Somewhere along the way, my travels picked up an unexpected little side quest – visiting the places connected to America’s famous icons before they even became famous. Being a history fanatic that I am, these visits have been one of the most inspiring moments of my life. Each experience was different. The houses these people came home to, the hometown they were born in, the neighborhoods they walked through, the schools they attended, all told a different story but with one thing in common – the beauty of humble beginnings. This, perhaps, was what made them so interesting
We usually meet famous people at the other end of their stories. We know Michael Jackson filling stadiums around the world. We know Michelle Obama walking through the White House. We know Barack Obama standing behind the presidential podium, Viola Davis accepting an Oscar and Matthew Perry sitting in that famous Friends apartment.
But every one of those stories started somewhere much less glamorous.
5. Williamstown, MA
Home to Williams College, one of the highly regarded liberal arts college often grouped among the “Little Ivies,” Williamstown is a small, picturesque New England town in the Berkshires, a completely different setting from the Los Angeles world most people associate with Perry and the frenetic Chandler Bing character that made him famous.
While Perry was born in Williamstown, he spent most of his formative years in Canada, which makes his connection to the town easy to miss. There is something lovely about discovering these unexpected connections while traveling. You can visit somewhere for its scenery, history, food or architecture but learning that a person known around the world took their very first breaths there makes it pretty special if you ask me. Friends will forever be one of my favorite sitcoms so visiting Williamstown was special.
4. Central Falls, RI
Central Falls made me think about just how far a life can travel.
Viola Davis was born in South Carolina, but her family moved to Central Falls when she was only two months old, and this small Rhode Island city became the place where she grew up. In her memoir, Finding Me, She has spoken openly about a childhood marked by poverty and hardship, but also about discovering acting and beginning to imagine a life beyond the circumstances around her.
So while I was in Central Falls, I made a point of visiting Central Falls High School, where Davis graduated in 1983. Standing outside the school felt a little different from visiting a birthplace or childhood home. A high school is such an ordinary part of growing up. It is where you spend years trying to figure out who you are, what you are good at and, if you are lucky, what you might someday become.
For Davis, those teenage years came at a time when acting was beginning to feel like a real possibility. At 15, her talent earned her a scholarship to a summer performing arts program, and she later studied theater at Rhode Island College before continuing on to Juilliard. Knowing what came afterward makes standing in front of that high school pretty remarkable. The girl who grew up in Central Falls would eventually become an EGOT winning actress, but at one point she was simply a student walking through those halls with a dream that had barely begun to take shape.
3. Gary, IN
Gary was the stop on this list where the contrast between the beginning and what came after felt the most dramatic. The fact that I visited this place after watching the Netflix movie Michael made the trip more emotional and memorable.
Michael Jackson was born in Gary in 1958 and grew up with his family at 2300 Jackson Street, in a small two-bedroom house that Joe and Katherine Jackson bought in 1950. The Jackson children lived tightly packed into the home, and it was there that Michael and his brothers rehearsed before the Jackson 5 became famous. It sits on an otherwise ordinary residential street, and if you somehow did not know its history, you could easily drive past without realizing that one of the most famous entertainers in the world once lived there.
This was before Motown, before the Jackson 5 became international stars, before Thriller, the moonwalk, sold-out stadiums and the kind of fame that would eventually make Michael Jackson recognizable almost anywhere in the world. Before all that, there was Gary, and there was this little house. The family’s musical story was already beginning to take shape here. Just a few blocks away, Michael is believed to have given one of his earliest performances at his elementary school, and the Jackson brothers later won a local talent show before their career took off. The family eventually left Gary for California in 1969.
Gary has held onto Michael Jackson’s legacy in a very personal way. After his death in 2009, fans traveled from around the country and beyond to gather outside the house, leaving flowers, notes and tributes. For the city, he has remained one of its most recognizable connections to the rest of the world.
What stayed with me most, though, was the scale of it all. There is something almost unbelievable about standing in front of such a modest home and thinking about how far the life that began there eventually traveled.
If ever there were a reminder that extraordinary stories can have very ordinary beginnings, this house would be it.
2. Oahu, HI
Of all the people on this list, Barack Obama gave me the most places to actually follow. Instead of visiting just one childhood home or school, I found myself tracing several chapters of his early life through Honolulu: the hospital where he was born, the school he attended, the apartment building where he lived with his grandparents, and even where he had his first job. Obama was born in Honolulu on August 4, 1961, at what was then Kapiʻolani Maternity & Gynecological Hospital, now part of Kapiʻolani Medical Center for Women & Children.
From there, I made my way to Punahou School, the private college-prep school Obama attended from fifth grade until his graduation in 1979. Founded in 1841, Punahou is one of Hawaii’s oldest and best-known schools, and even before knowing its connection to Obama, the campus immediately feels like a place with history behind it. There is something a little surreal about standing outside a school and thinking about the fact that a future president once walked those halls as a student. Before the speeches, campaigns and presidency, he was simply a teenager in Honolulu, going to class, playing basketball and figuring out who he was. Schools have a way of reminding you that great people start out in the most ordinary way.
I also stopped by Punahou Circle Apartments on Beretania Street, the high-rise where he lived with his grandparents, Stanley and Madelyn Dunham, during much of his childhood in Honolulu. Obama himself later described growing up with them in a small two-bedroom apartment, and his grandmother continued living in the building for decades.
My tour did not end here, I then proceeded to Obama’s first ever work place. Long before politics, Obama’s first summer job was scooping ice cream at a Baskin-Robbins in Honolulu. He later joked that scooping row after row of hard ice cream was tougher on his wrists than he expected, but said the job taught him responsibility, hard work and how to balance work with the rest of his life.
I love little details like this because they make famous people feel considerably less distant. A future president once had a first job just like millions of teenagers do, standing behind a counter and serving customers. That was what made following Obama’s Honolulu story so enjoyable for me. I was not visiting grand presidential monuments. I was visiting a hospital, a school, an apartment building and an ice cream shop. All incredibly normal places. And yet together, they tell the story of a boy growing up in Hawaii long before the rest of the world knew his name.
Obama’s life would eventually take him far beyond Hawaii, through college on the mainland, Chicago, the U.S. Senate and ultimately the White House. But part of that journey began here, in Honolulu, with his grandparents, his school and the everyday experiences of growing up on Oahu.
1. Chicago, IL
Save the best for last, they say! Visiting Michelle Obama’s childhood home was especially special because Chicago is my favorite city. I have spent years listening to her podcast, reading her books, and hearing her talk about growing up on the South Side, so by the time I made my way to Euclid Avenue, the house already felt strangely familiar to me.
One image in particular had always stayed in my mind: the Robinson family gathered around the kitchen table. Through Michelle’s stories, I had imagined that table so many times, the conversations, the laughter, the lessons from her parents, and the everyday family moments that helped shape who she would become. So standing outside the actual house where so many of those stories took place felt a little surreal. This was no museum or grand historic landmark. It was an ordinary family home on an ordinary Chicago street, and somehow that made it even more meaningful.
I found myself looking at the house and thinking about Michelle not as the First Lady, bestselling author, or public figure we know today, but simply as Michelle LaVaughn Robinson, a girl growing up with her parents and brother on the South Side. After reading so much about those years and hearing her tell those stories in her own voice, being there felt almost like stepping into a chapter of a book I had already read many times.
The Robinson family did not occupy the entire house. Michelle, her parents and her brother Craig lived in the apartment upstairs, while her great-aunt lived downstairs. Somehow, knowing that made the house feel even more intimate to me. This was a family sharing a modest two-flat, building their lives within a relatively small space, and creating the kind of home Michelle would later describe so vividly in her books and conversations.And maybe that is why this stop felt different from the others. I wasn’t simply learning that someone famous had once lived there. I already knew the stories. I had imagined the rooms, the family, and especially that kitchen table. Now, for the first time, I was standing right outside the place where those stories began.
Visiting these homes, schools, streets and neighborhoods reminded me that every extraordinary life begins somewhere ordinary. Before the awards, the presidency, the sold-out arenas and the worldwide recognition, there were family homes, classrooms, first jobs, grandparents, siblings and communities quietly shaping the people they would become (it trully does take a village). That is what I loved most about making these stops. They were not grand monuments to fame; they were glimpses of the beginning. And now, whenever I travel somewhere new, I find myself wondering whose story may have started on an unassuming street, in a small house, or inside a school I might otherwise pass without a second thought. And maybe that is the real joy of travelling.
This little detour isn’t over yet. I already have Kosciusko, Mississippi on my list, where Oprah Winfrey took her first steps long before the talk show and the empire. Rosario, Argentina keeps calling too, the streets where a young Messi first kicked a ball around before the world knew his name. I’m excited for what lies ahead.
Happy wandering!