There is always something going on in Sumter County!

Use this event calendar to plan your vacation, or check out what’s going on around you during your stay. Whether you want to attend a local festival or relax while listening to live music, it’s easy to see what’s going on.

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America 250 Community Roadmap

September 2026

Indulge in the Film

September 20 • 1:30 PM - 5:00 PM • Wildwood Vineyard and Events • 1945 E CR 462 • Wildwood, FL 34785

Indulge in the Film is a wonderful 7 course meal and movie experience done monthly at Wildwood Vineyard for more info and to reserve your seat click on this link:...

Wildwood Vineyard logo with gold hexagon and purple grapes.
Sunday
20
September

October 2026

Indulge in the Film

October 11 • 1:30 PM - 5:00 PM • Wildwood Vineyard and Events • 1945 E CR 462 • Wildwood, FL 34785

Indulge in the Film is a wonderful 7 course meal and movie experience done monthly at Wildwood Vineyard for more info and to reserve your seat click on this link:...

Wildwood Vineyard logo with gold hexagon and purple grapes.
Sunday
11
October

Indulge in the Film

October 18 • 1:30 PM - 5:00 PM • Wildwood Vineyard and Events • 1945 E CR 462 • Wildwood, FL 34785

Indulge in the Film is a wonderful 7 course meal and movie experience done monthly at Wildwood Vineyard for more info and to reserve your seat click on this link:...

Wildwood Vineyard logo with gold hexagon and purple grapes.
Sunday
18
October

Halloween Bash at The Vineyard

October 23 • 3:30 PM - 8:00 PM • Wildwood Vineyard and Events • 1945 E CR 462 • Wildwood, FL 34785

Vendors, Music, Food, Wine, Beer and Fun! Live performances from Thrill the Villages and Music by DJ Jefferey.

Wildwood Vineyard Logo, gold hexagon with purple grapes.
Friday
23
October

Halloween Bash at The Vineyard

October 24 • 3:30 PM - 8:00 PM • Wildwood Vineyard and Events • 1945 E CR 462 • Wildwood, FL 34785

Vendors, Music, Food, Wine, Beer and Fun! Live performances from Thrill the Villages and Music by DJ Jefferey.

Wildwood Vineyard Logo, gold hexagon with purple grapes.
Saturday
24
October
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This corner of Florida is packed with events for families, couples, and individuals looking to explore the community.