There’s nothing quite like going back to your hometown—revisiting old stomping grounds, walking familiar streets, and reminiscing about the good ol’ days.

Enter Baltimore Homecoming, a brand-new initiative taking place October 3-5 that invites accomplished Baltimore expats back to reconnect with their roots and reinvest in the city through a series of private events. Launched in November by cofounders and Baltimore natives Nate Loewentheil, and J.M. Schapiro, this nonprofit project aims to employ the talent and resources of former Baltimoreans who have gone on to make an impact in their fields, such as SoulCycle CEO Melanie Whelan and actor Josh Charles.

With help from leaders in the city’s education, business, arts, and religious communities—co-chairs include actress Julie Bowen and Congressman Elijah Cummings—the one-time locals will participate in neighborhood tours, art and music presentations, talks with area business owners such as Under Armour CEO Kevin Plank, and field trips to local spaces including the Center for Urban Families and Living Classrooms’ Target Investment Zone in East Baltimore.

Loewentheil was inspired by Detroit’s annual Homecoming event, which has garnered more than $212 million in total investments over the past four years. “People from here have a strong sense of connection to the city,” he says. “There’s a reservoir of goodwill for Baltimore around the country that, right now, is untapped.”

The goal is that sharing the stories of local change makers, and connecting them to the honored guests, will help spread positive narratives about the city and encourage giving back. To that end, the nonprofit will be launching the inaugural Homecoming Hero awards to recognize five outstanding community members. Among the nominees is Brittany Young, the founder of social venture B360.

Young says her program’s message, which de-stigmatizes dirt bike riding by teaching local kids the STEM-related skills needed to build and maintain their wheels, goes hand in hand with that of this event. “Both projects are committed to telling positive stories about our city and collaborating with one another to build a stronger and better Baltimore,” says Young, “for now and for the future.”

With more than 400 Baltimore “alumni” invited to this first-ever event, the organizers hope that it will grow in size and scope every year by creating a network of guests devoted to giving back to the city. “I hope that for every year the city holds this event,” says Young, “that more positive examples of who Baltimore citizens are and what we bring to the table spread to the rest of the country.”

Josh Charles is living proof that you can take the boy out of Baltimore, but you can’t take Baltimore out of the boy. A working actor since he was 15, Charles left his hometown to work when he was 16, but remains a Mt. Washington boy at heart, religiously following the O’s and the Ravens and sometimes satiating his craving for crabs with transcontinental deliveries from Obrycki’s.

“I love Johnny Unitas and I hate the Redskins, you know? Things you just can’t help if you’re from Baltimore,” he says, speaking by phone from the New York City set of his new, hit CBS drama The Good Wife. “Anyone who knows me, knows that being from Baltimore is a big part of who I am.”

Charles, 38, grew up surrounded by Baltimore luminaries (father Allan Charles is the chairman and creative director of advertising and public relations firm Trahan Burden & Charles; mother Laura was the longtime gossip columnist for The Sun; and Boogie Weinglass, the basis for Mickey Rourke’s character in Diner, is an old family friend) and got his performing start here, albeit in an unlikely form.

“I used to go to open mic nights when I was [9-years-old],” he says. “I did comedy at the Charm City Comedy Club, which was in Harborplace.”

Even more surprising is his comedic inspiration.

“I snuck some Richard Pryor records somewhere, and I used to listen to them a lot—all the dirty jokes” he chuckles. “I thought he was kind of brilliant, a hero of mine. I used to try to imitate him.”

If the thought of a 9-year-old Charles mimicking Richard Pryor is too much cognitive dissonance to bear—Charles is, after all, probably best known for portraying shy Knox Overstreet in Dead Poets Society—he says the move made perfect sense to him at the time.

“When I look back on it, I definitely was precocious enough that you might want to smack me at times,” he cracks, “but it got me feeling comfortable performing at a young age, on a stage, in front of an audience.”

Proud papa Allan says he had total faith in his son. “He was amazing and the crowds loved him,” he recalls. “He could handle himself in just about any adult situation.”

Charles’s big break came in John Waters’s Hairspray, in which he played Iggy, a regular dancer on The Corny Collins Show.

Filming his first movie in his hometown was an “ideal situation,” he acknowledges. “It was really special to shoot my first movie in Baltimore and with John.”

From there it was on to Delaware to shoot Dead Poets Society and then to New York and L.A. for various roles in TV and film including the critically-praised Aaron Sorkin-created dramedy Sports Night, which ran for two seasons on ABC.

Now, Charles has returned to network television in another well-regarded program. The Good Wife‘s ripped-from-the-headlines premise follows Julianna Margulies as Alicia Florrick, a political wife getting on with her life after her husband was caught in a sex-scandal. Charles plays an old friend of Alicia’s who offers her a position at his law firm. The New York Times says the show, “imaginatively explores how one scorned spouse struggles to get past a life-shattering scandal.” (Charles’s take on the whole wronged-wife-standing-by-her-man phenomenon is succinct: “I just can’t believe so many of them do,” he says.)

Beyond the provocative premise, Charles says he was attracted to the project for all the usual actorly reasons: great cast, good script, and an interesting character to play. “I had never played a lawyer before so I thought it would be kind of interesting to research that,” he says.

Plus, as an added benefit, the New York location lets him visit Baltimore more often.

“Living in L.A., it’s harder to get to Baltimore a lot,” he says. “Now, I come back a lot throughout the year. I come back for a lot of Ravens games. I just jump right on the Acela [train] and two-and-a-half-hours later I’m at my parents house.”

Though visits keep him connected to his roots, Charles hopes to eventually return to Baltimore to work.

“I haven’t filmed anything in Baltimore since [Hairspray] and am not happy about that fact. Can you talk to somebody about that for me?” he quips.

He knows exactly what kind of film he’d like it to be, too.

“Diner is one of my all-time favorite movies,” he says. “It’s the kind of movie I would die to be in because it’s just so Baltimore. It’s a universal story, but at it’s heart, it’s so specific to Baltimore.”

Because of Weinglass’s connection to the movie, a 10-year-old Charles got to visit the set during filming and remembers meeting the cast, particularly Kevin Bacon, who spent time talking shop with the then-aspiring actor.

“It really left an impression on me,” he says, adding that not only would he have liked to act in the movie, he also wishes he had lived the movie.

“I’m sort of removed from that generation, but certainly, I still have that in my bones,” he acknowledges. “Had I been born at a different time, I like to think I would’ve been one of those guys in Diner.”