10 Things to Do in Sarasota This September 2025

September in Sarasota brings a mix of waterfront adventures, outdoor festivals, live music, and family fun. Whether you’re a local or visiting for the weekend, here are ten can’t-miss events happening around Sarasota and nearby communities.

1. 77th Annual Labor Day Regatta

Location: Sarasota Sailing Squadron, 1717 Ken Thompson Parkway
Date: September 1, 2025
The longest-running annual regatta in the Southeast, this iconic sailing event has been a Sarasota tradition since 1946. Watch competitive sailors from across the U.S. and Canada take to the water on five race courses. Spectators can enjoy free viewing, a Friday night welcome party, Saturday dinner, and Sunday awards ceremony.

2. Music on Main at Lakewood Ranch

Location: Main Street, Lakewood Ranch
Date: September 5, 2025 | 6 p.m. – 9 p.m.
This month’s concert features BABYL with classic rock and soul favorites. Stroll Main Street filled with food vendors, beer trucks, and sponsor booths, while the kids enjoy rides and activities. Bring your chairs, but please leave coolers at home.

3. Exotic Cars on the Circle

Location: St. Armands Circle Park, Sarasota
Date: September 6, 2025 | 9 a.m. – 3 p.m.
Ferrari Drivers of Sarasota return with their annual car show featuring exotic supercars. Admire rare vehicles up close at this free event in one of Sarasota’s most popular shopping and dining districts.

4. Barks and Brews Tailgate Paw-ty at UTC

Location: The Green at University Town Center
Date: September 9, 2025 | 7 p.m. – 9 p.m.
Dog lovers unite for this monthly event supporting Nate’s Honor Animal Rescue. Bring your pup (on a leash) and enjoy live music, craft brews, pet-friendly vendors, and adorable adoptable dogs looking for their forever homes.

5. Movie in the Park at Waterside Place

Location: Waterside Park, 7301 Island Cove Terrace, Lakewood Ranch
Date: September 12, 2025 | 7 p.m. – 10 p.m.
Grab a blanket and chairs for a family-friendly outdoor movie night. The first 450 attendees will receive a free sno-cone from Kona Ice, courtesy of Grace Community Church. Concessions, inflatables, and popcorn make this the perfect evening under the stars.

6. St. Armands Craft Festival

Location: St. Armands Circle, Sarasota
Date: September 13–14, 2025 | 10 a.m. – 5 p.m.
Browse creations from more than 175 artisans at this two-day festival featuring fine art in the park and crafts along the circle. Shop ceramics, jewelry, stained glass, and more while enjoying the unique charm of St. Armands Key.

7. Ski-A-Rees Fall Season Opener

Location: Ski-A-Ree Stadium, 1602 Ken Thompson Parkway
Date: September 14, 2025 | 2 p.m.
Cheer on Sarasota’s own Ski-A-Rees as they kick off their fall water-ski show season. This local tradition delivers high-energy tricks, jumps, and stunts on the bay — free for the whole family.

8. International Coastal Cleanup Day

Location: Various Sarasota County Beaches
Date: September 20, 2025 | 8 a.m. – 10 a.m.
Make a difference by joining volunteers to help clean Sarasota’s beautiful shoreline. Registration is required, and spots fill quickly — so sign up early to be part of this worldwide coastal conservation effort.

9. Edelweiss Oktoberfest

Location: Edelweiss, 611 Manatee Ave E, Bradenton
Date: September 26 – October 26, 2025 | Noon – 8 p.m.
Celebrate Bavarian culture with a month-long Oktoberfest full of live music, authentic German food, beer tents, costume contests, and daily giveaways. Admission is free, and the festive atmosphere is perfect for families and groups of friends.

10. Venice Beach Party

Location: 101 The Esplanade South, Venice
Date: September 27, 2025 | 1 p.m. – 6 p.m.
Head to the beach for live music, food trucks, and cold drinks with sand between your toes. Free parking and a trolley from Centennial Park make it easy to get to this fun-filled afternoon event hosted by Venice Main Street.

Plan Your September in Sarasota
From sailing traditions to beachfront parties, Sarasota offers plenty of ways to enjoy the sunshine and community spirit this September. Mark your calendars and make the most of this lively month!