Ever wondered what it takes to become a costumed Freedom Trail guide in Boston? To start, you’ve got to be good with dates.

I’m on Boston’s Freedom Trail walking tour only out of loyalty to a history-buff pal, not my personal interest. I whisper to my friend, “History … boring …” when a man dressed in a tricornered hat and knickers announces, “Let’s go see how America was born.” He says his name is James Otis Jr., the pro-bono legal firebrand from the 1700s who stated, “Taxation without representation is tyranny!”

“Hey, how come I didn’t know about you?” I ask tourmaster Otis.

“Because I ended up insane, in a very hush-hush sort of way,” he replies, channeling the disgraced colonial lawyer.

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As we meander on, the dish gets dirtier. Turns out, after the midnight ride, Paul Revere remained a no-big-deal local silversmith until 86 years later, when poet Henry Wadsworth Longfellow urged, “Listen, my children, and you shall hear / Of the midnight ride of Paul Revere …” John Hancock was probably a bootlegger. Benjamin Franklin left Massachusetts in disgrace. Samuel Adams–the tax collector, not the ale–was seriously delinquent on his own debts after driving the malt business he inherited from his father into the ground …

—

My office window peers down onto Tremont Street, epicenter of the Freedom Trail. After the tour, my attitude is different. I smile when I pass by my old friend James Otis Jr., a little disturbed by how he coolly ignores me to stay in character while telling his story to an enraptured circle of strangers. When I see a tour happening, I slow to catch a bit of the performance. “Eavestrailing” is so easy that I cross the street and quicken my step to catch up with the tour. My
history-buff friend asks, “What are you, a Freedom Trail stalker?”

In full skirt-and-bonnet costume, an actress playing Paul Revere’s first wife, Sarah Orne Revere, is heading back to Boston Common after wrapping up a tour at Faneuil Hall. I swoop in beside her. “What’s it like?” I ask.

She turns to me with a polite, maternal gaze. “What’s it like wearing a costume from the 1700s in the middle of 21st-century downtown Boston? Being Paul Revere’s wife? Or being a Freedom Trail player?”

“A player?” I ask.

“That’s what we’re called, instead of ‘guides,'” she explains, with a slight trace of tour fatigue. “We take on characters who lived here around the time of the Revolutionary War. Sarah died before the war, but had a strong influence on Paul’s revolutionary spirit.”

“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!”

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

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 …”

In my own competitive stirring, I watch the crowd for signs of boredom, listening for choice one-liners to pilfer. “Lobsterback! Go back to England!” Otis quotes an epithet yelled out by a member of an angry pack of colonists. Hmm … I think I can use that one someday. Otis continues setting the stage: “The Boston Massacre began when locals started flinging snowballs laced with oyster shells at the Brits …” As if reading my line-stealing mind, Jones whispers, “Don’t feel as though you’ve got to get every single fact in.”

Finally, it’s my turn before a professionally critical audience of one. I take a last peek at my script and heave a hopeful breath: “It was March 5th, 1770. There was tension … everywhere,” I try in a darkly dramatic voice. “Out in front of our Custom House where our customs–a fancy word for money–were being bagged and shipped, a soldier with a musket was posted ’24/7,’ as we say these days. A nice young lad named Edward Garrick, an upstart barber’s apprentice, did what we all wanted to do as he walked past the soldier. ‘You’re a bloody-backed scoundrel!’ he barked at the soldier. That’s an 18th-century version of ‘Get lost, ya skank!'”

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?”

“Boredom.”

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.

I put on my “stay,” a rib-suppressing corset, followed by a “shift,” the relaxed name for an uncomfortable vest-like dress top. Lacing up, I peer down at my girdle-nudged breasts.

“Don’t worry,” Rudy offers. “You’ll hide all of that with the chemise you’ll wear underneath.” He gestures toward a dense collection of what appear to be nightgowns. “In founding our country, warmth, health, and safety trumped British high-period correctness and French decolletage,” he explains.

As I adjust what appear to be bags of mobile cellulite around my waist (intended to give my hips a whole lotta breadth), it’s clear that despite dropping a few petticoats over the years, women have always been expected to keep the ripe-‘n’-fertile look alive–then, now, and probably forever.

“Can I do three or four tours a day in summer and feel comfortable that these clothes are all mine?” I wonder aloud.

“Don’t worry–your undergarments get washed a couple times a week, 21st-century-style,” Rudy reassures me.

Jones enters the room. “So, who’d you pick?”

“Paul Revere’s second wife, Rachel,” I reply.

“That’s like auditioning for college theater as Hamlet!” Rudy exclaims. “Soooo overdone!”

“What he means is that someone is already playing Paul Revere’s first wife, Sarah,” Jones explains.

“I know,” I tell him. “That’s part of why I picked Rachel.” While tending to the crops and an ultimate total of 11 children (including the six surviving kids of her deceased predecessor, Sarah), Rachel Walker Revere stood by her man even after it was pretty obvious he’d plagiarized engraver Henry Pelham’s drawings of the Massacre, and in them made the martyred black man, Crispus Attucks, a white man. Rachel claimed it was her fault–that she’d borrowed all of the brown paint. To defend my choice, I talk theater: “The battle of the wives could make for some good dramatic tension.”

Jones sighs: “Remember, this isn’t reality, it’s history …” He pauses. “Oh wait,” he says, “history is reality.”

Back on Chauncy Street, I exhale, convinced that once costumed and on the Trail, I’ll be a great player. A pack of yakking urban office workers, hightailing it back to their cubicles with lunch bags and cigarettes, take me away from my fantasy by letting me know I need to get out of their way.

“Pray, pardon me,” I say, offering the colonial version of “Excuse me” as I step aside. “Good morrow!” I throw in. A couple of them turn to me with the cheerful expression that only something surprisingly pleasant brings. In that moment, I know: I am a player.

For more information on Freedom Trail tours, visit: thefreedomtrail.org

Pippin Ross

Becoming a Freedom Trail Player