A group of musicians singing together on the dimly lit stage of the Ryman Auditorium during a John Prine tribute. In the center, a woman in a bright orange suit stands with crutches, flanked by other performers including a woman in a red dress and several men in casual stage attire. They are all smiling and singing toward a microphone against a dark, textured backdrop. — Fiona Prine (center) during a You Got Gold concert at The Ryman in Nashville, Tennessee in October 2022. Credit: Madison horn / Hello In There Foundation

John Prine was a sundae kind of guy, and his ice cream order was shameless.

“He liked scoops of strawberry and the chocolate sauce, and then the whipped cream, and the cherry on top,” Fiona Prine told Creative Loafing Tampa Bay. “He was like a little kid.”

Fiona, for her part, loves caramel, and the “99,” a European soft serve cone speciality topped with a chocolate Cadbury Flake. Her husband, who died six years ago after contracting COVID-19, was also partial to 99s. “It’s a very special treat,” she said.

Let It Be, she added, was the shop they would visit while staying at their Gulfport home, which they bought in 2005. This weekend, Fiona brings her own special treat to a community that’s embraced the Prines.

“How Lucky Can One Man Get,” is a concert documentary that captures a 2010 benefit show inside the auditorium of John’s Maywood, Illinois high school. It showcases the singing mailman’s signature charm and storytelling, but has only screened a handful of times. His songs, which lovingly embrace every side of humanity in a way no other American songwriter ever could, are on full display during the 90-minute special.

Three local screenings, happening Friday-Sunday at the Beach Theatre just four miles from Gulfport, are all sold-out. But Prine fans have more chances to connect with each other thanks to tribute concerts happening across Pinellas.

Gulfport’s North End Taphouse & Kitchen—a four-minute walk from the Prine home—hosts a no-cover show and fundraiser on Saturday starting at noon. On Sunday from 2 p.m.-5 p.m. at Safety Harbor’s Crooked Thumb Brewery, more of the greatest songwriters in the Bay area will play songs from the Prine catalog as part of the annual Crooked Piece of Time tribute show.

“It’s one of the very few times that I actually get to just show up, where I don’t have to do any work ahead of time,” Fiona added. “Gail and the community down there are just amazing. I love them all so dearly.”

Gulfport remembers John Prine

Time Sat., April 11, 12-4 p.m. 2026

Location The North End Taphouse & Kitchen, 2908 Beach Blvd. S, Gulfport

Last year, Fiona talked to CL about her husband’s kindness and more.

Last moth, Fiona told CL that she absolutely remembers John writing songs at the Gulfport house after spending time driving and processing his observations about the headlines and life in general. She was also forced to move Prine’s famous yellow legal pads, with Black sharpies and lyrics, out of the Gulfport home after Hurricane Helene ravaged the neighborhood in 2024.

“I haven’t counted the individual notebooks, legal pads, but I probably have at least three boxes full to the top,” she said. “Office boxes that are full, and not every page is filled, but there’s lines written.”

The events are driven by Gail Gilchrist, a longtime Prine family friend, and Celine Thackston, Executive Director of the Prince family’s nonprofit Hello In There Foundation.

Six years after her husband’s death, Fiona acknowledged that as time moves on, people do, too. For better and worse, she’s thrown herself into the distraction of work. But her family—including three sons, Jody, Jack and Tommy, plus others—is well. They’ve even welcomed a fourth and fifth grandchild over the last four months.

“There’s nothing else happening in the world when you look into the eyes of a little child,” she said, noting how important it is to protect them as the country becomes a version of itself that is not necessarily reflected in John’s deeply empathetic catalog.

A vintage, slightly sepia-toned candid photo of John Prine and Fiona Whelan Prine in a convertible. John, wearing sunglasses and a black t-shirt, leans over from outside the car to look at a book or pamphlet held by Fiona. Fiona sits in the passenger seat wearing sunglasses and a sleeveless top, smiling as they look at the pages together. — John (L) and Fiona Prine Credit: Jim Shea / Hello In There Foundation

Gulfport, she added, has always been a refuge for the Prine family. But despite all the time they spent in the state, Fiona said that she and her husband didn’t consider themselves Floridian.

“I think we would have considered ourselves Gulfportian,” she said. “I still do regard that community as just a beautiful haven of love in the midst of things that go on in that state that scare the hell out of me. I just think Gulfport is a very unique community, and I think that’s no surprise that John and I would have been drawn to it.”

So it’s no surprise that proceeds from the screenings and concerts will benefit the Hello In There. The Prine family’s nonprofit has helped countless locals and organizations with both public and private donations.

To date, the foundation has given away $1.4 million to more than a hundred organizations across the country. It’s currently in the due diligence phase of figuring out where it’ll direct funds for 2026.

And Fiona still hasn’t sold the Gulfport home either. Her whole Irish family has even visited and made memories there. It’s a connection that will be there forever, whether she moves back in or not.

I joked that she should open a shop that serves those 99 ice creams from back home.

“Now that you said that out loud, you know the voice I’m going to hear telling me that for the rest of my life,” she laughed.

Her husband, she explained, would’ve said, “Geez, he was right. Fi, that’s not a bad idea. You’d be really good at that.”

John, Fiona said, always reminded her to take care of herself. He also thought she was good at everything. And she bought into that. “I believe him deep down, I do, because he saw me,” she said.

John saw all of us. This weekend, a town that embraced him gets to sing his songs and see each other, too. How lucky, indeed.