Return to Content

Becoming a Freedom Trail Player

Becoming a Freedom Trail Player
1 vote, 5.00 avg. rating (89% score)

“How did you get this job?” I ask.

She reaches down, grabs a handful of hem, hikes it just high enough for a fast exit, and says over her shoulder, “Talk to Sam Jones.”

“Bring a head shot and your resume, and we’ll talk,” says Sam Jones, the creative director of the Freedom Trail Foundation, over the phone. “We’re not looking so much for history professors. What we really like is a good storyteller.” He offers a tour caveat: “There are certain topics you definitely must hit, but the rest is your thing …” He then adds, ominously, “How are you on dates?”

1765 was the Stamp Act … I whisper to myself as I wait for the elevator to the fourth-floor Freedom Trail offices on Chauncy Street in the heart of downtown Boston. England was broke and taxed everything printed, from newspapers to birth certificates, by insisting they carry revenue stamps. 1770 was a snowball fight that went bad and turned into the Boston Massacre. 1773, the Boston Tea Party … 1775, Paul Revere’s ride, Lexington, Concord …

“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!”

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.”

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.


Bring New England Home

Get a Free Trial Issue when you subscribe to Yankee Magazine

In this issue: 

  • 65 Best Summer Events
  • The Elusive Promise of the Maine Tides
  • The Easiest Clambake You'll Ever Make

Subscribe Today

No comments yet.

Leave a Reply

We reserve the right to remove or edit comments that are offensive or disrespectful to our readers and/or writers, cannot be verified, lack clarity, or contain profanity. Your comments may be republished by Yankee Magazine across multiple platforms.

Register Sign In

©2015, Yankee Publishing Inc. All Rights Reserved.
Yankee Publishing Inc., | P.O. Box 520, Dublin, NH 03444 | (603) 563-8111