I Love stock Island

Experience the I Love Stock Island Festival 2025 – Florida Keys Weekend of Music, Art & Local Flavor

I Love Stock Island Festival 2025: A Celebration of Island Culture

The I Love Stock Island Festival 2025 returns with a packed weekend schedule from Friday, June 13 to Sunday, June 15, offering a full slate of events that showcase Stock Island’s cultural charm, culinary creativity, and community-driven spirit. Designed for locals and visitors alike, this annual celebration invites everyone to experience the island through history tours, live music, food events, family fun, and artistic discovery.

Up The Keys History Tours kicks off the weekend on Friday, with one-hour air-conditioned van tours exploring the island’s storied past. Tours depart at 10 a.m., 11 a.m., and 1 p.m. and offer a fascinating glimpse into the unique history and characters of Stock Island. In the evening, head to Cayo Hueso Brewing for a classic Low-Country Shrimp Boil from 5:30 to 9 p.m., where freshly cooked shrimp, sausage, potatoes, and corn meet local brews for a savory start to the festival.

Saturday’s events begin with a Collaborative Land-and-Sea Clean-Up from 8 to 11 a.m., led by First State Bank, Monroe County Sheriff’s Office, Key West City Ploggers, and Oceans Edge Watersports. Volunteers help beautify local canals and coastlines, reinforcing the island's dedication to community and sustainability. At Beards & Brews Barbershop, a Father-Son Haircut Special offers a free haircut for junior with Dad’s service—plus a celebratory toast at the in-shop bar. Call ahead to reserve. The day culminates at Bernstein Park with a Festival for the Family from 4 to 8 p.m., featuring live music, a local artisan market, food and drink vendors, kids’ activities, and a silent auction benefiting the SOS Foundation. Admission is free with a canned-good donation encouraged.

On Sunday, festival-goers can catch an encore of Up The Keys History Tours before closing out the weekend at The Perry Marina and Bad Boy Taqueria & Tequila for a Father’s Day Pool Party from 2 to 6 p.m. This lively event offers live music, craft cocktails, raffles, and sun-soaked relaxation, with proceeds supporting the SOS Food Pantry.

Festival-long attractions include a Self-Guided Mural Art Tour, encouraging visitors to explore the island's colorful walls with an interactive map, and a Festival Hashtag Hunt—snap and share moments using #ilovestockisland for a chance to win shout-outs and prizes.

For a weekend immersed in Florida Keys culture, Stock Island offers an experience that’s rich in flavor, fun, and local pride.

Learn more at ilovestockisland.org.