October 1–31, 2026
Destin Fishing Rodeo
Destin Harbor • Daily weigh-ins 10:00 AM–7:00 PM
This month-long coastal tradition is an easy outing from Caribe, with free public weigh-ins behind AJ’s Seafood & Oyster Bar. Residents can watch anglers bring in impressive catches, enjoy the harbor atmosphere, and combine the visit with lunch, shopping, or a sunset walk around Destin Harbor.
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October 15–25, 2026
The 39 Steps
Emerald Coast Theatre Company at Grand Boulevard
This fast-paced comic spy thriller offers Caribe residents a convenient evening of live theater close to home in Miramar Beach. It is a good adults’ night out or date-night option, especially for locals who want entertainment without driving far toward Fort Walton Beach or Panama City.
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October 24–25, 2026
Mattie Kelly Arts Foundation Festival of the Arts
Mattie Kelly Dugas Pavilion Green, Destin • Saturday 9:00 AM–5:00 PM; Sunday 10:00 AM–4:00 PM
Residents near Caribe can spend a fall weekend browsing work from more than 100 artists, watching demonstrations, hearing live entertainment, and enjoying food and children’s activities. Admission and parking are free, making this a particularly accessible family outing within a short drive of Miramar Beach.
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October 24–25, 2026
2nd Annual Destin Songwriter Festival
Destin Harbor
This waterfront music weekend is a strong regional choice for Caribe residents who enjoy live music and local stories. Multiple stages feature established songwriters and rising artists, with free side-stage performances alongside ticketed programming, so visitors can build an evening around the harbor without committing to a full concert package.
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October 31, 2026
Boo at Baytowne: Trick or Treat Street
The Village of Baytowne Wharf, Miramar Beach • 6:00 PM–8:00 PM; fireworks at 8:00 PM
Baytowne Wharf’s free Halloween celebration is one of the most convenient family activities for Caribe residents. Children can trick-or-treat through the Village streets, while parents enjoy the festive setting and shops; the evening ends with fireworks, creating a memorable local Halloween outing without a long drive.
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October 31, 2026
Halloween on the Boo-ulevard
Grand Boulevard, Miramar Beach • 4:00 PM–6:00 PM
Grand Boulevard’s merchant trick-or-treating event gives local families an easy, walkable Halloween activity close to Caribe. Kids can come in costume, collect candy, and enjoy the seasonal atmosphere while adults browse restaurants and stores, making it a practical early-evening option before other Halloween plans.
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