Songwriters Fest Hits Key West with Free Show by Brad Paisley

Songwriters Fest Hits Key West with Free Show by Brad Paisley - A group of people standing in front of a crowd - Key West
Singer-songwriter legend Robert Earl Keen returns to the festival. CONTRIBUTED

The Key West Songwriters Festival is more than just an island party with a great oundtrack. The festival, in its 24th year, is the largest of its kind in the world.

Organizer Nadene Grossman, who has been with the festival for 20 years, thinks back to the early days. “I remember when all the songwriters would fit on one poster. I would pick them all up at the airport,” said Grossman.

The event has certainly grown over the years. This year, the festival is welcoming over 200 performers. An exciting element for music lovers is that any one of those 200 performers could be the next Chris Stapleton (one of the small names on Grossman’s 2005 poster) and there’s no underestimating the bragging rights of seeing someone like that on a pool deck in Key West. The same excitement holds true for the organizers. Grossman says, “I love that I’ve been involved for this long and can look back and see top-tier performers when they were up-and-coming artists. You never know who’s going to be the next number-one hit songwriter.”

Legends and up-and-comers take to various stages around the island to play music and share the stories behind famous recordings. With so many talents converging on a small island, what’s the best way to tackle this itinerary of fun? Not to worry, we’re here to help uncover hidden gems, cheap outings, and parties worth the price.

Local Best Bet

Sometimes it’s worth a short Uber ride to bust out of the Duval scene and find some open space to kick back. In recent years, the Sunset Green, located at the 24 North Hotel on North Roosevelt Boulevard, has become a local-friendly location for live music in Key West. This year, they are serving up tons of programming for the Songwriters Festival. The main sets take place on Saturday, May 11. Beginning at 1 p.m., visitors can throw down a blanket, grab a cocktail and camp out for three hours of songs and stories.

1 p.m. – Emily Landis, Alyssa Miceala, Ava Suppelsa
2 p.m. – Bridgette Tatum, Meg Linville, Lauren Morrow
3 p.m. – Cliff Cody, Lance Carpenter, Adam Wood

Additionally, the Green offers daily music events during the festival including karaoke, live DJ performances and a special outdoor screening of “Bohemian Rhapsody” on Friday, May 10 at 8 p.m.

Daily freebie highlights

With season tapering to an end, many locals are feeling the financial squeeze that comes with rising temperatures. Fortunately for Key West, the Songwriters Festival offers a slew of free programming.

Friday, May 10 is field trip day. Take a trek to Stock Island to catch the 3 p.m. performances at the pool of the Perry Hotel. Locals know – this is one of the best waterfront spots in the Keys. The Green Parrot hosts a 5:30 p.m. sound check and 10 p.m. show, allowing plenty of time to find your way home.

It’s no secret that the biggest, boldest freebie of the week takes place on Saturday, May 11. At 8:40 p.m., country legend Brad Paisley takes the stage for a block party concert on Duval Street, in front of Sloppy Joe’s.

Worth the splurge

Tired of fighting the crowds and feeling a ‘spendy’? Treat yourself. For $125, music lovers can enjoy rock star status at the Closing Sunset Show at Truman Waterfront Amphitheater. Tickets include premium view table seating, a buffet dinner featuring Caribbean cuisine and an open bar. For those who prefer to save and pregame at one of Key West’s famous happy hours, tickets to the show only are available for $25 ($40 at door). Either option is a stellar deal to access the all-star line up of James Slater, Channing Wilson, Dave Fenley, Ronnie Bowman, Paul Cauthen, Lee Roy Parnell and Randy Houser. Seating begins at 6 p.m.

The bottom line on Songwrtiters Festival is that there are no wrong choices. With over 200 performers, taking the stage at venues all around Key West, for five straight days, there is something for everyone.

“I love the way the festival has evolved over the years,” said Grossman, “and how this little community has embraced it.”

Local Spotlight: Nick Norman

It’s one thing to be a local music lover, soaking up the blissed-out atmosphere that blows into town for a week. What’s it like to be a local musician during the liveliest live music week of the year? We caught up with one of Key West’s favorite songwriters, Nick Norman, to get his perspective on the festival.

“The Songwriters Festival has been an excellent tool for networking. I believe Key West is a home to some of the greatest songwriters and performers in the world. It can be difficult to find a solid platform to showcase our original material in the bar scene, and the festival has helped to open that door. I believe we, as a town, will continue to become more of a place that promotes creativity in songwriting. The link between the songwriting communities of Nashville and Key West, now Texas as well, is a perfect fit. Key West has a ton of stages to perform our songs and test out new material, which to me is one of the most important parts. Thanks to Charlie Bauer and the Key West Songwriters Festival for their continued work to shine the light on songwriting as a respected form of art in Key West…my home.” Locals can catch Nick Norman after the festival at The Key West Theater Speakeasy Series Sunday, May 19 at 8 p.m.

The Key West Songwriters Festival
Various locations, Key West
Wednesday, May 8 – Sunday, May 12
Most shows are free
To purchase admission for ticketed shows, visit

Join Our Blast – Keys News Right to Your INBOX

Leave a Reply