Cassadee Pope and Friends Deliver Intimate Island Performances at Keys to Country Concert Series

West Palm Beach, Florida native Cassadee Pope returned to the Sunshine State for the 8th installment of the Keys to Country music series at Hawks Cay Resort, April 8-9 in the Florida Keys. Pope was joined by fellow country singer-songwriters Trent Tomlinson, Emily Shackleton, Ronnie Bowman, Keith Gattis, Jeff Garrison, and Sarah Darling for the two-day event.

The exclusive concert series is limited to guests who book the Keys to Country package at Hawks Cay Resort, which includes two nights or more plus admission for two guests per hotel reservation or four guests per villa reservation. In 2021, the country music series kicked off by selling out in less than two weeks. Previous headliners have included Lee Brice, Michael Ray, Joe Nichols, Easton Corbin, Tyler Farr, and the Warren Brothers. 

Hawks Cay Resort, the home of Keys to Country, is a luxurious destination for a relaxing getaway or an action-packed family vacation. The secluded island features seaside dining, interactive dolphin encounters, tranquil pools, aquatic adventures, spa experiences, and much more.

After a day of lounging by the pool or diving into the resort’s activities, Keys to Country brought the intimate vibe of a Nashville-style songwriter round to resort guests at the waters’ edge of the aptly named Oasis Cay. What makes this type of show unique is how the songwriters share the stories behind the songs, banter with each other on stage, and interact with the crowd. Perched on stools and armed only with an acoustic guitar or keyboard, the stripped-down setting pulls the audience into the creative process with the songwriters.   

Friday night’s show began with singer-songwriter Sarah Darling performing a song called “Coastin,” which was the perfect complement to the warm breeze that filled the air and the swaying palm trees. She was joined by Jeff Garrison, who performed songs that he’d written with RaeLynn and Lori McKenna, among others.

Ronnie Bowman and Keith Gattis closed out the first night’s performances with iconic country songs they wrote, some of which were recorded by superstars Brooks & Dunn and Kenny Chesney. Bowman opened with “It’s Getting Better All the Time,” which reached the top of the charts in 2005. Gattis delivered a poignant version of “El Cerrito Place,” originally recorded by Charlie Robison, then recorded by Kenny Chesney, who made it a top 10 song on the Billboard Country Airplay chart.

The second and final night of Keys to Country started with singer/songwriter Emily Shackleton, who performed “Doin’ Fine,” which was recorded by Lauren Alaina. She also performed songs recorded by Carly Pearce (“What He Didn’t Do”) and Runaway June (“I Know the Way”). Shackleton was joined on stage by Trent Tomlinson, who had success early in his career with the heart-wrenching “One Wing in the Fire.” In addition to songs he had success with as an artist, Tomlinson also performed hits he’s written for other artists, like Brett Young’s “In Case You Didn’t Know.” 

Before headliner Cassadee Pope, winner of Season 3 of The Voice, took the stage, the resort auctioned off two acoustic guitars that were autographed by all the artists from the weekend to raise money for a local food bank. Hawks Cay Resort raised $7,000 for Keys Area Interdenominational Resources (KAIR), bringing the grand total to $24,000 of funds raised since the inception of the music series. 

Pope chatted with Country Now ahead of her performance about the unique opportunity to take the stage at a stunning resort, her current album Thrive, and her dream lineup for a “y’alternative” festival.

“Getting to be here in Florida at one of my favorite places ever… it’s so awesome,” said Pope. “I went snorkeling yesterday. And it’s nice to end the night with just watching friends play and it kind of brings a little bit of Nashville on the water, which is pretty fun.”

The Keys to Country series puts a spotlight on country songwriters, who are the artisans of country music, which is important to Pope.

“I was really, really lucky coming to town after The Voice, being embraced by the songwriting community in Nashville. It’s the culture, it’s what keeps the wheels spinning. Without the songwriters and without the community, there are no hits, there are no artists making it. So it is really special to kind of be embraced by that. It also just made me a better writer,” said Pope.

“I lacked a direction a lot with my lyrics and I also was challenged just by the amazing melodies people come up with. And I’ve always loved melodies. That’s my, I think my strength in my writing, but being challenged by some of the best melodic gods and goddesses in Nashville was so fun.” 

The “Wasting All These Tears” singer released her current album, Thrive, in October 2021 after a challenging, but fruitful writing and recording experience. 

“It was bizarre,” recalled Pope. “I wrote everything on Zoom… which I’d never done before. And I gotta say it just opened up a part of my brain that felt really free because I was just in a comfortable place. I knew my dogs, I could let them out whenever they needed to go out. I knew they were taken care of. I knew where the snacks were. I knew where the coffee was and I could stay in my PJs and I was just very comfortable.”

But when it came to recording the album, the priority was safety over comfort. “We really just wanted to keep the exposure to each other like super short,” Pope revealed. “So unfortunately, we all had to wear masks and we took tests beforehand and we got in and out of the studio with the full band in two days, which was crazy.”

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Pope just wrapped up her Thrive tour, where she frequently sported a shirt on stage with the word “Y’alternative” on it. When asked if she could create a lineup for her own ‘y’alternative’ festival, her face lit up at the idea. “I would hope to have Paramore, because they’re Nashville, she’s from Franklin, so that would be fitting,” said Pope. “I would ask Devin Dawson. He’s pretty alternative. I would ask Morgan Wade, she’s got some alternative vibes. I’d probably ask Breland. He’s got like country and a little bit of pop. And I don’t know if she would do it, but I would ask Shania Twain, cause she’s got rock and roll in there. And I’m just gonna throw in Michelle Branch because she’s one of my favorites and I feel like she fits as well.”

Pope closed out the Keys to Country weekend with her unique blend of “y’alternative” music during an hour-long set that included her debut single “Wasting All These Tears” and a surprise collaboration with boyfriend Sam Palladio on her first number one song “Think of You,” originally recorded with Chris Young. She also included a fun cover of Whitney Houston’s “I Wanna Dance With Somebody (Who Loves Me)” and a throwback to her former rock band Hey Monday with the song “Candles.”

At the end of the night, resort staff teased the next installment of the Keys to Country concert series, asking attendees to save the date for this August.

For more information about the Keys to Country concert series and Hawks Cay Resort, visit https://www.hawkscay.com/