Fall & Winter Event Extravaganza: Festivals, Art, Music, and More Across Southwest Florida

Southwest Florida plans dozens of events from October through April, with festivals, art shows, plays, and holiday fun spreading across Naples, Marco Island, and Fort Myers. 

At the Bailey-Matthews National Shell Museum, Shelloween brings spooky fun on Oct. 18 and 25. Kids can hunt for treasures, peek into decorated tanks, and make gooey slime. Those who dress as sea creatures get free entry during the Oct. 25 costume contest. 

The German American Social Club hosts Cape Coral's 40th Oktoberfest on Oct. 17-19 and Oct. 24-26. Buy tickets now for $8 or pay $10 at entry. Traditional food, music, and crafts fill the grounds. 

Kids can trick-or-treat with costumed characters at the Naples Zoo's Boo at the Zoo from Oct. 17-19. The fun runs from 9 a.m. to 1 p.m. and is included with standard admission. 

On stage this fall, the Naples Players present two shows. Agatha Christie's And Then There Were None runs through Oct. 19. Ada and the Engine starts Oct. 15 and continues until Nov. 9. Each show costs $55. 

Starting Nov. 6, the Marco Island Center for the Arts opens its new season with Sam Bobrick's Baggage, running through Nov. 23. Watch all five shows this season for $175 (members) or $200 (non-members). 

Marco Island starts the winter season with its First Old World Christmas Bazaar at Veteran's Park, Nov. 29-30. Shop from local makers while sipping drinks and hearing carols. 

Music fans can catch Darius Rucker at Live Fest on Dec. 13, with tickets from $150 to $355 for VIP access. 

The Marco Island Christmas contest returns Dec. 15-17 for its 32nd year. Judges will tour the island's streets on December 19, picking winners across nine areas.