Fall Events in Sarasota

Summer might be winding down, but Sarasota, Florida, fall events are just getting started. While summer might have been filled with sunny skies and countless days on the beach, the changing season ushers in slightly cooler weather and a slew of things to do.

Read on to learn about some of the best fall events in Sarasota County.

72nd Annual Labor Day Regatta

As summer turns to fall, locals and visitors to Sarasota await the annual regatta, which takes place on Labor Day each year.

This decades-old event is much loved in Sarasota County, drawing well over a thousand visitors each year. Watch dozens of billowing white triangles dot the bay, racing in different categories and age groups.

Free for spectators, the Labor Day Regatta has been a Sarasota staple for almost 75 years and has become one of the best fall events in Sarasota County for the whole family. This year, the Labor Day Regatta takes place from September 1 to 2.

Siesta Key Triathlon

Lace up your shoes for Siesta Key’s annual triathlon, both a test of endurance and a lot of fun.

Swim, cycle, and run the race of a lifetime along some of America’s best beaches. First launched in 1985, this annual race begins with a 0.3-mile swim in the Gulf of Mexico, along the shores of Siesta Beach.

Then, cycle a 13-mile path that loops back to Siesta Beach. Here, you’ll run along the sugar white sands of this famous beach for a three-mile, out-and-back run.

The race takes place on September 22 at 7 a.m., starting near the lifeguard towers on Siesta Beach. All proceeds go toward the Sarasota YMCA Sharks Swim Team.

Girls Inc. Totally Tailgate 2018

Save the date for the 3rd Annual Totally Tailgate benefiting Girls Inc. of Sarasota County!

This year’s co-chairs – Heidi Anderson, Stephanie Beauchamp Kempton, Mary Pat Radford, and Shana Fitzpatrick Zamikoff invite you to join them for the largest tailgate party under


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one roof with fan favorite food and drinks, classic games, live music by Version 3.0, raffles, multiple screens to watch your favorite football games and the opportunity to brag about the team nearest and dearest to your heart!

Come out and represent your favorite team and support Girls Inc.! Sponsorships are available and a perfect way to highlight your business. Individual tickets are $100. Game day attire encouraged. For more information call Morgan Gerhart, 941-366-6646 x 207.

Fish for United Way

Fishing is a huge part of Florida culture, gastronomy, and economy – what better way to experience it than a fishing tournament for a good cause?

The annual Fish for United Way fishing tournament is an opportunity for visitors and locals alike to cast their best line, all vying for the top prize: $1,000. Anglers will reel in bass, crappies, and catfish in Lake Parrish, the Florida Power and Light Plant’s reservoir.

The cost to enter is $250 per boat, and proceeds go toward three local United Way locations across the region. Start practicing your angling for this benefit tournament on October 6.

Sarasota Chalk Festival

The Sarasota Chalk Festival is a much-awaited annual event for street art aficionados. The festival brings together a truly impressive group of artists that create colorful, detailed drawings using everybody’s favorite childhood artistic tool: chalk.

This year’s theme is “Garden of Wonder,” celebrating where the natural world and human imagination meet. Hundreds of artists will try their hand at depicting flowers, leaves, vines, and branches using the pavement as their canvas over this four-day event.

The festival will feature both traditional and 3D pavement art, as well as other events and activities at the Venice Airport Fairgrounds from November 10 to 13.

Ringling Underground

Rock out at The Ringling Museum of Art this fall on the first Thursday of every month. This recurring event brings local music to the “stage” in The Ringling’s courtyard.

Sway and bob to the beats of contemporary live music under a purple spotlight against a backdrop of Florida palms. Artists offer an eclectic mix of tunes from in and out of state. Works from up-and-coming artists will be on display in the courtyard for the event.

The fall dates for The Ringling Underground are set for September 6, October 4, and November 1.


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For any information on Sarasota neighborhoods, events, where to stay, and where to invest in real estate, give me a call today at 941.266.0529.

I can help you find the perfect vacation rental, second home, or investment property, so you can enjoy the best fall events in Sarasota in luxury and comfort.


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