Fall into Fun in Sarasota: 14 Events You Can't Miss this September

September in Sarasota is a time for fun! Whether you’re a local or a tourist, there are plenty of exciting events and activities to enjoy this month. From live music to outdoor adventures, there’s something for everyone in the area. So, grab your sunglasses and get ready to fall into some fun in Sarasota! Here are 14 events and things to do in Sarasota this September that you won’t want to miss.

1) Music on Main

September 1st, 6pm-9pm | Lakewood Ranch Main Street

Music on Main is a free concert series and block party that takes place on the first Friday of every month, and it's a must-attend event for music lovers of all ages! Not only does Music on Main feature fantastic live performances, but it also offers a variety of local food vendors, beer trucks, sponsor booths, and games and activities for the kids.

What makes Music on Main even better is that proceeds from the event go towards supporting a different local non-profit organization each month. This month, the event will benefit Manatee Children's Services, a fantastic organization dedicated to helping vulnerable children and families in our community.

And let's not forget about the music! This month, we have the Taylor Opie Band taking the stage. Their soulful, funky sound is guaranteed to get you up and dancing. So, if you're looking for things to do in Sarasota this September, don't miss Music on Main. It's a ton of fun and all for a good cause!

2) 75th Annual Labor Day Regatta

September 1st-3rd, Hours Vary | City Island

Get ready to set sail at the 75th Annual Labor Day Regatta, hosted by the Sarasota Sailing Squadron! This prestigious event is the longest-running annual regatta in the southeast, drawing hundreds of competitive sailors from across the U.S. and Canada. Open to all classes of sailing vessels, this regatta attracts sailors ages 8 to 80, with a special focus on junior sailors aged 8-18. With a Friday night welcome party, five separate race courses, a Saturday dinner, and a Sunday awards ceremony, the Labor Day Regatta offers a thrilling weekend of sailing and festivities. It's definitely one of the top things to do in Sarasota this September!

3) Breakfast with the Sharks

September 2nd, 8am-9:30am | Mote Aquarium

Are you ready to start your day off with some underwater excitement? Check out Breakfast with the Sharks, a unique experience at Mote Marine Laboratory! Enjoy a light continental breakfast while learning about our favorite finned friends and watch a narrated feeding of the bonnethead sharks. This program is perfect for all ages, so bring the whole family!

Admission fees are $36 for member adults, $40 for non-member adults, $27 for member youth, and $30 for non-member youth. Children 2 and younger get in for free! Please note that Breakfast with the Sharks does not include general admission to Mote Marine Laboratory. Dive into this thrilling experience and make memories that will last a lifetime!

4) Sarasota Bradenton Fall Home Show

September 8th-10th, Hours Vary | Robarts Arena

Visit the Sarasota Bradenton Fall Home Show to improve your home this fall. This event is perfect for homeowners like yourself, no matter what stage of remodeling, landscaping, or decorating you're in. At the Home Show, you'll find a wide range of exhibits showcasing home improvement and remodeling products, with interactive demonstrations and sample interior and exterior vignettes to inspire your creativity. Take advantage of the exhibitors' special show-only discounts and get all your shopping done under one roof.

The event is open on Friday and Saturday from 10 a.m. to 7 p.m., and on Sunday from 10 a.m. to 5 p.m. Admission is $10 at the door, but you can also find free passes online. With free parking and the chance to register online for free admission, the Sarasota Bradenton Fall Home Show is a must-visit for anyone looking to spruce up their home this fall!

5) Exotic Cars On The Circle Car Show

September 9th, 9am-3pm | St Armands Circle

If you're a car enthusiast or simply appreciate the beauty of luxury vehicles, then you won't want to miss the free Exotic Cars On The Circle Car Show sponsored by Ferrari Drivers SRQ. This annual event showcases some of the most stunning and rare cars you'll ever see. From sleek sports cars to elegant classics, the Circle is transformed into a showcase of automotive excellence.

Plus, all proceeds benefit Flight to the North Pole, a charity that provides financial and emotional support to terminally ill children and their families in Sarasota/Manatee Counties. So, grab your camera and prepare to be wowed by the impressive lineup of cars at this year's Exotic Cars On The Circle Car Show!

6) Party on the Plaza

September 9th, 5pm | CoolToday Park

Party on the Plaza is back, featuring Pure Country! Get ready for a night of toe-tapping fun at CoolToday Park. Pure Country of Southwest Florida is a premier country band that knows how to entertain. They'll be performing all the hits from the 80s, 90s, and early 2000s, delivering powerful vocal harmonies that will transport you back to the good ol' days.

Gates open at 5:00 PM, and the music starts at 7:00 PM. Tickets are just $15, but if you're looking to elevate your experience, VIP tickets are available for $120. With VIP tickets, you'll get four tickets with chairs, four beverages (soda, beer, or wine), and a reserved space near the stage. Don't miss out on this incredible evening of country music!

7) 9/11 Commemorations and Remembrances

September 11th, Hours Vary | Various Locations

The University of South Florida Sarasota-Manatee campus will be holding a special remembrance event to honor the victims of the September 11, 2001 terrorist attacks. This event will also pay tribute to the survivors, first responders, members of the military, and their families. Join the commemoration on Monday, September 11, at the Sarasota National Cemetery at 8:30 am.

Additionally, an Anniversary Commemoration of 9-11 will be held at Rossi Park in Bradenton, starting at 9 am. Let's come together as a community to remember and honor those affected by this tragic event.

8) Barks and Brews

September 12th, 7pm-9pm | The Green at UTC

Furry friends and their families are in for a treat at Barks and Brews, a paw-ty that supports Nate's Honor Animal Rescue! This event brings together adoptable dogs, craft brews, live music, and pup-friendly vendors for a tail-waggin' good time on The Green at UTC. Don't forget to bring your friendly dogs (on a leash) and get ready for a night of fun and furry cuddles! Barks and Brews takes place on the second Tuesday of every month from 7 to 9 p.m. It's the perfect opportunity to enjoy a pint while supporting a great cause.

9) International Coastal Cleanup Day

September 16th, 8am-10am | Various Locations

International Coastal Cleanup Day is an important event that brings together communities in Sarasota County to help protect our beautiful coastlines. Held at various locations including Sarasota, Venice, North Port, Osprey, Nokomis, and Englewood, this day is dedicated to cleaning up our beaches and waterways. Did you know that during recent Coastal Cleanups, nearly 500,000 volunteers collected over 18 million pounds of trash? That's an incredible effort! If you want to be a part of this impactful event, be sure to register early and reserve your volunteer spot, as pre-registration is required. Let's work together to keep our coastal ecosystems clean and thriving!

10) Sarasota Opera Food & Wine Festival 2023

September 23rd, 1pm-4pm | The Sarasota Opera House

The Sarasota Opera Food & Wine Festival 2023 is back and better than ever! This year's festival features a lineup of amazing local restaurants, showcasing the best culinary delights the region has to offer. Indulge in delectable dishes and sip on fabulous wines while supporting the Sarasota Youth Opera, one of the nation's top youth music training programs. With live performances and a tantalizing array of specialty foods, wines, and coffees to sample, this event promises a fun, entertaining, and delicious experience.

Don't wait to get your tickets! Purchase them in advance for $75 per person or $85 at the door. Doors open at 1:00pm, with performances by the Sarasota Youth Opera at 2:00pm and 3:00pm. Raffle drawings and ongoing food and wine tastings will keep the excitement going until 4:00pm. Get ready for a mouthwatering afternoon of pure enjoyment!

11) Selby Public Library's 25th Anniversary Celebration

September 29th, 10:30am-1pm | Selby Library

Celebrate Selby Public Library's 25th Anniversary! This milestone event promises an unforgettable experience for book lovers and community members alike. Immerse yourself in a special program by Mote Marine, where you'll learn about marine life and conservation efforts. Explore the history of Selby Library with Josh Goodman, Ph.D. and enjoy delightful refreshments while mingling with fellow book enthusiasts. Take guided tours, engage in "make and take" activities, and experience the magic of our pop-up library activities. Stop by for a day filled with literary surprises and celebration!

12) St Armands Craft Festival and Sidewalk Sale

September 30th-October 1st, 10am-5pm | St Armands Circle

If you're in town this September, you won't want to miss the St Armands Craft Festival and Sidewalk Sale. This exciting event brings together artists from all over the country to showcase their talents in a variety of mediums, including sculpture, photography, glass, paintings, ceramics, jewelry, and mixed media. The festival also features a craft marketplace right on the street, where you can find one-of-a-kind handmade treasures.

This festival is also a chance to connect with the artists and crafters themselves. You can meet the creative minds behind the artwork, learn about their inspirations, and even commission a custom piece. It's a truly interactive experience that will leave you feeling inspired and in awe of the talent on display.So, mark your calendar and head over to St Armands Key for a weekend of art, shopping, and community!

13) 35th Annual Fruitville Grove Pumpkin Fest

September 30th-October 1st, 10am-5pm | Fruitville Grove

The 35th Annual Fruitville Grove Pumpkin Fest is a must-visit event for families and pumpkin enthusiasts alike! Running every weekend from September 30th to October 29th, this festival has something for everyone. Admission, as well as access to the petting zoo, playground, live music, and the Torres Family Circus, is completely free. There are also plenty of exciting rides and activities to enjoy, such as pony rides, a rock wall, bounce houses, zip line, and pumpkin painting.

There is a $5 parking fee, but the fun-filled day is well worth it. Don't miss out on daily activities like the Food Truck Rally, Craft Show, Live Music, Kids Fun Zone, and the opportunity to hold a skunk. Kids can also enjoy pony rides, a mini train ride, hay rides, and even get a hug from a goat. Explore the Wildflower Maze, have an enchanting encounter with a unicorn, and immerse yourself in the beauty of the butterfly garden.

Plus, make sure to catch the Horse Drawn Carriage Rides. Each Saturday at 2:00 pm, there is a Children's Costume Contest where kids can show off their Halloween creativity. And don't forget the daily showtimes of the Torres Family Circus and Extreme Riders at 12:00 pm and 3:00 pm each weekend. The 35th Annual Fruitville Grove Pumpkin Fest promises a fun-filled autumn adventure for the whole family!

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As September comes to a close in Sarasota, it's clear that this month has been filled with endless fun and excitement. From live music to outdoor adventures, there was something for everyone to enjoy. Whether you're a local or a tourist, the events and activities in Sarasota this September have left lasting memories and a desire for more.

As the season changes and we head into fall, let's take a moment to reflect on the amazing experiences we had and look forward to what the next month has in store. Thank you for joining us on this journey of discovery and fun in Sarasota this September. Until next time, keep exploring and falling into fun in this beautiful city!