Sarasota Oktoberfest – Oct 3–5
German food, beer, polka bands, and fun at JD Hamel Park.
Siesta Key Crystal Classic (Fall Edition) – Late October
International sand sculptors return for incredible sand art displays.
Fruitville Grove Pumpkin Festival – Every weekend
Pumpkin picking, hayrides, fall treats, petting zoo, and more.
Selby Gardens Spooktacular – Oct 26–27
Halloween-themed garden fun for families with costumes, crafts, and live music.
Sarasota Medieval Fair – Weekends beginning late Oct
Knights, jousting, vendors, and immersive medieval fun.
Haunted Sarasota Trolley Tour
A ghost tour on wheels with stories of haunted history.
Sarasota Farmers Market Fall Festival
Pumpkin carving, music, and fall specials from local vendors.
Howl-O-Ween Pet Parade – Oct 19
Dog costume contest and pet parade at Arlington Park.
Downtown Sarasota Art Walk – First Friday
Explore the arts district with wine, music, and open studios.
Sunset Yoga at The Bay – Weekly
Free yoga during the golden hour with waterfront views.
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