Several events occur in downtown Sarasota throughout the year. Below is just a sample list of events happening in Downtown Sarasota, most of them right in the middle of Pineapple Square! You can view our current events or visit ThisWeekInSarasota.com for all 2008 events happening in the Sarasota area.
| Date | Event Location | Distance from PS |
|---|
| January 7 |
Thunder on the Bay Main St. & Lemon Ave. |
Adjacent to PS |
| January 12 |
Downtown After 5 Main St. & Lemon Ave. |
Adjacent to PS |
| January 14 |
Arts Day Main St. & Palm Ave. |
Walking Distance |
| February 2 |
Jay Foley Art Dedication Main St. & Palm Ave. |
Walking Distance |
February 17 — February 18 | Howard Allen Arts Show Main St. & Pineapple Ave. |
Adjacent to PS |
| March 2 |
First America Bank Opening Main St. & Palm Ave. |
Walking Distance |
| March 17 |
St. Patrick's Day Main St. & Lemon Ave. |
Adjacent to PS |
March 24 — March 25 | Howard Allen Arts Show Main St. & Pineapple Ave. |
Adjacent to PS |
| May 5 |
Cinco de Mayo Main St. & Lemon Ave. |
Adjacent to PS |
May 19 — May 20 | Spring Craft Show Main St. & Lemon Ave. |
Adjacent to PS |
| May 28 |
Memorial Day Parade Main St. |
Adjacent to PS |
| June 16 |
White on State State St. & Lemon Ave. |
Walking Distance |
| June 29 |
Boat Parade/Block Party Main St. |
Adjacent to PS |
| July 1 |
Off-Shore Boat Race Sarasota Bay |
Walking Distance |
| July 1 |
Powerboats by the Bay Display Van Wezel |
1 mile |
| July 4 |
Moscow Circus for Kids JD Hamel Park |
Walking Distance |
| July 4 |
Fireworks at the Bayfront Sarasota Bay |
Walking Distance |
August 8 — August 11 | Sarasota Slam — WBS Marina Jack's |
Walking Distance |
| September 2 |
Labor Day Regala Ken Thompson Park |
Walking Distance |
| September 15 |
Light the Night Walk Ken Thompson Park |
Walking Distance |
| October 13 |
Hispanic Latino Fest Main St. & Lemon Ave. |
Adjacent to PS |
October 20 — October 21 | Howard Allen Art Show Main St. |
Adjacent to PS |
| October 27 |
Halloween Extravaganza Main St. & Lemon Ave. |
Adjacent to PS |
| October 31 |
Pineapple Scare Monster Ball Pineapple Square |
Adjacent to PS |
| November 4 |
Sarasota Reading Festival Main St. & Pineapple Ave. |
Adjacent to PS |
November 5 — November 7 | Sarasota International Design Summit Ritz Carlton Hotel Resort & Spa |
Walking Distance |
| December 1 |
Christmas Parade Main St. |
Adjacent to PS |
| December 7 |
Christmas Tree Lighting Ceremony Main St. & Lemon Ave. |
Adjacent to PS |
December 12 — December 31 | Selby Lights in Bloom Selby Gardens |
1 mile |
| December 21 |
Christmas on Palm Palm Ave. |
Walking Distance |
December 23 — December 24 | Shopping with Santa Main St. & Palm Ave. |
Walking Distance |
| December 31 |
New Year's Eve Celebration Main St. & Lemon Ave. |
Adjacent to PS |