Sarasota & Siesta Key Events by Season

Whether you're planning a quick beach trip or locking in a winter stay, here is how the Gulf Coast’s annual event calendar takes shape. Use this recurring guide to time your visit, then verify final hours and ticket details with event organizers before heading out.

Year-Round Weekly Traditions

• Siesta Key Drum Circle: Sunday evenings an hour before sunset on the sand south of the main Siesta Beach pavilion.

• Siesta Key Farmers Market: Sunday mornings in Siesta Village Plaza for local produce, baked goods, and island crafts.

• Downtown Sarasota Farmers Market: Saturdays year-round along Lemon Avenue and State Street, featuring regional growers and food artisans.

• Nokomis Beach Drum Circle: Sunset gathering just down the coast at Nokomis Beach every Wednesday and Saturday.

Winter Events: December–February

• Lights in Bloom: Selby Gardens illuminates its bayfront banyans and tropical grounds on select evenings throughout December and early January.

• New Year’s Eve Pineapple Drop: Downtown Sarasota’s block party on December 31, featuring food trucks, amusement rides, and a midnight drop at Lemon and Main.

• Winter Fine Art Festivals: Juried craft showcases and sidewalk art fairs rotate through St. Armands Circle and downtown Sarasota across January and February.

• Fresh Fridays: Downtown Sarasota’s evening pedestrian block party series running through the cooler months; venues and dates change monthly.

• Phillippi Farmhouse Market: Wednesday open-air market at Phillippi Estate Park featuring local food and artisan vendors (runs October through April).

Spring: March–May

• Sarasota Jazz Festival: Downtown venues host national jazz talent, club crawls, and mainstage concerts in March.

• Sarasota Film Festival: Independent features, documentary screenings, and filmmaker discussions take over local theaters each April.

• Run for the Turtles: Early April 5K and 1-mile beach run at Siesta Beach benefiting Mote Marine Laboratory’s sea turtle tagging efforts.

• Suncoast Boat Show: Center consoles, cruisers, and marine exhibits fill the waterfront slips at Marina Jack in April.

• Phillippi Farmhouse Market: Continues Wednesdays at Phillippi Estate Park through the end of April.

Summer Events: June–August

• Sarasota Music Festival: Three weeks of classical masterclasses and orchestral showcases at the Sarasota Opera House in June.

• Fourth of July Fireworks: Annual Independence Day shows over Sarasota Bay and directly off Siesta Beach; check the local holiday lineup for launch sites and parking access.

Fall Events: September–November

• Siesta Key Scarecrow Stroll: Village storefronts feature handmade scarecrow displays throughout October.

• Lights at Spooky Point: Family-friendly Halloween light trail through the historic maritime hammock at Spanish Point in Osprey.

• Fruitville Grove Pumpkin Festival: East Sarasota farm festival with hayrides, food vendors, and pumpkin patches running October weekends.

• Phillippi Farmhouse Market: Opens for the fall/winter season at Phillippi Estate Park starting in October.

• Siesta Key Crystal Classic: Master sand sculptors from around the world compete on Siesta Beach during a four-day November weekend.

• Sarasota Medieval Fair: Jousting, artisan markets, and costumed performances spanning November weekends out at Woods of Mallaranny.

• Holiday Parades & Lightings: Kickoff festivities launch in late November and early December, with separate schedules for the Siesta Key Village parade and the Downtown Sarasota Holiday Parade.

Confirmed Siesta Key Events: October 2026

• October 1–31 — Siesta Key Scarecrow Stroll: Stroll through Siesta Village to spot custom scarecrows hosted by participating local businesses.

• October 31 — Siesta Key Safe Treats: Free trick-or-treating for kids along Ocean Boulevard and across Siesta Key Village from 4:00 PM to 6:00 PM.

To double-check real-time dates, admission fees, or weather updates during your stay, consult the community calendars at the Siesta Key Chamber of Commerce and Visit Sarasota County.