Celebrate the Weekend with Music, Fun & Tradition in Sarasota, Manatee & Charlotte Counties!

Celebrate the Weekend with Music, Fun & Tradition in Sarasota, Manatee & Charlotte Counties!

Looking for the perfect way to spend your weekend? Whether you love live music, family fun, or celebrating local traditions, these events across Sarasota, Manatee, and Charlotte counties are sure to make your weekend memorable.

Jazz Cabaret: Featuring The American Sirens

Date & Time: August 29, 2025 | 7 PM – 10 PM
Location: Downtown Wellen Park, 19745 Wellen Park Blvd, Venice, FL

Enjoy an enchanting evening of smooth jazz as The American Sirens bring their captivating performance to Wellen Park. This event is perfect for a night out with friends or a romantic evening under the stars.

Freedom Festival

Date & Time: August 30, 2025 | 6 PM – 9:30 PM
Location: CoolToday Park, 18800 W. Villages Pkwy., North Port, FL

Celebrate freedom and community with live entertainment, food vendors, and a dazzling firework display to light up the night sky. Bring the whole family for an evening of fun and tradition.

77th Annual Labor Day Regatta

Date & Time: August 30–31, 2025
Location: City Island, 1717 Ken Thompson Pkwy, Sarasota, FL

Experience the excitement of the annual Labor Day Regatta, a beloved tradition bringing together sailors and spectators from across the region. Enjoy scenic waterfront views, competitive sailing, and a festive atmosphere by the bay.

Plan Your Weekend!

Which event will you be heading to? Whether you're drawn to the rhythm of jazz, the excitement of fireworks, or the timeless tradition of sailing, there's something for everyone this weekend.