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The best things to do in Sarasota, Lakewood Ranch, Longboat for Oct. 26 to Nov. 1


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  • | 11:00 a.m. October 24, 2023
The Headless Horseman (Carmen Hansen) was the highlight of the 2022 performance of "The Legend of Sleepy Hollow."
The Headless Horseman (Carmen Hansen) was the highlight of the 2022 performance of "The Legend of Sleepy Hollow."
Photo by Ian Swaby
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Thursday, Oct. 26

Trick or Treat on the Lake
5:30-8 p.m. at Nathan Benderson Park, 5851 Nathan Benderson Circle
Free
Visit NathanBendersonPark.org.

Trick or Treat on the Lake is a free Halloween event (parking is $10) that is presented by Oak and Stone. Come dressed in Halloween costumes for an evening of trick-or-treating along a candy trail decorated by community organizations. An area will host interactive play, storytelling, live music and a Halloween movie.


‘Red’
7:30 p.m. at The Crossings at Siesta Key, 3501 S. Tamiami Trail
$40
Visit TreeFortProductions.com.

Katherine Michelle Tanner's Tree Fort Productions opens its season with "Red," John Logan's play about the artist Mark Rothko (Lee Gundersheimer), who is challenged by his assistant (Alex Teicheira) about the ethics of a high-profile commission. Runs through Oct. 29. 


"The Rocky Horror Show" runs through Oct. 31 at the Manatee Performing Arts Center.
Courtesy image

'The Rocky Horror Show'
7:30 p.m. at Manatee Performing Arts Center, 502 Third Ave. W., Bradenton
$27; $50 on Halloween
Visit ManateePerformingArtsCenter.com.

Do the “Time Warp” again as the Manatee Players 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. 31.


The Woman in White (Emily Eader) gets up close to the audience during the 2022 "Legend of Sleepy Hollow" performance.
Photo by Ian Swaby

‘The Legend of Sleepy Hollow’
6 p.m. at The Sarasota Polo Club, 8201 Polo Club Lane
$15-$65
Visit ThePlayers.org.

The Players Centre for Performing Arts is presents a family-friendly, spooky, festive play about Ichabod Crane, the object of his affection Katrina, his rival Brom Bones, and one of the most famous ghosts in America, the Headless Horseman. No seating will be provided. Please bring your own lawn chairs and blankets. This is an outdoor event. Runs through Oct. 28.

Andrew Dice Clay
7 p.m. at McCurdy’s Comedy Theatre, 1923 Ringling Blvd.
$123
Visit McCurdysComedy.com.

Comic legend Andrew Dice Clay rose to stardom in the late 1980s and early 1990s with a brash, no-holds-barred style. “The Diceman” was the first comedian to sell out Madison Square Garden. He starred in the film “The Adventures of Ford Fairlane” and has appeared on “Saturday Night Live” and “The Celebrity Apprentice.” His McCurdy’s show includes special guest Eleanor Kerrigan. A second performance will be Oct. 27. 


‘The Drowsy Chaperone’
7:30 p.m. at Manatee Performing Arts Center, 502 Third Ave. W, Bradenton
$30-$38
Visit ManateePerformingArtsCenter.com.

Winner of five Tony Awards, "The Drowsy Chaperone" is a tribute to the Jazz Age musicals. As a theater fan listens to his favorite cast album, the characters come to life in his apartment. Runs through Nov. 5.


Friday, Oct. 27

Jazz at Two: Kevin Celebi
2 p.m. at Unitarian Universalist Church of Sarasota, 3975 Fruitville Road
$15-$20
Visit JazzClubSarasota.org.

The Jazz Club of Sarasota presents Kevin Celebi and his Harmony Sanity Septet, who takes audiences on a tour of jazz cities across the U.S.


‘Siddhartha: A Hermitage Collaboration of Words and Music’ 
6 p.m. at Hermitage Beach, 6660 Manasota Key Road, Englewood
$5
Visit HermitageArtistRetreat.org.

Herman Hesse's "Siddhartha" serves as the inspiration for this new collaboration between celebrated poet Melissa Studdard and Grammy Award-winning composer Christopher Theofanidis, both Hermitage Fellows.


Paul, 1-year-old Mya and Leah Baumgert at the 2022 BooFest.
Photo by Jay Heater

BooFest
6-9 p.m. at Main Street at Lakewood Ranch
Free
Visit LakewoodRanch.com.

The annual BooFest event offers family-friendly entertainment, food and drink vendors and children's activities. The event is free. Children should bring their trick-or-treat bags to collect goodies from sponsors and merchants. Many of the children will be dressed in Halloween costumes and a costume parade will be held.


'Star Wars: A New Hope In Concert'
7:30 p.m. at Van Wezel Performing Arts Hall, 777 N. Tamiami Trail
$49-$110
Visit SarasotaOrchestra.org.

May the force be with you as the Sarasota Orchestra performs John Williams’ award-winning score for the inaugural “Star Wars” while the 1977 movie plays on a big screen in the Van Wezel Performing Arts Hall. Susie Seiter, a conductor and orchestrator best known for “The Legend of Zelda: Symphony of the Goddesses,” leads the orchestra. Continues Oct. 28.


'The Rocky Horror Picture Show' screening and party
10 p.m. at Lakewood Ranch Cinema, 10715 Rodeo Drive, Suite 8, Lakewood Ranch
$35
Visit FilmSociety.org.

The ghoulish festivities begin with a costume contest, with the winner receiving a $50 gift card to the Sarasota Film Society. The evening includes BOGO beer and wine specials. Tickets include admission to the film, popcorn, candy and a soft drink. All tickets must be purchased online by 5 p.m. on Oct. 25.

Saturday, Oct. 28

Grayson Tullio, Monika Oberer and Grayson's dog, Panda, head to the finish line of the 2022 Boo Run 5K. They dressed in a "Wizard of Oz" theme.
Photo by Jay Heater

Boo Run
7:30 a.m. at 6300 University Parkway
$40
Visit RunLWR.com/Boo-Run-5k/.

The annual Boo Run is  a fundraiser for Another Day for Gray (Duchenne muscular dystrophy research) and the Humane Society at Lakewood Ranch. A Kids Boo Dash starts at 7:30 a.m., and a 5K run or walk begins at 8 a.m. A 5K run or walk with dogs begins at 8:10 a.m. 


Manasota BUDS Walk
11 a.m. at Bayside Community Church, 15800 State Road 64, Lakewood Ranch
$25
Visit Charity.PledgeIt.org/buddy-walk-2023.

The annual Manasota BUDS walk for Bringing Up Down Syndrome will raise funds to increase awareness of the disease. 


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

Join the cast of FST Improv for an original horror flick just in time for the spooky season. The audience holds the remote control, with the power to rewind, fast forward and press play in this frightful new production.


Halloween Block Party 
6p.m. to midnight at The Gator Club, 1490 Main St.
Free
Visit TheGatorClub.com.

Advertised as the largest block party in Sarasota, this event features live music, costume contests and food trucks. Outside music begins at 8 p.m.


Sunday, Oct. 29

Sarasota Opera Volunteer Fair
1-3 p.m. at Sarasota Opera House, 61 N. Pineapple Ave.
Free
Visit SarasotaOpera.org.

Learn about a variety of behind-the-scenes, onstage and front-of-house volunteer opportunities at this community event, which will also feature backstage tours of the historic Sarasota Opera House and a performance by Sarasota Opera fall resident artists.


Michael Mendez stars in "Harry Belafonte: King of Calypso."
Image courtesy of Sorcha Augustine

'Harry Belafonte: King of Calypso'
7:30 p.m. at Westcoast Black Theatre Troupe, 1012 N. Orange Ave.
$35
Visit WestcoastBlackTheatre.org.

WBTT fan favorite Michael Mendez stars in an original music revue about Harry Belafonte, the barrier-breaking singer, actor and civil rights activist who died earlier this year at age 96. The show includes such iconic Belafonte hits as "Day-O," "Shake Senora" and many more. Continues Oct. 30.


Monday, Oct. 30

'The Phantom of the Opera'
7 p.m. at St. Armands Key Lutheran Church, 40 N. Adams Drive, St. Armands Key
Free
Visit SAKLC.com.

St. Armands Key Lutheran Church has a Halloween treat for classic film lovers: a screening of the 1925 film, “The Phantom of the Opera.” Adam Aceto, the guest artist for the evening, will accompany the movie on the organ. Aceto is the staff organist at Walt Disney World in Orlando, Florida, and is the only full-time organist in the Walt Disney Company. At Disney World’s storied Wedding Pavilion he plays hundreds of weddings and other special events each year. 


Tuesday, Oct. 31

Noah and Tiffany Bond bring the magic to the 2022 Safe Treats event.
Photo by Harry Sayer

Siesta Key Safe Treats
3-6 p.m. at South Village and Siesta Key Village
Free
Visit My.SiestaKeyChamber.com.

Hosted by Siesta Key Chamber of Commerce, this event allows kids to trick-or-treat with different businesses marked by festive balloons. Participating businesses will be open in South Village at the intersection of Stickney Point Road and Midnight Pass Road and in Siesta Key Village along Ocean Boulevard.


Mote A-scare-rium
5-8 p.m. at Mote Marine Laboratory and Aquarium, 1600 Ken Thompson Parkway, City Island
Free with admission
Visit Mote.org.

Come enjoy family friendly, spooky delights at Mote this Halloween. Trick-or-treat at special stations throughout the aquarium. Activities and entertainment include a scavenger hunt to win a prize, underwater pumpkin carving, the coloring table and photo booth.


Three skeletons made their way through St. Armands Circle with a saxophone during the 2021 Fright Night.
Photo by Nat Kaemmerer

Fright Night in the Circle
6-8:30 p.m. at St. Armands Circle
Free
Visit StArmandsCircleAssoc.com.

Fright Night transforms St. Armands Circle into pure Halloween fun. Storefronts will be adorned with spooky decor, ready to set the stage for the wandering spirits of St. Armands. Look out for frightening characters around every corner as statues filled with Halloween spirit may cause a fright. Adults and children can trick-or-treat throughout the Circle, with numerous retailers and restaurants getting into the Halloween spirit with candy and customized promotions.


Wednesday, Nov. 1

Carl Rimi
7 p.m. at McCurdy’s Comedy Theatre, 1923 Ringling Blvd.
$25
Visit McCurdysComedy.com.

Carl Rimi’s credits include Comedy Central’s “Laugh Riots,” NBC, CBS, ABC Family and more. He also starred in the Independent Christian film, “Bonk.” Runs through Nov. 5. 


The Irish group "Celtic Thunder" plays the Van Wezel Performing Arts Hall on Nov. 1.
Courtesy image

Celtic Thunder Odyssey
7:30 p.m. at Van Wezel Performing Arts Hall, 777 N. Tamiami Trail
$55-$95
Visit VanWezel.org.

The combined voices of Celtic Thunder lead vocalists Ryan Kelly, Damian McGinty, Neil Byrne and Emmet Cahill bring force to this musical journey through traditional and contemporary Irish music, while each singer demonstrates a unique voice and style.

 

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