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Festivals to Attend in Sarasota’s Sunny Fall Months
Posted by Best Western Siesta Key onSeptember 20, 2019 in Events, Things To Do.

Fall is one of the best times of the year to be in Sarasota! The temperature begins to drop (only slightly, but it’s enough), colors begin to change (in license plates, that is), and there are a plethora of festivals to attend from art to sandcastles to pumpkins and even Hungarian dance. The best part? Best Western Siesta Key is centrally located in Sarasota so you can easily attend them all.
Here’s a list of Sarasota’s Best Fall Festivals:
September 2019
Saturday, 9/21 – Free Fall Festival
Hosted by NextHome Excellence, this annual festival is held at the Florida Farm Bureau and features carnival games, face painting, bounce houses, live music, and more. Proceeds from beer sales benefit Heroes Welcome Home. (7289 Palmer Blvd, Sarasota, 12pm-5pm, free admission).
October 2019
Saturday, 10/5 & Sunday 10/6 – Downtown Sarasota Craft Festival
This popular craft festival features ceramics, photography, jewelry, painting, clothing. Plus, the Green Market has exotic flora, plants, orchids, handmade soaps, and more. (5 Points and Central Ave., Sarasota, Sat. & Sun. 10am – 5pm, free admission).
Saturday, 10/5 – Fruitville Grove Pumpkin Fest
Fall fun under the shade of large oak trees, the 31st annual Pumpkin Fest features plenty of fun activities for all ages. There’s plenty of food and one-of-kind crafts tool. (7410 Fruitville Rd., Sarasota, every weekend in October, 10am – 5pm).
Saturday, 10/5 – Sarasota Pirates & Rum Festival
Get your pirate costume on and bring your friends for a party like no other that promotes cancer awareness. Enjoy great live music, fantastic food, rum from around the world, and, of course, pirates at the beautiful Van Wezel Bayfront! (777 N. Tamiami Trail, Sarasota, 5pm – 12am, admission $20).
Saturday, 10/5 – Water Lantern Festival
Experience the magic of thousands of floating lanterns on the water during this family friendly event. Create your own design and message and set your lantern alight on the water in an event you’re not likely to forget. (Nathan Benderson Park, 5851 Nathan Benderson Cir, Sarasota, 4pm – 9pm, ticket required).
Saturday, 10/12 & Sunday, 10/13 – 13th Annual Hungarian Festival
It’s the biggest Hungarian festival in Florida. Enjoy Hungarian cuisine and wines and experience live Hungarian music and dance performance. There will also be plenty of activities for the kids as well as a cooking competition and arts and crafts. (Sarasota County Fairgrounds, 3000 Ringling Blvd., Sarasota, Sat. 11am – 10pm, Sun. 11am – 8pm, admission $13 – $18).
Friday, 10/18 – Sunday, 10/20 – Sarasota Oktoberfest
The second annual Sarasota Oktoberfest brings an authentic Oktoberfest experience to downtown Sarasota. There will be plenty of mouthwatering food, big pints of beer, arts, crafts, and live music. (JD Hamel Park at Gulfstream and Main Street, Sarasota, Fri. 4pm – 10pm, Sat. 11am – 10 pm, Sun. 11am – 6pm, free admission).
November 2019
Saturday, 11/9 & Sunday 11/10 – St. Armands Circle Art Festival
For 31 years, St. Armand’s Circle has hosted an art festival showcase original and creative fine art. This year, over 200 artists will descend upon Sarasota offering a broad spectrum of art selections such as sculpture, painting, glass, ceramics, jewelry, mixed media, and more. (411 St. Armand’s Circle, Sarasota, Sat. & Sun. 10am – 5pm, free admission).
Friday 11/15 & Saturday 11/16 – Giving Hunger the Blues Music Festival
Benefitting the Mayors Feed the Hungry program, this year’s theme celebrates the music of Woodstock with Hendrix by Hendrix as the headlining act. Other national and local bands will also perform music from other rock legends that participated in the original Woodstock 50 years ago. (Sarasota Polo Grounds, 8201 Polo Club Lane, Sarasota, Fri. 5:30pm – 9pm, free, Sat. 11:30am – 9:30pm, admission $10 – $20).
Friday, 11/15 – Monday, 11/18 – International Chalk Festival
Street artists from across the globe create awe-inspiring 3-dimensional chalk art. The theme of this installment is “Garden of Wonders,” which pays tribute to the beautiful marvels of the natural world and human imagination. (Venice Airport Festival Grounds, 675 Airport Ave. E.., Venice, Fri. – Sun., 8am – 6pm, veterans and children under 12 free).
Friday, 11/15 – Monday, 11/18 – Siesta Key Crystal Classic International Sand Sculpting Festival
This Master Sand Sculpting competition features 24 international artists creating masterpieces out of sand. Winners are revealed Sunday afternoon, but there’s live entertainment and activities for kids all four days. (Siesta Key Beach, 948 Beach Rd., Siesta Key, Fri. & Mon. 10am – 5pm, Sat. & Sun. 10am – 9pm, admission $5 – $10).
Saturday, 11/16 & Sunday, 11/17 – Sarasota Fall Fine Art Festival
Prestigious artists from all over the U.S. come to this festival to feature their high-quality, original, handmade art which includes painting, ceramics, woodworking, mixed media, photography, jewelry and more. (JD Hamel Park, 199 Bayfront Dr., Sarasota, Sat., & Sun. 10am – 5pm, free admission).
There’s plenty to do in Sarasota to fill up your calendar for fall. Plus, this is the perfect time of year to visit the area’s great beaches. The exceptional autumn sunsets will take your breath away.
For more events and activities happening this fall in the Siesta Key/Sarasota area, visit here.
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