, the Old South Meeting House and the Old State House, where the Declaration of Independence was read from the balcony to the people of Boston in 1776.

Finally, we finished the tour at Faneuil Hall, home to the meeting hall where colonists first protested the Sugar Act and the Stamp Act and held other historic meetings on the way to revolution.

Before bidding goodbye to the group, Crean encouraged everyone to review his tour online, saying, "If you have enjoyed my tour, my name is Isaiah Thomas. If you have not, my name is Paul Revere."

Using the Freedom Trail app, I continued along the trail to see some sites not covered in the tour, including the Bunker Hill Monument on the other side of the harbor in Charlestown. A tall white spike, the monument resembles the Washington Monument and features a huge spiraling staircase that visitors can ascend to the room at the top for an aerial view of Boston.

As I toured the site, I pulled out the app again to learn more about the historic battle between the redcoats and the colonial militia that occurred there in 1775. As I paused at the base of the monument, appreciating the hill's great significance in American history, I couldn't help but wonder what witty insights "Isaiah Thomas" would have to offer.

After a full day of sightseeing, I also had a keen hankering for a cold Sam Adams — the beverage, that is.

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