Introducing history-lovers to Detroit’s chronicled characters, tour-guide Bailey Sisoy Isgro is an equivalently exuberant character

American playwright Arthur Miller once said, “There are no such things as stories, only characters.” In other words, people are important. They are faceted and complicated creatures full of fears, flaws, quirks and contradictions. That’s what makes them wonderful and it’s certainly what has always made things interesting — particularly in Detroit.   

“Very few human beings besides my grandma are perfect,” Bailey Sisoy Isgro, founder of Detroit History Tours, says. “But that doesn’t diminish their significance or contribution.”

Bailey was born and raised in Detroit, just like her parents and her parents’ parents and their parents’ parents. The fifth-generation Detroiter grew up on coney dogs, Vernor’s floats and family anecdotes. These stories were her first introduction to the city’s infamous inhabitants.

“My grandpa was a great storyteller. He would take his time and had a way of making whomever he was talking to feel important,” Bailey says of the man who used to wear an I knew Henry Ford button and who loved sharing his account of an afternoon Ford rode by on his tractor and stopped to dig out a swimming hole for a bunch of poor kids.

“In Detroit, you walk in the shadow of all these ghosts,” Bailey says. “You can’t be here, either as a visitor or a resident and not wonder who was here before you.”

Bailey’s mother was quick to recognize and nurture her daughter’s curiosity. It was common for the family to take leisurely walks through the neighborhood cemetery, and if Bailey expressed interest in a particular gravestone, her mother would escort her to the library to read about the life of the dearly departed.

Fast forward a couple of decades, to a sunny Saturday afternoon in Detroit and Bailey is back in a cemetery — Woodlawn Cemetery. This time, with a microphone in hand and a bus full of 50 new friends hanging on her every word.

The Terrifying History Tour, one of several historical tours Bailey has charted, is a five-hour journey through Detroit’s dark side — each stop exploring the factories, pubs, parks and institutions where former citizens straddled the line between good and evil. Naturally, drinking and swearing are as much a part of the tour as they were a part of Detroit’s colorful past.

“This all started out as a hobby,” Bailey says. “A way to give back to Detroit, for everything it’s given me. I honestly thought we’d do four tours a year, and eventually, if things went well, once a month — max. Last year, only our second in business, we did 200.”

Bailey can and does rattle off dates and numbers with extraordinary ease, but she’s learned it’s the stories about real people that actually help others connect to the city and care about its future.

“I want people to walk away from our tour with a little more context,” Bailey says. “If you are reading the paper and see Fisher Body Plant 21 is being torn down, I don’t want you to see Fisher 21. I want you to see Howard Fisher, the youngest of the seven Fisher brothers, who was made to go sweep up the scrap metal on the factory floors every evening to be recycled. Because even though he was an executive, he was still the little brother. And though they were millionaires, the Fishers never forgot their humble beginnings and couldn’t stand to see a penny wasted.”

Detroit is special. There was, and is, always something happening here and Bailey has made it her life’s mission to share that fact, in the most interesting way possible, with whoever is interested. And according to the numbers, a lot of people are interested. Some 6,500 people a year come from near and far — as far away as Australia — to listen to Bailey and her ebullient team wax poetic on everything from Detroit’s wild women to its Purple Gang.

Patrons walk away understanding how Detroit changed the way the world makes everything, how it helped save the world during WWII and why you have the Motor City to thank for things like stop lights and peanut butter. If after the tour, you find yourself a little more in love with Detroit, and have a newfound kinship with its residents, past and present, that’s intentional, too.

“The Cadillacs, the Fords, the Dodge brothers, the Fisher boys, the Riveting Rosies — they may not be here physically, but these people are so tangible to me that I have crushes on some of them,” Bailey says. “I think Edsel Ford is just dreamy. John and Horace Dodge were a riot by all accounts and would have made for a memorable double date. I think Marie Therese Cadillac and I would have been friends, and I know I would have had some great heart-to-hearts with Sojourner Truth. Then there’s Harry Bennett, an evil goon who I can’t help but love because he made Walter Reuther fight harder for auto workers’ rights. Can you have Batman without the Joker?”

Despite the success of Detroit History Tours, Bailey hasn’t quit her day job.

“I work full time as an automotive sculptor for GM,” she says. “While it’s a lot to juggle, I can’t quit because I’m one of those annoying people who loves both of her jobs. I get to work at the GM Technical Center in Warren, which is a National Historic Landmark. I get to walk the same halls that Harley Earl, Alfred Solan and The Damsels of Design walked. And when I get home, I get to scheme new ways to share Detroit’s rich, riveting past.”

Bailey not only hosts tours, but a wide range of historically themed events around the city. Like a scavenger hunt at the Detroit Institute of Arts, a Depression-era luncheon and discussion at Hamtramck’s iconic Bank Suey community space, and a historical fashion show in the living room of her Highland Park home, once owned by the infamous Motor City Madam, Helen McGowan. This December, she and her creative cohorts will recreate the Repeal Ball of 1933 at The Detroit Yacht Club in the very same ballroom Detroiters celebrated the end of American prohibition 85 years ago.


Somehow, in between sculpting the future and preserving the past, Bailey found the time to add another dream job to her resume: Author. In collaboration with her friend and fellow tour guide Nicole Lapointe, Bailey wrote a picture book titled Rosie: A Detroit Herstory. The book celebrates Rosie the Riveter and the women war workers of WWII. You wouldn’t be surprised to learn that Bailey wrote it in the very same bar that working women frequented after their shifts. Wayne State Press will publish the book this spring and the ladies have plans to release a new Herstory every year.

“Every morning, I wake up thinking I am the luckiest girl in Detroit,” Bailey says. “Where else can a 30 year old own a company like mine, while having a job like mine, while getting to live in a house like mine, with neighbors like these? And also be on a first name basis with every bar owner in town?”

Maybe Detroit’s the lucky one. It’s the wildly charming, extraordinarily clever and slightly rebellious characters like Bailey Sisoy Isgro who have always made living within these 142.9 square miles an adventure.