“I walked up on the stage, and I was like, ‘Oh my goodness. All these people are here to see us right now.’”

During Cakeswagg’s first freestyle gigs aboard the Roxbury school bus, she never pictured herself pursuing rap music as a career. So, being billed at the Boston Calling Music Festival over Memorial Day weekend was a “bucket list” experience for the up-and-coming hip-hop artist.

Cakeswagg was one of the many performers to hit the festival’s Orange Stage, which exclusively featured New England-based acts.

“Especially when you live here, [Boston Calling] is just one of the things that feel like maybe it could be attainable, but you don’t want to get your hopes up too high,” she said. “And then it just happened.”

Cakeswagg described how “the most beautiful thing about [her] artistry” is her connection to her peers, friends and family who saw her potential before she saw it herself.

“It was big for all of us,” she said. “They believed in me and helped me to believe in myself.”

Her Saturday set embraced collaboration, as she performed alongside her DJ and Boston-based choreographer of five years, who helped organize numbers for her many backup dancers.

“You want dance to be a part of ensembles and things bigger than yourself,” she said. “As performing artists, this is what we want to do.”

For other Bostonians hoping to kick-start their music careers, Boston Calling is an opportunity to break out as an artist beyond the confines of the Charles River.

Fresh off his graduation from the Berklee School of Music and just days before moving out of Boston, singer Kieran Rhodes closed out this collegiate chapter of his life with his Boston Calling set Friday.

Rhodes cites musical influences like Billy Joel, James Taylor and Randy Newman, all of whom helped shape him into the artist he is today.

“There’s not really anybody that’s doing the ‘Piano Man’ thing right now,” he said. “I’m gonna fill that space.”

Rhodes said he hopes to honor the type of music that precedes his generation, crafting a musicianship that “doesn’t exist anymore in music today.” Each show, he said, is simply about stepping out on stage with a band and playing music, without any gimmick.

“I’m very, very grateful for the experiences that I’ve been able to have over the past four years,” he said. “This stuff doesn’t happen for everybody, and I realize that.”

For Madi Diaz, returning to Boston gave her a “really nostalgic feeling” as a former Berklee student herself. Despite performing solo, accompanied only by her guitar on the giant Green Stage, she embraced the opportunity to engage the festival crowd. 

“There was a lot of room up there,” she said, laughing to herself. “I feel like we just try to do our best no matter the size of the stage.”

Big stages, however, are not unfamiliar to Diaz. In 2022, she accompanied Harry Styles’ “Love On Tour” arena circuit only to be asked to join his backing band the next year. In April, she opened for Kacey Musgraves on the “Deeper Well” tour.

“It’s kind of always fun to come back [to Boston],” she said. “The crowd was really wonderful today.”

Cakeswagg said playing a festival like Boston Calling, especially so early in her career, is something any performer aspires to.

“All the work that we do,” she said. “This is like a dream.”