5 Voices from New England’s Quintessential Historic Walking Tours

The job of a Boston Freedom Trail interpreter isn’t for the faint of heart. Encompassing 16 nationally significant sites in an hour and a half, the tours can’t just be a dry history lesson. The work clothes—aka colonial costumes—are a complicated affair. And when tour groups can number nearly 100 at a time, expert guidance through Boston’s creative traffic patterns is essential.

Here are five who have answered the call.

1. Chris Joazard

AGE: 25 | FROM: Brockton, MA | YEARS ON THE JOB: 6 | PORTRAYS: Crispus Attucks, the first person killed in the Boston Massacre

“The minute I put on the costume and walk outside, I feel like I’m representing the city. When you’re wearing regular clothes people don’t notice you, but when you’re in this outfit people see you. And I embrace that, because when tourists come to Boston, they’re looking for that colonial history. I wave, I smile, I strut down the street. I walk around like I own the clothes, like I’m going out to a nice party.”

Josh Rudy

AGE: 49 |  FROM: Randolph, MA | YEARS ON THE JOB: 13 | PORTRAYS: Captain Daniel Malcolm, merchant and smuggler

“Your audience’s knowledge of American history really varies. Sometimes people know nothing. Others know quite a bit. But most fall in between, where things are fuzzy. Maybe they remember something about the Stamp Act or something called the Boston Massacre, but it’s all not connected. That’s what the tours do: They make those connections and give the events context. This event leads to the next event, and then what you get is revolution. History begins to click into place.”

Emily Pollock

AGE: 24 | FROM: Arlington, MA | YEARS ON THE JOB: 2 | PORTRAYS: Mercy Otis Warren, writer and historian

“Boston is unique because its historic sites and the modern day are really close together, and even integrated. One of my favorite tour stops is the Old Corner Bookstore, which is now home to a Chipotle. People don’t like to see that, but I’m like, No, this is what makes Boston special: It’s a city that people live in and it’s always changing. People have been building upon the past for hundreds of years…and I think that makes the history feel more relevant.”

John Paul Rivera

AGE: 40 | FROM: South Boston, MA | YEARS ON THE JOB: 7 | PORTRAYS: Henry Knox, Revolutionary War captain

“I’m, like, a fat guy and Knox was a historical fat guy, and so I commiserate with him that way. I can also say it’s the best job I’ve ever had. I’m outside, leading people around Boston, and I’m meeting folks from all around the world. It gives me a chance to learn about where they come from and what their cultures are like, and to see Boston through their eyes. That’s really special.”

Kelli Strong

AGE: 42 | FROM: Dorchester, MA | YEARS ON THE JOB: 7 | PORTRAYS: Phillis Wheatley, poet

“My favorite spot to point out on the tour? It’s actually the monument to Chevalier de Saint-Sauveur [a high-ranking French officer killed in a Boston riot in 1778]. City leaders had promised to build one but didn’t until the French ambassador comes in 1916 and asks to see it. They say, ‘Yeah, yeah, no problem—come back tomorrow.’ And they throw this thing up overnight. The cement is still wet when the ambassador is there, but everyone is like, Better late than never.”