- December 5, 2025
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‘The Legend of Sleepy Hollow’
6 p.m. at Sarasota Polo Club, 8201 Polo Club Lane
$25
Visit ThePlayers.org.
The Sarasota Players returns to the Sarasota Polo Grounds for what has become a local tradition, its family-friendly adaptation of Washington Irving’s “The Legend of Sleepy Hollow.” You’ll see the awkward schoolmaster Ichabod Crane, the farm girl Katrina whose affections he is vying for with Brom Bones and of course, the Headless Horseman on a real horse. Audience members should bring their own chairs and blankets for this not-to-be-missed outdoor event. There will be a costume contest a half-hour before each show. Photos with the HH (as he is known to his familiars) will take place after the performance. Runs through Oct. 25.
Hermitage Sunsets @ Selby Gardens
6 p.m. at Marie Selby Botanical Gardens, 1534 Mound St.
Free
Visit HermitageArtistRetreat.org.
Hermitage Artist Retreat presents a conversation led by Hermitage Artistic Director and CEO Andy Sandberg that features a performance by violist Ralph Harris.
‘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 Nate Jacobs, “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.
‘Feeling Good’
7:30 p.m. at Florida Studio Theatre’s Court Cabaret, 1265 First St.
$18-$42
Visit FloridaStudioTheatre.org.
The latest musical revue created by Rebecca Hopkins and Richard Hopkins, “Feeling Good” pays tribute to singers some call contemporary crooners, artists like Michael Bublé and Bette Midler. A dynamic trio — Haley K. Clay, Andrew Leggieri and Russell Mernagh — makes its Florida Studio Theatre debut. By performing swingin’ hits like “Come Fly With Me,” “It Had to Be You” and “Me and Mrs. Jones,” “Feeling Good” reminds us that seduction works best with a little savoir faire. Runs through Feb. 8.
‘Hello, Dolly’
7:30 p.m. at Manatee Performing Arts Center, 502 Third Ave. W., Bradenton
$31.50
Visit ManateePerformingArtsCenter.com.
The Manatee Players community theater presents its production of the feel-good musical that follows a tireless matchmaker Dolly Gallagher Levi, a role originated by Ethel Merman, as she tries to find a wife for the tightisted Horace Vandergelder. Set in 1890s New York, “Hello, Dolly” is a timeless story that celebrates second chances and living a grand life. Runs through Nov. 2.
‘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.
Haunted Trail at Arlington Park
5-7 p.m. at Arlington Park & Aquatic Complex, 2650 Waldemere St.
Free
Visit SarasotaFL.gov.
Enjoy games and trick-or-treating at this haunted trail carnival, held along Arlington Park's half-mile walking trail. Children under 5 must be accompanied by an adult.
BooFest
6-9 p.m. at Main Street at Lakewood Ranch
Free
Visit LakewoodRanch.com.
BooFest, presented by Veteran Air, returns to provide an evening of family fun. Children in their costumes are invited to trick-or-treat along a street filled with vendor booths and merchants handing out sweet treats. A Kids Zone, presented by Grace Community Church, includes face painting, balloon twisting, inflatables, and more. The main stage will include Music Compound entertainers at 6 p.m., the Mad Scientist's interactive science show at 7 p.m. and a magic show at 8 p.m.
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.
‘Star Wars: The Empire Strikes Back’
7:30 p.m. at Van Wezel Performing Arts Hall, 777 N. Tamiami Trail
$50-$100
Visit SarasotaOrchestra.org.
Dinner and a movie? How about a live orchestra and a movie? Led by guest conductor Connor Gray Covington, the Sarasota Orchestra plays John Williams’ score as “Star Wars: The Empire Strikes Back” unspools on the big screen at the Van Wezel Performing Arts Hall. Runs through Oct. 25.
Program One: ‘Intrinsic’
7:30 p.m. at FSU Center for the Performing Arts, 5555 N. Tamiami Trail
$35-$125
Visit SarasotaBallet.org.
The Sarasota Ballet kicks off its 2025-26 season with a trio of performances. Leading Program One is Michel Fokine’s “Les Sylphides,” honoring the 100th anniversary of Dame Alicia Markova joining The Ballet Russes. Next up is “The Lorenz Butterfly,” Jessica Lang’s world premiere that the Ballet first performed at Jacob’s Pillow dance festival in July. It is set against a backdrop of Lang’s paintings exploring color and change. Will Tuckett’s “Changing Light,” a commission that is a love letter to Sarasota, closes the evening. Runs through Oct. 26.
Learn from 'The Bird Lady'
10:30-11:30 a.m. at Save Our Seabirds, 1708 Ken Thompson Parkway, City Island
Free
Visit SaveOurSeabirds.org
Longtime volunteer and bird lover Mattie Watson is presenting on Florida's wading birds. Session two on raptors takes place Nov. 8, and session three on backyard birds and waterfowl takes place Nov. 22.
Gulfcoast Pride Festival
Noon to 5 p.m. at Overtown Square Park, 1386 Boulevard of the Arts
Free
Visit SarasotaFL.gov.
Sarasota’s largest Pride Festival features over 100 vendors, live performances from local and international entertainers, and food from Sarasota's top local restaurants.
Water Lantern Festival
4 p.m. at Nathan Benderson Park, 5851 Nathan Benderson Circle
$38 in advance; $58 day-of
Visit WaterLanternFestival.com.
Enjoy the magic of hundreds of lanterns lighting up the lake at Nathan Benderson Park. Food trucks and live music start at 4 p.m., and at 6:30 p.m. you can design your own eco-friendly lantern. Lanterns launch at 7 p.m.
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 that is 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.
Taste of The Bay
Noon to 3 p.m. at The Oval Parking Lot, 1055 Boulevard of the Arts
Free
Visit TheBaySarasota.org.
Taste some of Sarasota's popular locally-owned restaurants at this outdoor food festival hosted in partnership with the Sarasota-Manatee Originals and featuring live music by The Rockefellers. Five food tickets for $5, purchasable at event. Most food items range between three and five tickets.
Pet Blessing
1 p.m. at All Angels by the Sea Episcopal Church, 563 Bay Isles Road, Longboat Key
Free
Visit AllAngelsLBK.org.
Bring your furry, feathered or scaly friends for a special blessing of the pets.
Haunted Illusions
7 p.m. at Van Wezel Performing Arts Hall, 777 N. Tamiami Trail,
$36 and up
Visit VanWezel.org.
Be prepared to be dazzled by master illusionist David Caserta — seen on “America’s Got Talent” and “Penn and Teller: Fool Us” — as he performs never-before-seen tricks and combines comedy and audience participation with his sleight of hand. Audience members are encouraged to dress up in Halloween costumes and participate in a costume contest that involves social media and the hashtag #VanWezelHalloween.
Monday Night Jazz: James Suggs and Friends
7:30 p.m. at Florida Studio Theatre’s Court Cabaret, 1265 First St.
$34-$39
Visit JazzClubSarasota.org.
Jazz Club of Sarasota presents James Suggs, one of the finest trumpet players in the Bay area, and his ensemble. Suggs has performed tribute shows to Louis Armstrong, Miles Davis and Harry James, and has released a critically acclaimed CD, “You’re Gonna Hear From Me.” Doors open at 6:30 p.m. for food and beverage service.
‘Tangled Whispers’
7:30 p.m. at First Congregational Church, 1031 S. Euclid Ave.
$30
Visit EnSRQ.org.
Contemporary classical music group ensembleNewSRQ opens its 10th anniversary season with a program that includes Sebastian Currier’s “Whispers,” which explores a world where silence can be as expressive as sound. Also on the bill are Amy Williams’ newly commissioned “Tangled Madrigal” for string quartet, Jerod Tate’s “Inchokkilliss” for guitar and percussion and Elliott Carter’s “Triple Duo.”
‘Art Deco: The Golden Age of Illustration’
10 a.m. at the Sarasota Art Museum campus of Ringling College, 1001 S. Tamiami Trail
Free for museum members; $20
Visit SarasotaArtMuseum.org.
The Sarasota Art Museum celebrates the 100th anniversary of the exposition that kicked off the Art Deco movement. More than 100 eye-catching posters from the Crouse Collection as well as industrial furniture, home furnishings and other objects loaned by the Wilsonian-Florida International University are on display. In addition to consumer products, there are posters for automobiles, train and ocean travel, as well as sports competitions that reflected a growing love of speed and luxury in spite of the Great Depression. Through March 29, 2026.
Trick or Treat on the Lake
5:30-8 p.m. at Nathan Benderson Park, 5851 Nathan Benderson Circle
Free
Visit NathanBendersonPark.org.
Celebrate Halloween at Nathan Benderson Park, 5851 Nathan Benderson Circle, Sarasota, with its annual Trick or Treat on the Lake. Come dressed in Halloween costumes for an evening of trick-or-treating along a candy trail decorated by community organizations.
Rafael Ramírez: Chronicle of a Time Was
11 a.m. at The Ringling’s Historic Asolo Theater, 5401 Bay Shore Road
$40-$50
Visit Ringling.org.
In this Art of Performance program in The Ringling’s Historic Asolo Theater, Rafael Ramírez honors flamenco dance and film sensation Antonio Gades on the 20th anniversary of his death. In “Chronicle of a time was,” Ramírez uses key moments in Gades’ life to explore his courage and creative vision. Runs through Oct. 31.
Trunk or Treat
5-8 p.m. at Robert L. Taylor Community Complex, 1845 34th St.
Free
Visit LetsPlaySarasota.com.
Enjoy a family-friendly evening featuring games, candy, and a contest for costumes and best trunk decorations.
A Haunting Night
7:30 p.m. at The Island Players, 10009 Gulf Drive, Anna Maria
$15
Visit TheIslandPlayers.org.
The staff of the Island Players claims that their little community theater is haunted, but we’ll let you be the judge. For one performance only, Mark Shoemaker and Heiko Knipfelberg will read Victorian ghost stories by E.F. Benson. Don’t be surprised if you hear some things that go bump in the night. Costumes are welcome.
