The best things to do in Sarasota, Lakewood Ranch, Longboat for Oct. 16-22


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  • | 10:00 a.m. October 14, 2025
"Twilight in Concert" comes to the Van Wezel Performing Arts Hall Oct. 17.
"Twilight in Concert" comes to the Van Wezel Performing Arts Hall Oct. 17.
Courtesy image
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Thursday, Oct. 16

Strings Con Brio 10th Anniversary Party and Concert
6 p.m. at Venice Community Center, 326 Nokomos Ave. S., Venice
Free
Visit StringsConBrio.org.

Led by Maestro Kenneth Bowermeister, community orchestra Strings Con Brio celebrates its 10th anniversary with a free party and concert. 


The Sarasota Orchestra takes a musical tour of spooky music with Bugs, Bats and Birds from Oct. 16-18.
Courtesy image

Bugs, Bats, and Birds
7:30 p.m. at Holley Hall, 709 N. Tamiami Trail
$48-$69
Visit SarasotaOrchestra.org.

Guest conductor Stuart Chafetz leads the Sarasota Orchestra on a musical tour of spooky music from opera, movies, ballet and rock ‘n’roll. Chafetz is the principal pops conductor of the Columbus Symphony, the Chautauqua and the Marin Symphony. The wide-ranging program opens with the overture to “Die Fledermaus” and ends with a Beatles tribute, with themes from Batman TV shows and movies in between. Runs through Oct. 18. 


‘Heathers the Musical’
7:30 p.m. at Dingbat Theatre Project, 7288 S. Tamiami Trail
$10-$60
Visit DingbatTheatre.org

Luke Manual’s Dingbat Theatre Project leans into the spooky season with “Heathers the Musical,” a dark comedy about a couple of misfits who want to deepsix the troika of girls named Heather who are the Mean Girls of Westerberg High. With book, music and lyrics by Kevin Murphy and Laurence O’Keefe, the musical is based on the R-rated 1989 film of the same name starring Winona Ryder and Christian Slater. It contains references to illicit teen pastimes that give parents nightmares. Runs through Oct. 26.


‘Misery’
7:30 p.m. at Manatee Performing Arts Center, 502 Third Ave. W, Bradenton
$31.50
Visit ManateePerformingArtsCenter.com

What happens when a celebrated author is abducted by his No. 1 fan? Find out during this Manatee Players production of William Goldman’s play, which is based on Stephen King’s best-selling novel of the same name. Runs through Nov. 2. 


Friday, Oct. 17

The Sarasota Jewish Theatre presents "I Never Saw Another Butterfly" from Oct. 17-19.
Photo by Sorcha Augustine

‘I Never Saw Another Butterfly’
3 p.m. at 3501 S. Tamiami Trail, Unit 1130
$25
Visit SarasotaJewishTheatre.com.

Sarasota Jewish Theatre presents “I Never Saw Another Butterfly," a 45-minute adaptation of Celeste Raspanti’s two-act play inspired by artwork created by children at the Terezin Concentration Camp during World War II. SJT Artistic Director Carole Kleinberg describes the play as depicting “the healing power of art in the face of adversity.” Runs through Oct. 19. 


Rocktoberfest
4-10 p.m. at J.D. Hamel Park, 199 Bayfront Drive
Free
Visit SarasotaFL.gov.

Celebrate Oktoberfest at the park with live music, food and drinks, and a shopping area featuring local vendors. Continues 11 a.m. to 10 p.m. Saturday and 11 a.m. to 6 p.m. Sunday.


Sights + Sounds: 'Alice in Wonderland'
6 p.m. at 1560 Lakefront Drive, Waterside Place, Lakewood Ranch
Free
Visit LakewoodRanch.com.

Enjoy the Asolo Rep on Tour production of "Alice in Wonderland" adapted from Lewis Carroll by Asolo Rep's Artistic Associates Cat Brindisi and David Darrow. The show invites the crowd to enjoy the fast-paced play that brings the spectators on an adventure of imagination. 


‘Twilight in Concert’
7 p.m. at Van Wezel Performing Arts Hall, 777 N. Tamiami Trail
$46 and up
Visit VanWezel.org

When it was first released in 2008, the teen vampire romance “Twilight” sparked pandemonium, largely due to the on-screen chemistry and real-life romance between its stars Kristen Stewart and Robert Pattinson. As the young adult novel that inspired the “Twilight” franchise celebrates its 20th anniversary, GEA Live and Lionsgate Films are screening the original film in 60 cities around the country with a live orchestra on stage and hundreds of candles. Groups of 10 or more can call the Van Wezel at 941-263-6726 to arrange seating at this goth extravaganza. 


‘Purlie’
7:30 p.m. at Westcoast Black Theatre Troupe, 1012 N. Orange Ave.
$54 adults, $24 students 25 and under and active military
Visit WestcoastBlackTheatre.org.

Directed by Westcoast Black Theatre Troupe founder and artistic director, “Purlie” is a musical based on Ossie Davis’ Tony-winning play, “Purlie Victorious,” which premiered on Broadway in 1970 and was revived to great acclaim in 2023. In the WBTT production Raleigh Mosely II stars as a Black preacher who returns to his home in the Jim Crow South to save his community church. Sarasota audiences will see such local favorites as Jannie Jones, Chris Caswell, Patric Robinson and Jazzmin Carson as well as WBTT newcomers Cody Farkas and Marcey Green. Runs through Nov. 9. 


Michael Grieve, Sigrid Wise and Brian Ott are A Band Called Honalee, appearing at Florida Studio Theatre's Goldstein Cabaret through Nov. 2.
Photo by Sorcha Augustine


‘A Band Called Honalee’
7:30 p.m. at FST’s Goldstein Cabaret, 1239 Palm Ave.
$39 and up
Visit FloridaStudioTheatre.org.

The subtitle to Florida Studio Theatre’s last cabaret show of the season is “A Tribute to Peter, Paul Mary… and Friends,” but any self-respecting folk rock fan can spot the play on words in the name “A Band Called Honalee.” ICYMI, it refers to the mythical land made famous by the children’s song “Puff the Magic Dragon.” The incarnation of the Band Called Honalee appearing in Sarasota includes Brian Ott, a veteran of FST’s “59th Street Bridge,” Michael Grieve, Geoffrey Neuman and Sigrid Wise. Runs through Nov. 2. 


Richard O’Brien’s ‘The Rocky Horror Show’
7:30 p.m. at Venice Theatre’s Raymond Center, 140 Tampa Ave. W., Venice
$40-$18
Visit VeniceTheatre.org.

Can it really be the 50th anniversary of this timeless classic? Let’s do the “Time Warp” again as Venice Theatre presents the story of Brad and Janet, repressed sweethearts who end up in the spooky mansion of a mad, cross-dressing scientist after they get a flat tire. Cosplay and audience interaction is encouraged. Runs through Oct. 25.


Saturday, Oct. 18

Main Street Market
10 a.m. to 2 p.m. at 8141 Lakewood Main St.
Free
Visit MainStreetMarketLWR.com.

Visit Lakewood Main Street to shop from dozens of vendors featuring local art, jewelry, retail, food, plants and more.


Downtown Sarasota Craft Festival
10 a.m. to 5 p.m. at Selby Five Points Park, 1 Central Ave.
Free
Visit ArtFestival.com.

Explore jewelry, ceramics, photography and clothing and other offerings, as well as a green market featuring handmade soaps, gourmet spices and freshly popped kettle corn. Continues Sunday.


Lakewood Ranch's Stephanie Pufall and her 3-year-old daughter Millie get to know a Dakin Dairy cow at the Harvest Festival.
Photo by Jay Heater

Harvest Festival
10 a.m. to 5 p.m. at Dakin Dairy Farms, 30771 Betts Road, Myakka City
$20; children 5 and under free
Visit DakinDairyFarms.com.

Dakin Dairy Farms Harvest Festival runs every Saturday and Sunday through the end of October. The event includes food trucks, vendors, live music, a kid's zone, pumpkins, a corn maze, and more. The event has free parking. 


St. Armands Fall Fine Art Festival
10 a.m. to 5 p.m. at 434 St. Armands Circle
Free
Visit ParagonFestivals.com.

View the work of artists and artisans from across Florida and the country, including sculpture, jewelry, painting, photography, glass, ceramics, mixed-media, metalwork, fiber art and woodworking. Continues Sunday.

‘Edgar and Emily’ Play Reading
2 p.m. at Tree Fort Productions, 3501 S. Tamiami Trail, Suite 136
$25
Visit TreeFortProductionsProjects.com

Katherine Michelle Tanner’s Tree Fort Productions Projects presents Joseph McDonough’s “Edgar and Emily,” which imagines what would happen if Edgar Allen Poe stepped into the boudoir of Emily Dickinson. The program is presented as part of the Green Leaf Play Reading Series.


FST Improv: ‘We’re Doomed!’
7:30 p.m. at Florida Studio Theatre’s Bowne’s Lab, 1265 First St.
$15-$18
Visit FloridaStudioTheatre.org

‘Tis the spooky season, and one way to get some thrills, chills and a few laughs at the same time is with an original horror movie created by FST Improv performers with audience input. As the action unfolds, you decide whether to press “rewind,” “fast forward” or “play” on this never-before-seen production. Runs Saturdays through Oct. 25. 


Bijayini Satpathy Indian Classical Dance and Reception
7:30 p.m. at The Ringling’s Historic Asolo Theater, 5401 Bay Shore Road
$100
Visit Ringling.org.

The Ringling opens its Art of Performance season in the museum’s jewelbox Historic Asolo Theater with Bijayini Satpathy’s “Doha." Satpathy developed the program exploring the relationship between prayer and play during a yearlong residency at The Metropolitan Museum of Art. Repeats Oct. 19, when a regular performance costs $40-$50. 


Sunday, Oct. 19

Morton's Firehouse Chili Cookoff
2-5 p.m. on Osprey Avenue between Hyde Park Street and Hillview Avenue
Free admission; tasting tickets $15
Visit Facebook.com.

This community event brings together fire departments, including Sarasota, Cedar Hammock, Venice, Longboat Key, Englewood and North Port, as well as the Sarasota Police Department, to see who can achieve the titles of Best Firehouse Chili and Best Booth. Attendees will able to vote for a people's choice winner. The event, which kicks off with an opening ceremony at 1:45 p.m., will feature live music by The Bootleggers and a kids’ zone. Super Bowl champion David Baas and his family have provided 100 free tasting tickets for first responders, nurses, military members, law enforcement and teachers available at the SRQ Vets tent. All proceeds from the event support the Sarasota Firefighters Benevolent Fund. 


Artist Series Concerts will honor Joseph Holt, the recently retired director of Choral Artists of Sarasota, at its Legacy concert on Sunday, Oct. 19.
Courtesy image

Legacy Concert
4 p.m. at Fischer/Weisenborne Residence, 7459 Cabbage Palm Court,
$70
Visit ArtistSeriesConcerts.org.

Artist Series Concerts salutes Joseph Holt, who recently retired as artistic director of Choral Artists of Sarasota. Holt joins Sarasota Orchestra Concertmaster Daniel Jordan and assistant principal cellist Christopher Schnell in an all-Russian program of Rachmaninoff, Kabalevsky, and Shostakovich. 


Monday, Oct. 20

Jazz Jam SRQ
5:30 p.m. at Selby Library, 1331 First St.
Free
Visit JazzClubSarasota.org.

Sponsored by the Jazz Club of Sarasota, the twice-monthly jazz jam sessions bring people of different skill levels together for an improvised musical session while providing a free performance for those who come to listen.


'Ancestral Edge: Abstraction and Symbolism in the Works of Nine Native American Women Artists'
10 a.m. at The John and Mable Ringling Art Museum, 5401 Bayshore Road
Free with $30 admission; Mondays free
Visit Ringling.org.

Aficionados of Native American art often have to travel to places such as Washington, D.C., Phoenix and Santa Fe to see contemporary work. The Ringling has recently been bringing more visibility to contemporary Native American art, first with its 2023 show, "Reclaiming Home" showcasing members of Florida tribes, and now with "Ancestral Edge" featuring nine female artists from across the U.S. Their bold multimedia works occupy the Keith D. Monda Gallery for Contemporary Art through April 2026.


Tuesday, Oct. 21

Lillian Blades' work, "Sanctuary," is an expansion of a piece displayed in 2024 at the Atlanta Botanical Gardens.
Image courtesy of Ryan Gamma


'Lillian Blades: Through the Veil’
10 a.m. at the Sarasota Art Museum campus of Ringling College,1001 S. Tamiami Trail
Free for museum members; $20
Visit SarasotaArtMuseum.org.

Award-winning artist Lillian Blades invites visitors to get lost in her first solo museum exhibition at Sarasota Art Museum. Her installation of “veils” combines handcrafted and found objects to create a mesmerizing display. Blades attributes her use of dazzling color to her childhood in The Bahamas and her process of creating large-scale assemblages to her late mother, an accomplished seamstress. Runs through Oct. 26.

 

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