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Becoming a Freedom Trail Player

I throw in corollaries on past and present domestic battles, such as British taxes and Wall Street scams; democracy and health-care reform. I toss around adaptations of infamous Hollywood one-liners: “‘We’re mad as hell, and we’re not going to take this anymore!'” from the 1976 film Network. I try out jokes by describing the Revolution-triggering Townsend Acts as “broad and pointless as … my skirt” (although I’m wearing form-fitting blue jeans).

Jones’s critique: heavy on performance, light on facts. “On a 1 to 10? I’ll give you a 7,” he concludes, generously. “Come back next week and we’ll try some costumes on. Have you decided on a character?”

Clearly, the preferred characters are the “interesting” underdogs we don’t know about. Besides James Otis Jr. and Sarah Revere, there’s Ebenezer Mackintosh, a shoemaker who led a mob in destroying the homes of Chief Justice Thomas Hutchinson and Stamp Act administrator Andrew Oliver–a wealthy Boston merchant and a symbol of the elite who ruled the colonies while happily kissing England’s micro-managing butt. My list is small. With the exception of Abigail Adams and Martha Washington, Revolutionary War women are far less widely known than their men.

In honor of Betsy Ross, the Philadelphia woman I nearly picked, I’m humming The Star-Spangled Banner as I wander into the small, crowded costume room. “That song was written after the attack on Fort McHenry in Baltimore–the War of 1812,” offers a man dressed as a pirate. My competitive comeback: “Still, it was a war against the Brits!”

He smiles. “Going to be a player?”

I nod. “Maybe,” I say. “What’s the hardest part of this job?”


Josh Rudy plays the privateer Daniel Malcolm–a colonies-sanctioned pirate allowed to raid any British ship he wants. His infamy so perturbed British soldiers that his gravestone’s claim–“a true son of Liberty”–still has deep dents in it from enemy musket balls taking sacrilegious potshots. “Not our boredom,” he quickly adds, “the customers’.”

“Boredom is an easy fix,” notes Kim Carrell, a.k.a. Captain Silas Talbot, a high-seas warrior whom George Washington ultimately put in charge of the USS Constitution after the Revolution. “[The real problem] is the class-act alpha male–the person every performer knows as a heckler,” Carrell explains. “They don’t care if they’re right; they just want to compete.”

“Hecklers are easy,” Rudy counters. “When they quiz you with arcane questions like ‘Who was the wife of the mayor of Lexington?’ I just say, ‘I’m a pirate! Who cares?'”

Turns out only the veterans take on the junior-high-school trips. “Give yourself a solid year before trying to win their attention,” Carrell offers. “Even if they like you, they won’t show it. That hurts in the early player days.”

Arms loaded with a heavy bundle of 18th-century clothing, I sit, eager for more advice from the Trail’s battle-scarred vets. “The best technique is to be a politician out there,” Carrell continues. “When you get a direct question, give back a long, rambling answer. By the end, they either forget they asked a question, or they’re thinking, ‘Hmm, there must have been an answer in there somewhere.'”

“Eccentricity works,” Rudy weighs in. “‘Are you a pirate?’ they ask. ‘No,’ I say back. ‘I steal and kill for the good of America!’ Sometimes I’ll just snarl, ‘Aaahhhhyyyyyeeee matey!'”

I start to dress in my “period clothing”–the word costume isn’t allowed. A thin layer of 21st-century T-shirt and leggings enables co-gender outfitting. I turn to Michael Szkolka, the Brit from the elevator. “Excuse me, but why are your under … pants … pleated?”

“They’re called breeches. That’s so I can comfortably spread my legs when I get on a horse,” he tells me.

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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