Top Sarasota Events in October

9 Sarasota Events in October You Won’t Want to Miss

Here in Florida, October embodies kind of a sweet spot: the bustle of the holiday season has yet to begin, and the weather gets a little cooler. Sarasota County’s Gulf breezes are perfectly mild in October, and fun events, many of them open-air – are happening every single weekend. Here’s a rundown of some of our favorite Sarasota-area happenings in October.
  1. The Orchid Show 2021: Aerialists from the Tree Top to the Big Top! – Oct. 9
    This breathtaking spectacle takes place among Selby Botanical Gardens’ loftiest treetops and combines two enduring symbols of Sarasota’s legacy: vibrant orchids and circus performers. Watch aerialists perform mind-blowing feats among a canopy teeming with brilliant blooms. 
    10 am–5 pm
    $20; Selby Botanical Gardens’ Downtown Sarasota Campus
  2. Noche Cubana Dance Party with Cimafunk, Oct. 15
    There’s nothing like a dance party to spice up your weekend. A rising star in the Latin music scene, Cuban-born artist Cimafunk brings a unique sound that melds Cuba’s most beloved musical traditions with funk and African rhythms. New York-based DJ Edgaro opens and closes the night, and admission includes a free salsa dance lesson with Kary and Dario of Sarasota-based DK Dance. There’ll also be delectable Cuban food and cocktails. Learn more.
    7 pm
    $35; Ringling Courtyard
  3. Rocktoberfest – Oct. 15-17
    You can’t go through the entire season without attending at least one Oktoberfest-adjacent celebration. This one, as you can tell by the name, brings together tons of bands, including Triggerfish, Kettle of Fish, Ari & the Alibis and others for multi-day jam session. If it’s that oompah sound that puts a little pep in your step, keep an eye out for Bavarian-inspired acts like Alpine Doc and Tahja. Expect large containers of beer and decadent German eats. 
    Friday, 4-10 pm; Saturday 11 am–10 pm; Sunday, 11 am–6 pm
    Free; JD Hamel Park
  4. Falling for Vintage, Oct. 16-17
    Do you describe your style as something you curate? Or search the world over for vintage clothing and décor pieces that are rare and unique? Then this American Vintage Markets event is for you. It brings together vendors who are just as particular as you are when it comes to vintage style – whether it be delicately restored clothing items, handcrafted goods and upcycled accessories. 
    Saturday, 10 am–5 pm; Sunday, 11 am–4 pm
    $8; Robarts Arena
  5. Florida Inline Skating Marathon and 5k Run – Oct. 17
    There’s no backdrop for endurance events that’s quite like lovely Nathan Benderson Park. And the weather’s bound to be just right for this thrilling event – whether you’re spectating or participating. Skating enthusiasts can compete in events of varying lengths –from a 10k jaunt to a full marathon. There’s also a 5k run on the park’s inner loop if wheels aren’t your thing. Learn more.
    7 am–2 pm
    Prices vary; Nathan Benderson Park
  6. Pride in the Park – Oct. 23
    Don your finest rainbow attire and come celebrate LGBTQ+ Pride on the water with Sarasota Pride. The weather is likely to be amazing and the crowd will be lively and fun. Check out local vendors and savor food and entertainment while you’re at it. 
    12-6 pm
    Free; JD Hamel Park 
  7. An Evening with The Pure Led Zeppelin Experience – Oct. 23
    Get the Led out with an electric performance paying tribute to a most legendary band. Marvel as the guys nail some of Zeppelin’s most intricate flourishes, from Bonham’s toughest fills to Page’s most mind-bending licks. Will they play “Stairway”? There’s only one way to find out.
    7 pm
    Admission TBD; Shriners Hall, Sarasota
  8. Fall Festival at UTC – Oct. 23 & 24
    Get into the fall spirit with a pumpkin patch, a trunk or treat and a pet costume contest at this family-friendly event in the back parking lot at University Town Center. Kids and kids at heart will love the carnival rides and games, while grown-ups can savor ale at the beer garden as live bands play. 
    Saturday & Sunday, 11 am–6 pm
    Free; University Town Center
  9. Giving Hunger the Blues – Oct.  31
    Get your groove on – and for a good cause! – at this two-day, event, back from its 2020 hiatus, and is now taking place in beautiful Nathan Benderson Park. Check out local bands at this award-winning, family-friendly event benefiting the Mayors’ Feed the Hungry Program. Food and drink vendors will be on site to help you fuel your fun. 
    11:30 am–9:30 pm
    Tickets start at $15; Nathan Benderson Park