Beachside’s Biggest Bug Contest & Songwriter Rounds

Join us at Beachside Resort & Residences for a summer night of incredible live music and community vibes. We’re kicking things off with our 2nd Annual “Biggest Bug” Contest—a friendly Mini Season showdown to find the biggest catch of Day One. Then, stick around for the main event: sunset songwriter rounds poolside, featuring a stacked lineup of Nashville artists sharing their songs and stories. Free, family-friendly, and open to the community—come for the lobster, stay for the music. How to enter:

• Arrive to Beachside Resort with your catch between 5:30pm and 6:30pm.

• Live lobster must be weighed in by the fest team on Thursday, July 29th at the weigh-in booth, Poolside at Beachside Resort.

• Enjoy drinks from Chicken Walk and stay tuned for results.

• Winners will be announced on stage at 6:30pm to kick off the Sunset Poolside Rounds. 

Prizes include:

1st Place: $1000 cash prize

2nd Place: $300 gift card to Tavern N Town

3rd Place: $150 gift card to Tavern N Town

Songwriters Lineup:

• Alyssa Flaherty

• Shawn Camp

• Aniston Pate

• Brooke Lee

• Rob Snyder

• Channing Wilson

• Dave Kennedy

• Aaron Raitiere

• Jade Sanders

Jul 30, 2025

4:00 - 9:00 PM

FROM POOLSIDE TO BEACHSIDE

YOUR KEY WEST RETREAT AWAITS

Beachside resort
3841 N Roosevelt Blvd

Key West, FL 33040

FROM POOLSIDE TO BEACHSIDE

YOUR KEY WEST RETREAT AWAITS

Beachside resort
3841 N Roosevelt Blvd

Key West, FL 33040

FROM POOLSIDE TO BEACHSIDE

YOUR KEY WEST RETREAT AWAITS

Beachside resort
3841 N Roosevelt Blvd

Key West, FL 33040