All Jake, all the time in wildly successful ‘Flamingo’ weekend

People all around Vero Beach were likely to have crossed paths with country music star Jake Owen at some point during “The Flamingo 2025,” his recent three-day charity weekend. Funds raised benefit the Jake Owen Foundation, which supports various local organizations and the St. Jude Children’s Research Hospital in Memphis.

Like a real-life version of “Where’s Waldo?,” Owen was seen on the golf course, the football field, the stage, an airport runway and hangar, and even along the shoreline, turning his annual Flamingo weekend into a community-wide, star-sighting scavenger hunt.

“I started the Jake Owen Foundation in 2015 to give back to the community that gave so much to me growing up,” said Owen, a Vero native who moved to Nashville two decades ago to chase his country music dreams.

“With my success as a country singer, I realized I could use my platform to raise money for charitable causes. Each year, thanks to the unwavering support of Vero Beach, we’ve grown, added more events, and raised more money. That’s what philanthropy is all about.”

The whirlwind began Friday with the Flamingo Golf Classic at the Quail Valley Golf Club, where Owen hit the greens alongside the likes of golf legend John Daly. By evening, he had traded the fairway for nostalgia, returning to his alma mater, Vero Beach High School, to help kick off their winning home football game. Minutes later, he had raced across town to Riverside Theatre to introduce the Flamingo Comedy Jam featuring Sheena Reagan and Jamie Lissow.

Bright and early Saturday morning he was joined by a huge group of eager fans and runners for the Flamingo Family Fun 3K at the Vero Beach Airport. From there, it was straight over to Heaton’s Reef, where the poolside crowd soaked in the breezy acoustic performances by Maddox Batson, Josh Del, Anna Vaus and Matt Pingel, artists personally selected by Owen as rising singer-songwriters to watch.

Saturday night Owen delivered the weekend’s Flamingo Jam showstopper. Under the soaring roof of the Corporate Air hangar, he rocked out on the stage, backed by powerful guest performances from Lexi and Trey Pendley and Grammy-winning country heavyweight Kendell Marvel.

The intimate setting and fantastic music kept the energetic crowd on its feet and cemented the night as the highlight of the Flamingo festivities.

Sunday wrapped up the marathon weekend with Owen’s annual fishing tournament, a tradition that reels in the fun and closes out the fundraising.

“The foundation has raised nearly $10 million for over 65 causes, helping people right where they live and love,” said Owen.

“This is about serving others and making a difference. If this weekend showed anything, it’s that one person, and one community, can change lives. I hope it inspires the next generation to give back and build something that helps people too.”

Known for his laid-back style and such signature hits as “Barefoot Blue Jean Night” and “Beachin’,” Owen’s music has long captured the coastal, carefree spirit that shaped him, earning gold and platinum records, 10 No. 1 singles, and an ACM Award.

He is now stepping into a new creative chapter, with “Dreams to Dream,” his eighth studio album and first release as an independent artist after more than a decade with RCA.

Produced by Shoot Jennings, it returns to Owen’s soulful, old-school roots, blending country standards with original tracks to create a reflective, emotionally honest look at life, aging and renewal.

“Have you ever woken up from a great dream and wanted to go back to sleep to see what happens next?” he asked.

“That’s where I’m at. I’ve had an incredible career, and now I want to see what comes next.

‘Dreams to Dream’ is about accepting where I am in life and looking forward to the next chapter. The songs are raw and honest. I just want to do me.”

Owen is also exploring new ventures, including the purchase of a building in his hometown of Kingston Springs, Tenn., where he plans to open a restaurant. Another dream in the making.

And just like that, the weekend ended the way it began, with Owen seemingly everywhere at once, lifting spirits, raising money, and reminding Vero Beach that even when his career takes him around the world, he always finds his way back home.