Sarasota County Autumnal Event Guide: Fall Festivals and Family Fun

School is back in session and the scent of pumpkin spice is sneaking its way into coffee shops… It must be fall in Sarasota! As the hot-and-humid summer draws to a close, it ushers in a breezier season filled with outdoor events, festivals and family outings. Grab a calendar and plan out your autumn months with Visit Sarasota.

September

As campuses fill up for the new semester at New College and Ringling College of Art + Design, Ringling Underground will launch its fifth fall series at The Ringling museum courtyard. The event, taking place on the first Thursday of the month, September through November, features an eclectic mix of local and regional indie bands and outdoor art exhibitions. Ringling Underground is all-ages friendly event. Admission is $15 at the door—or free to college students presenting a valid school ID.

Labor Day weekend is the traditional herald of summer's end—a time for last-hurrah weekday barbecues and beach trips. In Sarasota, it's also the weekend 70th annual Sarasota Sailing Squadron Regatta. This year, the sailing squadron will host more than 300 competitive sailors from the U.S. and Canada on five separate race-courses open to all ages and classes of sailing vessels. The event includes live music, a barbecue, and awards ceremony.

Also taking place on Labor Day weekend is the Tampa Bay Labor Day Soccer Tournament at the Premier Sports campus in Lakewood Ranch. The event, taking place on Sept. 3-5 at the largest soccer complex in the state, expects 250+ youth teams competing on 30 fields. Admission and parking are free.

The annual Pioneer Days Festival and Parade celebrates the 1896 founding of south Sarasota County's Englewood with a family-friendly festival in the town's Pioneer Park on Dearborn Street on Labor Day weekend. The 60th annual festival includes a car show, kid-friendly activities and events, and a parade.

The Sarasota Succulent Society hosts its annual Labor Day Succulent Sale on Sept. 5. The Labor Day Sale is one of only two annual sales hosted by the Succulent Society, and features bargain prices on plants, as well as an educational program, on the Succulent Society's historic 1938 grounds.

Celebrate International Literacy Day at Literacy Amongst the Trees at Oscar Scherer State Park in Osprey. Admission to this family-oriented event, featuring literary activities and readings, is free with the donation of a gently-used book or upon presentation of a valid library card.

Celebrate Indian culture and cuisine at the Manasota IndiaFest on Sept. 10 at the Bradenton Area Convention Center, located just north of Sarasota in Manatee County. The event features shopping, Indian food, and cultural presentations that feature history and traditional dance, as well as temporary henna tattooing.

On Sept. 10 the Sarasota Opera hosts its 3rd annual Taste of Downtown Food & Wine Festival, a fundraising event for the Sarasota Youth Opera featuring cuisine from top restaurants in the downtown Sarasota area. Purchase tickets online for $65.  

Do your part for the environment by celebrating International Coastal Cleanup Day on Sept. 17 and Oct. 22, and National Public Lands Day on Sept. 24. Event volunteers will team up with the Sarasota County government and parks staff to clean up the coast and remove invasive vegetation from locations in Sarasota, Venice, North Port, Laurel, Nokomis and Englewood.

The first Viva International Latino Festival takes place on Sept. 24 on Main Street in downtown Lakewood Ranch. This street fiesta features international Latin music artists, authentic cuisine, an array of Latin dance presentations, a children's carnival, and arts and crafts vendors from over 50 countries. The festival is in celebration of Latin Heritage Month, taking place Sept. 14 – Oct. 15.

The Sarasota Municipal Auditorium will host the Mystical Bazaar on Sept. 24. The event features a metaphysical market with gems and crystals, jewelry and more, as well as psychic readings, healings, and aura photos. Admission is $5.

Don't forget to bring a beach chair for this party on Venice Public Beach: The Venice Beach Party and Music Festival cools down a Saturday evening on Sept. 24. The party kicks off at 3pm and runs till 8 p.m., featuring live reggae and ska music, local food and beer vendors.

Finally, an excuse to squeeze back into those lederhosen: kick off the Oktoberfest season early with the Oktoberfest Costume Party at Mandeville Beer Garden on Sept. 26. The festival features German beer, of course, paired with German menu items—all to be enjoyed along with the tunes of a live polka band.

October

Prepare to get paleontological at National Fossil Day at the South Florida Museum. This family-friendly free event includes an outdoor fossil dig for kids, a Junior Paleontologist Badge Program hosted by the DeSoto National Memorial Rangers, and fossil exhibitions with professional geologists and paleontologists.

The second annual Beer, Bands and BBQ Festival in Lakewood Ranch takes place on Oct. 1. The event, hosted by The Music Compound music school, features a day of—you guessed it—local craft and domestic beer, music and barbecue-inspired eats. All ages welcome. Tickets are $10 through August 31; $10 at the gate.

The Phillippi Farmhouse Market returns from its summer hiatus for its 8th season opener on Oct. 5. The Market runs from 9 a.m. – 2 p.m. on Wednesdays through April with over 50 vendors of produce, specialty items, and agricultural products.

The month of October is a horticulturist's delight in Sarasota. On Oct. 8 the Sarasota Master Gardeners (a program of University of Florida operated through UF/IFAS Extension) hosts their 11th annual plant sale and sustainable garden education day at Twin Lakes Park at 6700 Clark Road. On Oct. 8-9, the Sarasota Garden Club hosts its GardenFest sale, featuring member-grown Florida friendly plants, educational speakers, and floral demonstrations.

The Beer, Boats and Bacon Festival takes place at Nathan Benderson Park on Oct. 8. This year's festival features live music, over 60 craft beers to sample, bacon dishes from local chefs and restaurants, and a family-friendly 'learn to row' area.  Get presale general admission tickets for $10 and $5 for kids 3-12 online. The beer sampling takes place from 3-7 p.m. for a $30 admission fee.

The Sarasota BMX Track, recently upgraded to become one of the top BMX racing facilities in the world, will host the world's fastest BMX racers at the UCI BMX Supercross World Cup on the weekend of Oct. 8-9. The UCI BMX Supercross World Cup is the world's premier BMX racing series, broadcasted in over 70 countries. Get tickets online.

The annual Ringling International Arts Festival takes place Oct. 13-16 with a tour de force of internationally-acclaimed musicians, dancers and actors. Catch a retelling of Shakespeare's Othello set to a motown theme and other innovative theatre, Australian acrobats, and top composers at this year's festival.

Sarasota prepares for its most vibrant PrideFest, taking place on Oct. 15. Enjoy live music and food, connect with local LGBT organizations, and support LGBT art and crafts vendors at J.D. Hamel Park—located within walking distance of downtown Sarasota and Bay Island Park.

The 10th annual Hungarian Festival celebrates Hungarian culture and heritage at the Sarasota County Fairground on the weekend of Oct. 15-16. The event will host musicians from Hungary representing many genres of music from traditional folk to modern pop, dance performances, archery demonstrations, a goulash cooking competition, Hungarian cuisine, vendors, and a kids corner with carnival games, pony rides and theater performances.

Clowns, acrobats, and animals, oh my! The Sahib Shrine Circus is in town Oct. 28-30. Tickets are $25 for adults and $8 for kids.

Beer returns to Nathan Benderson Park on Oct. 29 for the Sip the Sunshine: All Florida Craft Beer Festival. The festival features Florida craft breweries, including established, award-winning breweries as well as up-and-coming newcomers to the Sunshine State craft beer scene. It will also feature Florida-inspired cuisine to pair with local and statewide brews. Get tickets online.

The 25th anniversary Giving Hunger the Blues Festival takes place on Oct. 30 at the Van Wezel Performing Arts Center. Reverend Barry and the Funktastic Soul featuring the Hellacious Horns headlines this year's festival, which also includes performances by the reggae band Jah Movement, Twinkle and Rock Soul Radio, and RJ Howson. This year's festival supports the Women's Resource Center of Sarasota/Manatee, the Mayor's Feed the Hungry Program, and the Generoso Foundation. Purchase tickets online. 

November

Take in the fall weather at the Bay Preserve in Osprey at the Conservation Foundation of the Gulf Coast's annual Family Fall Festival on November 5. Engage in outdoor fun with tree climbing, hula hoop classes, arts and crafts, water conservation activities, kayaking and dip net fishing at this free family event.

The Sarasota Medieval Fair returns for the weekends of Nov. 5-6, 12-13, and 19-20. Munch on a roasted turkey leg while you enjoy jousting, human combat chess, medieval-themed comedy acts, Highland bagpipes, aerial shows, the artisan marketplace, and more. This year's festival features a new medieval tavern pub crawl. Get tickets online.

The Venice Concert Band will perform a Salute to Veterans in recognition of Veteran's Day on Nov. 7. Tickets will be available for $7 at the Venice Performing Arts Center box office on the evening of the performance.

The annual Chalk Festival takes place at the Venice Airport Nov. 10-13 (UPDATED: 2017). Top international chalk artists create their work over three days of the four-day festival, which also includes an open chalk art zone where visitors can leave their artistic mark, the Pavement Music Festival, and a 5k run. View the finished works of chalk art on the festival's final day.

The 7th annual Siesta Key Crystal Classic takes place Nov. 11-15. Master sand sculptors flock to Sarasota to sculpt masterpieces in the marble-white sand of Siesta Key for the annual competition. Outside the master competition, four amateur competition categories allow all ages to get in on the sculpting action. Make sure to catch the masters' finished products on the 15th—they will be swept away the following day.

The 15th annual Suncoast Food and Wine Festival comes to the Sarasota Polo Club in Lakewood Ranch on Nov. 12, offering a selection of food and wine tastings from the area's top restaurants. To date, the Rotary Club of Lakewood Ranch has raised more $1.3 million for charity through the event.

Nov. 12 brings the 3rd annual SRQ Rocks! Rock for a Cause battle of the bands to downtown Sarasota's Main Street. Local musicians compete in the concert festival for a $1500 cash prize and the chance to allocate $3500 to local music education programs.

The Humane Society of Sarasota County offers another opportunity to give back on Nov. 12 at the 24th Annual Hot Dogs & Cool Cats Laugh Your Paws Off Gala at the Ritz Carlton. This evening of comedy includes a champagne reception and dinner, open bar, and comedy entertainment. HBO-featured standup comedian, film and television star Larry Miller headlines the show. Tickets for this ritzy event are available online.

Continuing the 'Season of Giving' theme, All Faiths Food Bank's annual Bowls of Hope takes place on Nov. 13 at a new location at Ed Smith Stadium. Guests can pick a unique, handcrafted bowl decorated by a local artist to fill with soup, bread and desserts provided by 40 local restaurants—and take the bowl home as a keepsake. Ticket sales ($30 in advance, available online for adults and $10 for children) support the All Faith's Food Bank.

The 4th annual Venice Blues Festival takes place on Nov. 19. This year's lineup includes Lazy Lester, Chris Thomas King, Doug Deming and the Jewel Tones, Lisa Ridings Band, and Robert "Lefty Preacher" Sampson. Purchase tickets online.

Get Gatsby-esque at Lindy on the Lawn at Historic Spanish Point on Nov. 19. This Roaring Twenties-themed jazz festival on the Little Sarasota Bay-side lawn of Historic Spanish Point takes place from 11 a.m. – 5 p.m. The event features music from Michael Arenella & the Dreamland Orchestra, a 'hot-dance' style 1920s-early 1930s 'jazz orchestra.'

The Mustang Club of West Central Florida will hold the 25th annual Ponies Under the Palms Mustang and Ford Show on Nov. 20, where Ford enthusiasts from around the region will show their new model and antique Mustangs in an awards competition. Event registration proceeds benefit the Southeastern Guide Dogs and Take Stock in Children. Visitors attend for free.