🏡💚 Corcoran Connect Realty Presents: May 2026 Events in Clermont – Sunshine, Soul, and Local Style!

May in Clermont is a beautiful blend of waterfront relaxation and high-energy celebration. Whether you are seeking a day of healing, a night of 80s rock, or the tropical vibes of a reggae festival, the "Choice of Champions" has it all this month. At Corcoran Connect Realty, we believe your community should be as inspiring as your home. As Your Real Estate Concierge, we’ve gathered the most exciting events happening in Clermont this May! 🏡💚

Community Favorites & Weekly Traditions

1. Family Food Fest (First Saturday Food Trucks)  

• Date: Saturday, May 2, 2026  

• Time: 4:00 PM – 8:00 PM  

• Location: Historic Downtown Clermont
• Cost: FREE AdmissionGather your family for a local favorite! 🚚🌮 Stroll through the historic streets while enjoying a rotating lineup of the region’s best food trucks, live music, and family-friendly activities.  

2. Southern Hill Farms: Spring U-Pick & Fun Zone  

• Date: Select dates through May (Saturdays/Sundays recommended)
• Time: 9:00 AM – 4:00 PM  

• Location: Southern Hill Farms, 16651 Schofield Road  

• Cost: Ticket/Entry Fee requiredCelebrate the harvest! 🍓🚜 Pick fresh berries and enjoy the kid-friendly Fun Zone. It’s a perfect Saturday outing for those looking to experience Clermont’s agricultural charm.  

3. Downtown Clermont Farmers Market  

• Date: Sundays: May 3, 10, 17, 24, 31, 2026
• Time: 9:00 AM – 2:00 PM  

• Location: 752 West Montrose Street  

• Cost: FREE AdmissionBrowse over 60 vendors offering fresh produce, handcrafted goods, and artisanal soaps. 🥕🌻 It’s a beloved Sunday morning tradition in the heart of our city.

Music, Healing & Island Vibes

4. The Hat Bar Experience

• Date: Saturday, May 9, 2026
• Time: 10:00 AM – 11:30 AM
• Location: Waterfront Park, 2nd St.  

• Cost: $20.23 (Registration required)Get creative by the water! 👒 Design your own custom hat at this trendy, hands-on workshop right at Waterfront Park.

5. May Wine Stroll

• Date: Friday, May 15, 2026  

• Time: 6:30 PM – 9:00 PM
• Location: Historic Downtown Clermont
• Cost: Ticket Purchase RequiredExplore downtown boutiques while sampling a variety of unique wines. 🍷 Check-in at 756 West Montrose Street to receive your glass and wristband for the night!  

6. Women's Day of Healing

• Date: Saturday, May 16, 2026
• Time: 11:30 AM – 5:30 PM
• Location: Silhouette Island Sanctuary
• Cost: Registration RequiredA truly unforgettable experience designed especially for Breast Cancer Thrivers. 🌸 This day of wellness and connection provides a supportive sanctuary for healing and peace.

7. Sunglasses at Night Rocks the Cove!

• Date: Saturday, May 16, 2026
• Time: 2:00 PM  

• Location: Cypress Cove Marina and Resort, 10354 Cypress Cove Lane
• Cost: FREE AdmissionThe 2026 season kicks off with a bang! 🎸🕶️ Enjoy electrifying 80s anthems by the waterfront. It’s the perfect high-energy atmosphere to make unforgettable summer memories.

8. 2026 Clermont Reggae Festival

• Date: Saturday, May 23, 2026  

• Time: 2:00 PM – 9:00 PM  

• Location: The RasState, 9117 Jack Underwood Road  

• Cost: Ticket Purchase RequiredTransport yourself to the islands! 🏝️🥁 Enjoy live performances by the iHeritage Band and other top reggae artists. It’s a day of soulful rhythms, island vibes, and great community energy.

Arts, Learning & Connection

9. Medicare Made Easy with Ryan Schalk

• Date: Wednesday, May 13, 2026
• Time: 1:00 PM
• Location: Cooper Memorial Library
• Cost: FREEA helpful and informative session for our local seniors looking to navigate their benefits with ease. 🩺

10. Clermont Matters: Community Update

• Date: Wednesday, May 27, 2026  

• Time: 9:00 AM – 10:00 AM
• Location: Clermont Historic Village
• Cost: FREEStay in the loop! 🏘️ Join local leaders to learn exactly what is happening downtown directly from the people making it happen.  

11. Laughter For Social Change – Comedy Show  

• Date: Wednesday, May 27, 2026  

• Time: 6:00 PM
• Location: The Station
• Cost: Ticket Purchase RequiredEnjoy a night of comedy with a purpose! 🎭 This event raises awareness for ACES (Adverse Childhood Experiences) through the power of laughter.  

Whether you’re exploring the shops downtown or dancing at a waterfront reggae festival, Clermont is a city that champions a vibrant lifestyle. At Corcoran Connect Realty, we are honored to be your local experts. If you are ready to buy or sell in the Clermont area, let Your Real Estate Concierge handle every detail so you can get back to enjoying the fun! 🔑💚

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