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Becoming a Freedom Trail Player

“Auditioning?” A guy with a wheat-straw ponytail and a British red coat boards the elevator behind me. I turn the tables–he is the enemy, after all–by asking, “What’s a Brit like you doing in a place like this?” The Redcoat takes the bait: “A Brit in the 18th century is a lot like an American in the 21st century,” he responds cryptically. Simultaneously we shout out the punch line: “Broke!”

With the ice-breaking laugh, I learn that Michael Szkolka is a history professor who moonlights on the Trail. His motivation isn’t just to supplement his income. Players make $75 per 90-minute tour (not counting tips), and some players do three or four tours a day in the high season, spring through fall. “You’ve got to have a real love of American history to do this,” he tells me, “or you’re going to burn out fast.”

“Why, then, would you want to be a Brit?” I ask him.

“Because, as I said, their story from then is a lot like ours right now …”

We both grin: “Broke!”

Freedom Trail Guide
Photo/Art by Matt Kalinowski
For her Freedom Trail début, author Pippin Ross dons 18th-century dress to portray Rachel Walker Revere, second wife of patriot silversmith Paul Revere.

About a minute after sitting down with Sam Jones, it’s obvious that my raw enthusiasm is irrelevant. Seated at a small desk piled with papers, Jones’s disheveled, dark hair and interrogator’s eye contact make it obvious that–having been one of the players since these costumed tours began in 1995–he knows a good performance can’t improve bad content. “I’ve hired a bunch of different people for a bunch of different reasons. That’s why the most important part is your audition,” he says. “I admit I’m a tough audience.”

“Let’s go!” I announce, but don’t add: … before I lose my nerve. I stand and Jones gapes: “No one ever takes me up on the suggestion to do your audition at the actual site you’re going to talk about–cool! Where are we headed?”

“Congress and State,” I tell him.

“The Boston Massacre!” he says. “Extra cool!”

Bolstered by Jones’s 21st-century flattery, my ego quickly deflates when we arrive at the base of the Old State House, which will serve as my impromptu stage. A player in colonial costume is already encamped on the tiny traffic circle, his voice straining above the rush-hour din.

“That’s a rival group started by someone I trained,” Jones remarks. While we wait for the competition to pass, a second gaggle arrives, shepherded by a woman in modern dress. We listen to her mechanically scripted spiel as she describes a nearby site: “The building that once sat here was the Custom House, a formal name for the place where all the money collected from the colonists was packaged and shipped back to England. It was about the most hated place in America at the time …”

Jones shrugs: “In Boston you don’t need a formal license to become a tour guide operator. Any Tom, Dick, or Harry can do it.”

“Or James Otis Jr.,” I respond when I spot the man who launched my urge to become a player as he leads a third group toward my tiny stage.

“Sam! You and your rabble!” Otis shouts out to us. “You’re not dominating my turf, are you?” We politely step aside as he bellows–a stagy, revolutionary lilt in his voice: “This is the Old State House, built in 1712-1713. Look up top–you see the lion and the unicorn? Those are British symbols. The wooden originals were torn down on July 18, 1776, and burned in a bonfire. That’s when the Declaration of Independence was first read from the balcony. We’re also standing at the site of the Boston Massacre …”

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Updated Monday, April 18th, 2011
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