Whether you're seeking an excuse to enjoy Sarasota's breezy fall weather or looking for a seasonal deal at one of our local attractions, we've got you covered in our Fall Events Guide for 2019. Check out everything you can do outside of regular holiday festivities during the months of September, October and November.

September

Sailing Regatta

September 1; Sarasota Sailing Squadron

The Sarasota Sailing Squadron will host its 72nd Annual Labor Day Regatta, drawing over 100 competitive sailors from across North America. Viewing is free from 8 a.m. to 4 p.m. for spectators at City Island, 1717 Ken Thompson Parkway.

Englewood Pioneer Days

September 1 – 2; Dearborn Street

Englewood's 63rd annual Pioneer Days — a two-week event that kicks off in August — celebrates its grand finale on Labor Day weekend. The Pioneer Days festival takes place from 12 to 8 p.m. at Pioneer Park on Sunday and is followed on Monday by the Labor Day Parade (starting at 9 a.m. on Dearborn Street at St. Raphael's Church). Visit the Englewood Pioneer Days website for a complete schedule of events.

Succulent Sale

September 2; Sarasota Succulent Society

The Sarasota Succulent Society's annual Labor Day sale takes place from 9 a.m. to 1 p.m. at the Succulent Society's historic 1930s house and nursery at 1310 38th St., Sarasota. This is one of just four sales the society hosts annually, so don't miss the rare opportunity to scoop up some succulents!

Ringling Underground Concert Series

Every First Thursday from Sept. 5 – Nov. 7; The Ringling

The Ringling Underground transforms The Ringling museum courtyard into a hip, contemporary art and concert venue the first Thursday of the month from September through November. Select galleries in the museum remain open after-hours until 11 p.m. while regional bands and up-and-coming artists are featured in the courtyard.

$7 Saturdays at Mote Aquarium

Every Saturday from September 7 – 28; Mote Marine Laboratory & Aquarium

It's $7 Saturday at Mote Aquarium! Florida residents receive a whale of a deal with reduced-price admission every Saturday in September, valid for up to four people per group. Without the discount, regular admission is $24 for adults and $18 for kids under 13.

Free State Park Visit

September 7; Oscar Scherer State Park

Celebrate International Literacy Day by bringing a book to Literacy Under the Trees at Oscar Scherer State Park. The event takes place from 10 a.m. to 1 p.m., and park entrance fees will be waived for guests who bring a gently-used book to donate or show their library card.

Spooky History Tour

Sept. 13 & Oct. 11; Historic Spanish Point

Every Friday that falls closest to the full moon through October, Historic Spanish Point hosts a spooky storytelling tour that explores the site's history – from the prehistoric burial mounds of its indigenous people to the 19th century pioneer cemetery. Check for times and purchase tickets ($20 per person) online before the tours sell out.

Free Museum Admission

September 21; The Ringling

Celebrate Smithsonian Museum Day at The Ringling with free admission all day to the art galleries and circus museums.

A Taste of Downtown

September 21; Sarasota Opera House

The Sarasota Opera House is host to the 6th annual A Taste of Downtown, a fundraiser for the Youth Opera, who will perform during the event. Enjoy wine and menu tastings from downtown Sarasota's top restaurants. Tickets are $75 per person.

Venice Beach Party

September 28; Venice Public Beach

Celebrate the end of summer at the 4th annual Venice Beach Party, taking place from 2:30 to 8 p.m. with live music, food and drink vendors, children's activities, and more.

Mystical Bazaar

September 28 – 29; Sarasota Municipal Auditorium

The 2019 Mystical Bazaar takes place from 11 a.m. to 6 p.m. at the Sarasota Municipal Auditorium. For $5 admission, get access to a metaphysical marketplace hosting gemstone and jewelry vendors, psychic readers, healers, fortune tellers, and more.

October

Phillippi Market Returns

October 2; Phillippi Estate Park

Fresh fall fruits and veggies have arrived! The Phillippi Farmhouse Market kicks off its season on Oct. 2, and takes place weekly on Wednesdays at 5500 S. Tamiami Trail, Sarasota, through the month of April.

Craft Festival

October 5 – 6; Central Ave., Sarasota

The 25th Annual Downtown Sarasota Craft Festival takes place in the streets of downtown Sarasota at Central Ave., featuring an array of affordable ceramics, jewelry, stained glass, metal works, and other crafts.

Hungarian Festival

October 12 – 13; Sarasota County Fairgrounds

The 13th annual Hungarian Festival starts Saturday from 10 a.m. to 9 p.m., followed by an after-hours dance party. The festival resumes on Sunday from 12 to 8 p.m. and features live Hungarian music, dance, food and activities for the whole family.

Eat Local Week

Multiple dates from Oct. 17 to Nov. 2; multiple locations

Transition Sarasota’s Eat Local Week is an annual celebration of the best local food and farming in Sarasota and Manatee Counties. Every year, dozens of local partners come together to offer events like Big Mama’s Collard Green Festival, farm-to-fork dinners, workshops and hands-on activities like cooking and gardening workshops. The theme in 2019 is “Exploring Food Waste.” Events will explain food waste, why it matters and how communities can work towards solutions!

Oktoberfest

October 18 – 20; JD Hamel Park

Break out your lederhosen and an appetite for carbs, because beer and pretzels are abundant at Sarasota Oktoberfest, taking place at JD Hamel Park from 10 a.m. to 8 p.m. on Saturday and 10 a.m. to 6 p.m. on Sunday. The Humane Society mobile adoption center will be on site for some extra cuddles.

Sarasota Half Marathon

October 19-20; Van Wezel Performing Arts Hall

Put your running skills to the test during The First Watch Sarasota Half Marathon, Relay & 10K Race Weekend. Enjoy breathtaking views of Sarasota Bay as you cross the John Ringling Bridge before traversing through Sarasota’s stunning neighborhoods and historic sites such as St. Armand’s Circle, Downtown Sarasota and the Ringling Museum of Art. Feel free to choose your own challenge with a 10K and 5K (new in 2019) if 13 miles is too much. Cross the finish line and refuel at the gourmet breakfast buffet from First Watch in addition to a bayside beer garden and live music. For more information and registration, go to the event website.

Venice Sun Fiesta

October 18 – 20; Centennial Park

The Women's Sertoma Club of Venice, FL hosts their Sun Fiesta each year to celebrate the end of summer. The three-day event features a 5K run, “bed races,” arts and crafts vendors, food vendors, the Miss Sun Fiesta, live music, and more. Check schedule for weekend hours.and dancing.

Gospel Experience

October 18, 19 & 26; multiple locations

Oct. 18, 19, 26: The Westcoast Black Theatre Troupe, in collaboration with Key Chorale, explores the rich tradition of black gospel music in American culture with American Roots: The Gospel Experience. The show will take place on three dates, at three locations throughout Sarasota County.

Tour De North Port

October 20; The Imagine School, Upper Campus

The 10th annual Tour De North Port bicycle ride is a great way to take in the sights through some of the most beautiful outdoor settings Florida has to offer. Cyclists are encouraged to ride at their leisure (this is not a race) along on-road routes that stretch across 15, 35 or 65-mile sections of Florida's unique, indigenous pine flatwoods.

November

Birding Season Begins

November 1; Celery Fields

Birding season officially begins in Sarasota County in November, coinciding with the cooler autumn weather in Southwest Florida. The Sarasota Audubon Society opens its doors at Celery Fields with bird naturalist volunteers ready and waiting daily on the park boardwalks from 8:30 a.m. - 10:30 a.m. from November through April to nurture passion in birding fans of all ages. Check the SAS calendar for field trips and activities taking place during the fall and winter months.

Island Car Show

November 2; St. Armands Circle

The 18th annual Ferraris on the Circle showcase at St. Armands Circle draws the more than 75 owners of the sleek Italian sports cars to the Circle to compete for the top prize. The show takes place from 10 a.m. to 4 p.m. at Circle Park.

Jerry Garcia Day

November 3; Fogartyville

Sarasota's community radio station, WSLR, traditionally times its Very Merry Jerry Day celebration in early August to coincide with the Grateful Dead's legendary front man, Jerry Garcia's, August 1 birthday. In an effort to beat the summer heat, the 11th annual Very Merry Jerry Day was moved to November — and Sarasota's all-day jam-fest just got cooler than ever.

Sarasota MOD Weekend

November 8 - 10; multiple locations

Did you know sleepy Sarasota was part of a mid-century modern architecture renaissance following World War II? The Sarasota Architectural Foundation hosts a weekend of tours, art exhibitions, film screenings and lectures about the area’s design influence and legacy. The theme of the 6^th annual celebration will be Sarasota in the Sixties.

Food and Wine Fest

November 9; Premier Sports Campus

Foodies, mark your calendars for the Suncoast Food and Wine Fest, taking place at the Lakewood Ranch Premier Sports Campus. The festival, which supports charities in Sarasota and Manatee Counties, is hosted by the Rotary Club of Lakewood Ranch.

Medieval Fair

Every weekend from Nov. 9 - Dec. 1; Sarasota Fairgrounds

Munch on a roasted turkey leg while you enjoy jousting, combat, chess, medieval-themed comedy acts, Highland bagpipes, aerial shows, the artisan marketplace, and more at the Sarasota Medieval Fair.

Art Festival

November 9 – 10; St. Armands Circle

The 31st annual St. Armands Circle Arts Festival runs from 10 a.m. to 5 p.m. on Saturday and Sunday on the Circle, with work for sale by more than 100 artists across several mediums like painting, photography, sculpting, jewelry, glasswork, and more.

Chalk Festival

November 15-18; Venice Airport Festival Grounds

The Sarasota Chalk Festival returns to the Venice Airport Festival Grounds for its fall installment, themed "Garden of Wonders: a tribute to the marvels of the natural world and the human imagination." Experience chalk fest favorites like the Pavement Music Festival and the real-time creation of awe-inspiring 3D works and optical illusions by street artists from across the globe. Veterans receive free admission on Nov. 18.

Siesta Key Crystal Classic

November 15 – 18; Siesta Key Beach

International sand sculptors gather for the Siesta Key Crystal Classic, where they transform the powdery white sands of Siesta Key into magnificent, marble-like statues on the beach. Enjoy the art — or try your own hand at sculpting during at one of the onsite classes.

Season The Bay

November 16; Sarasota Municipal Auditorium

Experience the tastiest show on Sarasota Bay! Doors open from 11 a.m. to 7 p.m. for guests to sample and shop spices, sauces and other seasonings made by unique local vendors. From barbecue to Bloody Mary mix, this show has a flavor for everyone!

Englewood Beach Waterfest

November 23 – 24; Englewood Public Beach

The Englewood Beach Waterfest makes a splash every November with fun, marine-themed activities for everyone in the family. With exhibitions ranging from powerboat races to marine wildlife education exhibits, this festival showcases everything Florida's Gulf Coast has to offer.