🌴 What's Happening in Naples October 12 - 18

Hockey is back, the kids have a day off and the stone crab boats go out Thursday. The Everblades raise a banner and hand out 7,000 light-up bracelets at Saturday's home opener, while Boo at the Zoo runs its second weekend and Collier Parks gives away free chocolate cupcakes in Golden Gate Estates. Midweek you get a prize-winning jazz singer at Artis-Naples, an America's Got Talent runner-up at Off The Hook and sunrise Pilates on Vanderbilt Beach. It is laid out one day at a time, so find tonight and go from there.

We recommend confirming with event hosts for complete details and current schedules

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🗓️ Monday, October 12

🎃 Boo at the Zoo
📅 Date: Monday, October 12, 2026
📍 Location: Naples Zoo at Caribbean Gardens, 1590 Goodlette-Frank Rd, Naples, FL 34102
🦁 Details: The holiday Monday closes out the first Boo weekend, with costumed characters, trick-or-treating for kids 12 and under, the Pirate Expedition Cruise and a dinosaur encounter, all included with admission. Costumes are welcome, but leave balloons and face-covering adult masks at home. Check the zoo's page for hours.

🌿 Kids Free Day at Naples Botanical Garden
📅 Date: Monday, October 12, 2026
⏰ Time: 9:00 AM to 5:00 PM
📍 Location: Naples Botanical Garden, 4820 Bayshore Dr, Naples, FL 34112
🌺 Details: Ages 4 to 17 get in free all day, which saves you $12 a head, and kids programming runs from 10 to noon. Adults still pay $27. It is the cheapest way to tire everybody out on a school-holiday Monday.

🎤 Sheena Reagan at Off The Hook
📅 Date: Monday, October 12, 2026
⏰ Time: 7:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
🏡 Details: Billed as "Florida's Funniest Female," she has opened for Jon Lovitz and Caroline Rhea and also happens to sell real estate, so expect some open-house material. There is a two-item minimum.

🎺 Stardust Memories Big Band Concert
📅 Date: Monday, October 12, 2026
⏰ Time: 7:00 PM to 9:00 PM
📍 Location: Cambier Park Bandshell, 755 8th Ave S, Naples, FL 34102
🎷 Details: A full big band plays swing-era standards under the stars, a block off Fifth Avenue South. Bring a lawn chair, and have dinner on Fifth first.

🎸 Open Mic Night with Bryan & Steve
📅 Date: Monday, October 12, 2026
⏰ Time: 7:00 PM to 10:00 PM
📍 Location: The Oasis, 1046 Pine Ridge Rd, Naples, FL 34105
🍔 Details: Bring a guitar or just bring an appetite, because the $11 smash burger special runs all night. Some of the regulars are genuinely good.

🗓️ Tuesday, October 13

🎃 Pumpkins and Pilates
📅 Date: Tuesday, October 13, 2026
⏰ Time: 7:00 AM to 8:30 AM
📍 Location: Vanderbilt Public Beach, 100 Vanderbilt Beach Rd, Naples, FL 34108
🧘 Details: Jaclyn Ortiz leads sunrise Pilates on the sand, followed by pumpkin painting, giveaways and local vendors. Beginners are welcome, and you will have done core work and a craft project before most people have had coffee.

🐐 Tuesday Night Tuck-In on the Farm
📅 Date: Tuesday, October 13, 2026
⏰ Time: 3:30 PM to 5:30 PM
📍 Location: Empowerment Farm, 2600 Garland Rd, Naples, FL 34117
🐑 Details: Open play, then the kids help with evening chores and put the animals to bed before story time in the Pavilion. It is $25 per family of up to two adults and three kids, and your children may finally see bedtime from your side.

🥃 Whiskey Tasting with Angel's Envy
📅 Date: Tuesday, October 13, 2026
⏰ Time: 6:30 PM to 8:00 PM
📍 Location: Oak & Stone, 2270 Logan Blvd N, Naples, FL 34119
🍽️ Details: For $59 you get a welcome cocktail, five whiskey and bourbon pours with food pairings and a bourbon expert talking you through each one. You also get 15% off dinner afterward, and it is 21 and up.

😂 Brandon Trusso at Off The Hook
📅 Date: Tuesday, October 13, 2026
⏰ Time: 7:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
📱 Details: A Buffalo-born, New York-based comic with over a million followers and a lot to say about dating and family. Doors open at 5.

🧠 Trivia Night at The Oasis
📅 Date: Tuesday, October 13, 2026
⏰ Time: 7:30 PM
📍 Location: The Oasis, 1046 Pine Ridge Rd, Naples, FL 34105
🏆 Details: Spotlight Trivia runs the weekly game. Bring the friend who knows sports and the friend who knows 90s sitcoms, and you are halfway there.
⏰ Time: 6:00 PM
📍 Location: 2132 Tamiami Trail North, Naples, FL
📖 Details: Friday open mic at the organic cafe. Singer-songwriter heavy, family-friendly, espresso carrying you into the second half.

🎲 Twisted Bingo: Music Bingo Naples
📅 Date: Monday, June 15, 2026
⏰ Time: 7:00 PM
📍 Location: Dylan's Drafthouse, Naples
🍻 Details: Music bingo to kick the week off. Free to play, name-that-tune chaos, drink specials all night.

🍺 Monday Trivia on Marco Island
📅 Date: Monday, June 15, 2026
⏰ Time: 7:00 PM
📍 Location: Paddy Murphy's Irish Pub, Marco Island
🧠 Details: Classic pub trivia in an Irish bar on Marco. Bring a smart friend, split the pitcher, argue about the answers.

🎯 Monday Night Trivia in Estero
📅 Date: Monday, June 15, 2026
⏰ Time: 7:00 PM
📍 Location: Naples Flatbread Kitchen & Bar, Estero
🍕 Details: Trivia over wood-fired flatbread just up the road. The second trivia option of the night if Marco is too far a drive.

🏁 DeVoe Cadillac F1 Watch Party
📅 Date: Sunday, June 14, 2026
⏰ Time: Happening now
📍 Location: Celebration Park, Naples
🏎️ Details: Race-day watch party at the food-truck park. Big screens, cold drinks, and a real crowd of motorsport people. 18 already marked interested.

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🗓️ Wednesday, October 14

🎷 Lucy Wijnands: All That Jazz
📅 Date: Wednesday, October 14, 2026
⏰ Time: 6:00 PM and 8:30 PM
📍 Location: Daniels Pavilion, Artis-Naples, 5833 Pelican Bay Blvd, Naples, FL 34108
🎶 Details: The 2021 Ella Fitzgerald Vocal Competition winner sings with the Naples Philharmonic Jazz Orchestra, after stints alongside Ron Carter and the Birdland Big Band. Two shows, so early birds and night owls both get a turn, and the box office is 239-597-1900.

🎤 Chris Turner at Off The Hook
📅 Date: Wednesday, October 14, 2026
⏰ Time: 7:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
🎙️ Details: The America's Got Talent Season 20 runner-up freestyles a brand-new hour with the audience every night. Sit up front only if you are ready to get rhymed about.

🐶 Wooftop Wednesday at Rooftop at Riverside
📅 Date: Wednesday, October 14, 2026
⏰ Time: 5:00 PM to 8:00 PM
📍 Location: Rooftop at Riverside, 27333 Old 41 Rd, Bonita Springs, FL 34135
🍹 Details: Rooftop happy hour with drink specials, and your dog is on the guest list. Accept now that the dog will be the most popular member of your group.

🎱 Twisted Bingo at Rooftop at Riverside
📅 Date: Wednesday, October 14, 2026
⏰ Time: 7:00 PM to 9:00 PM
📍 Location: Rooftop at Riverside, 27333 Old 41 Rd, Bonita Springs, FL 34135
🎉 Details: Fast rounds, music bingo, prizes and a jackpot that grows every week. If you came for Wooftop, just stay in your seat.

🗓️ Thursday, October 15

🚶 Downtown Bonita Springs Walking History Tour
📅 Date: Thursday, October 15, 2026
⏰ Time: 10:00 AM to 11:00 AM
📍 Location: Historic McSwain Home Museum and Gardens, 27451 Old 41 Rd, Bonita Springs, FL 34135
🏛️ Details: A marine biologist and naturalist walks you through the Imperial River's role in early Bonita, how the town got its name and the characters behind its lore. It is a morning hour, so the history comes before the heat.

🎵 Motown with Ross Brown at Rooftop at Riverside
📅 Date: Thursday, October 15, 2026
⏰ Time: 5:00 PM to 7:00 PM
📍 Location: Rooftop at Riverside, 27333 Old 41 Rd, Bonita Springs, FL 34135
🕺 Details: Golden-era Motown on a rooftop at sunset. Singing along to the Temptations is encouraged, and dancing is optional.

🍷 South of France Wine Tasting
📅 Date: Thursday, October 15, 2026
⏰ Time: 5:30 PM to 7:00 PM
📍 Location: Vichino's Cafe & Wine Bar, 25987 S Tamiami Trail, Bonita Springs, FL 34134
🧀 Details: Five wines from Languedoc and Bordeaux, a pretzel charcuterie and a guest who works directly with the vineyards. Tickets are advance only and the listing says they are going fast.

😂 Brittany Brave at Off The Hook
📅 Date: Thursday, October 15, 2026
⏰ Time: 7:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
🌶️ Details: Miami New Times named her Best Comedian of 2021, and her hour Muchacha is billed as "frantic, raunchy and raw." Maybe leave Grandma home for this one.

🗓️ Friday, October 16

🖼️ The Surrealist International: Fifty Years of Dreams Lecture
📅 Date: Friday, October 16, 2026
⏰ Time: 4:00 PM
📍 Location: Ubben Signature Event Space, Artis-Naples, 5833 Pelican Bay Blvd, Naples, FL 34108
🎨 Details: Matthew Gale, the former head of displays at Tate Modern, walks through The Baker Museum's new surrealism show, drawn entirely from Tate's collection. Your ticket gets you into the museum the same day, so you can go see the strange stuff in person.

🛍️ Flamingo Island Flea Market
📅 Date: Friday, October 16 through Sunday, October 18, 2026
⏰ Time: 8:00 AM to 4:00 PM
📍 Location: Flamingo Island Flea Market, 11902 Bonita Beach Rd SE, Bonita Springs, FL 34135
🧺 Details: Hundreds of vendors indoors and out, with antiques, collectibles, crafts, food and live entertainment. Sunday tends to bring the best deals, since nobody wants to pack it all back up.

🎤 Arynne Wexler at Off The Hook
📅 Date: Friday, October 16 and Saturday, October 17, 2026
⏰ Time: Friday 6:30 PM and 8:30 PM, Saturday 6:00 PM and 8:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
📈 Details: A Wharton grad and former Goldman Sachs trader who quit to go viral picking the arguments everybody else avoids at dinner. There is a two-item minimum, and leaving finance clearly did wonders for her material.

🏴‍☠️ Live Music Fridays at Compass Margaritaville
📅 Date: Friday, October 16, 2026
⏰ Time: 6:00 PM to 9:00 PM
📍 Location: Compass Hotel by Margaritaville, 4805 Tamiami Trail N, Naples, FL 34103
🎸 Details: Low-key live music at the hotel bar on 41, with no planning required. It is the easiest way to start a weekend.

👻 Galaxy's Fright Nights
📅 Date: Friday, October 16 and Saturday, October 17, 2026
📍 Location: Collier County Fairgrounds, 751 39th Ave NE, Naples, FL 34120
🤡 Details: An indoor haunt every Friday and Saturday in October, so it runs rain or shine, and parking is free. Hours and 2026 prices still are not posted, so check the site before you drive out.

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🗓️ Saturday, October 17

🧺 Third Street South Farmers Market
📅 Date: Saturday, October 17, 2026
⏰ Time: 7:30 AM to 11:30 AM
📍 Location: Lot at Gordon Dr and 13th Ave S, behind Tommy Bahama, Naples, FL 34102
🍅 Details: Still in its summer lot until it moves back onto Third Street in November. The good tomatoes go early.

🥕 Vanderbilt Farmers Market
📅 Date: Saturday, October 17, 2026
⏰ Time: 8:00 AM to 1:00 PM
📍 Location: Galleria Shoppes at Vanderbilt, 2355 Vanderbilt Beach Rd, Naples, FL 34109
🍯 Details: Produce, local honey, specialty foods and crafts, with the vendor list growing every week as the snowbirds arrive. Bring bags and some self-control near the baked goods.

🏎️ Exotics & Espresso at Ferrari of Naples
📅 Date: Saturday, October 17, 2026
⏰ Time: 9:00 AM to 11:00 AM
📍 Location: Ferrari of Naples, 11291 Tamiami Trail N, Naples, FL 34110
☕ Details: A monthly car meet open to every make and model, with free coffee and breakfast bites from Narrative Coffee Roasters. Sip a free latte and pretend you are just browsing, and RSVP on the event page.

🎃 Boo at the Zoo, Weekend Two
📅 Date: Saturday, October 17 through Monday, October 19, 2026
📍 Location: Naples Zoo at Caribbean Gardens, 1590 Goodlette-Frank Rd, Naples, FL 34102
🦒 Details: Round two of trick-or-treating past the giraffes, with princesses, superheroes and the dinosaur encounter, included with admission. Let the kids wear the costume early, because they will anyway.

🧁 National Chocolate Cupcake Day
📅 Date: Saturday, October 17, 2026
⏰ Time: 12:00 PM to 2:00 PM
📍 Location: Big Corkscrew Island Regional Park, 810 39th Ave NE, Naples, FL 34120
🍫 Details: Collier Parks is giving away free chocolate cupcakes while supplies last. That is the whole event, and it does not need anything else.

🏒 Florida Everblades Opening Night and Banner Raising
📅 Date: Saturday, October 17, 2026
⏰ Time: 7:00 PM
📍 Location: Hertz Arena, 11000 Everblades Pkwy, Estero, FL 33928
🏆 Details: The home opener against the Orlando Solar Bears, with a banner raising, LED bracelets for the first 7,000 fans and a Publix tailgate from 5 to 7. Wear green and get ready to yell at a referee you have never met.

🔥 Splou Live at Off The Hook
📅 Date: Saturday, October 17, 2026
⏰ Time: 10:15 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
🇩🇴 Details: The Bronx-born Dominican-American comic brings his viral Spanglish sketches and family stories to a late show. VIP puts you in the first few rows, and your abuela would mostly approve.

🗓️ Sunday, October 18

🎻 Beethoven and Fanny Mendelssohn: Sypert Salon
📅 Date: Sunday, October 18, 2026
⏰ Time: 3:00 PM
📍 Location: Daniels Pavilion, Artis-Naples, 5833 Pelican Bay Blvd, Naples, FL 34108
🎶 Details: Naples Philharmonic players perform Fanny Mendelssohn-Hensel's String Quartet in E-flat and Beethoven's Piano Trio in G Major in an intimate salon setting. It is a very civilized way to spend a Sunday afternoon.

🌴 Live Entertainment Sundays at Compass Margaritaville
📅 Date: Sunday, October 18, 2026
⏰ Time: 2:00 PM to 5:00 PM
📍 Location: Compass Hotel by Margaritaville, 4805 Tamiami Trail N, Naples, FL 34103
🍹 Details: An easy afternoon set that fits neatly between brunch and admitting the weekend is over. Just show up.

🌎 Luz Pazos at Off The Hook
📅 Date: Sunday, October 18, 2026
⏰ Time: 6:00 PM
📍 Location: Off The Hook Comedy Club, 2500 Vanderbilt Beach Rd, Suite 1100, Naples, FL 34109
🎤 Details: Born in Peru and educated in Italy, the LA comic has credits on Kroll Show and Comedy Chingonas and has opened for Gabriel Iglesias. Doors open at 4, so you can grab a good seat and a snack.

🎭 All Week

🍝 Over the River and Through the Woods
📅 Date: Wednesday, October 7 through Sunday, October 25, 2026
⏰ Time: 7:30 PM Wednesday to Saturday, 2:00 PM Sunday
📍 Location: The Naples Players, Kizzie Theater at the Sugden Community Theatre, 701 5th Ave S, Naples, FL 34102
👵 Details: Nick has Sunday dinner with his four Italian grandparents every week, right up until he announces he is moving away. Tickets run $25 to $67, and you will probably call your grandmother afterward.

🖋️ Rembrandt: Masterpieces in Black & White
📅 Date: Through Sunday, January 24, 2027
📍 Location: Naples Art Institute, 585 Park St, Naples, FL 34102
🖼️ Details: Etchings on loan from the Rembrandt House Museum in Amsterdam, plus work by his pupils, on the last stop of the U.S. tour. It is the closest you will get without a flight to Amsterdam.

🌴 Historias del aire y del suelo | Stories of Air and Soil
📅 Date: Daily, through Sunday, October 25, 2026
⏰ Time: 8:00 AM to 2:00 PM
📍 Location: Kapnick Hall, Naples Botanical Garden, 4820 Bayshore Dr, Naples, FL 34112
🎨 Details: Puerto Rican artist Pseudomero's two-part show on palms and bromeliads connects the Everglades to the island. It is included with admission and closes October 25, so this is the final stretch.

⚠️ Please verify event details and availability with the respective venues or organizers, as schedules may change.

📰 What's Happening in Naples

🔗 Naples Set a February Special Election to Fill Penniman's Seat
City Council picked February 2, 2027, for the vote, with candidate qualifying from December 4 through December 14 and the winner serving out the rest of Linda Penniman's term through 2028.

🔗 Record Rain Flooded Old Naples and 22 Cars Got Towed
A record 4.8 inches fell Wednesday and swamped streets like Fourth and Sixth Avenues South, police logged 26 flooded-vehicle reports and officers used a swamp buggy for rescues for the first time.

🔗 Naples Police Got a Budget Boost for Drones, Body Cameras and a Cyber-Crime Unit
Council raised camera and drone spending from $120,000 to $650,000 and added officers, in-car cameras, evidence storage, VR training and a brand-new unit dedicated to cyber crime.

🔗 Naples Took a First Step Toward Hosting the 2028 Olympic Torch Relay
Council told City Manager Gary Young to buy an event insurance policy of up to $5,000 so the city can become an LA28 Cauldron City and host a three to four mile relay leg in spring 2028.

🔗 Commerce Bank Paid $24.1 Million for the FineMark Building in Pelican Bay
The six-story, 41,712-square-foot building at 800 Laurel Oak Drive beside Waterside Shops sold for about $560 a square foot, which is likely a record for Naples office space.

🔗 Paragon Theaters Wants to Reopen the Old Alamo Drafthouse at Mercato
Paragon plans to lease the 11-screen theater that closed September 9, possibly reopening by December or January, while cutting its Pavilion location on Vanderbilt Beach Road from 10 screens to six.

🔗 Crayton Road Closed After a Sinkhole Opened Near Parkview Drive
Police shut Crayton Road between Parkview and Binnacle Drives near 3505 Crayton Road, with detours posted and Mermaids Bight traffic routed northbound until repairs are done.

🔗 The NTSB Blamed Fuel Mismanagement for April's Marco Island Plane Crash
Investigators found the pilot kept straying from his planned altitude and route until one tank ran dry, forcing a road landing outside Marco Island Executive Airport that he walked away from unhurt.

🔗 A Naples Landscaper Is Accused of Threatening a Family Over $100,000
Police arrested Christopher Cueva, who they say sent death threats by text, voicemail and social media to a family, including two members over 65, that withheld payment after he abandoned their post-Ian yard job.

🔗 A Homeowner Was Charged After 100 Teens Fled a House Party
Deputies charged 45-year-old Bruce Young under Florida's open house party law after more than 100 juveniles ran from a sophomore party at his Shady Oaks Lane home, where they found open alcohol and the smell of marijuana.

🔗 An Ave Maria Couple Is Out $84,000 After Their Contractor Filed for Bankruptcy
The Birklee Contracting owner walked off a $67,000 kitchen job, told the state his firm had no debts and then listed $1.3 million in business debts in bankruptcy court the very next day.

🔗 Immokalee's New Pediatric Health Center Officially Opened
The Naples Children Foundation cut the ribbon on its 3,600-square-foot center at 429 N. First St., which offers dental, vision, therapy and behavioral care and has already served nearly 6,000 kids.

🔗 Youth Haven Landed $153,000 to Grow Its Behavioral Health Staff
The two-year Naples Children Foundation grant pays for a registered intern and supervisor at Collier's only emergency shelter for abused and homeless youth ages 6 to 21, part of a $2 million push funding 17 interns.

🔗 A Panther Killed on State Road 29 Was Collier's Seventh This Year
The 6-year-old male was found south of Immokalee, likely hit by a vehicle, bringing Florida to 12 panther deaths in 2026, with seven of them in Collier County.

🔗 Naples Zoo Hatched Its First Southern Crested Screamer Chicks
Parents Jamie Lee and Peggy are raising three chicks hatched in August under a national breeding plan, and the family is due out on public habitat later this month, so look for them at Boo at the Zoo.

🔗 Marco Patriots Came Home Early After Isaias Fell Apart
The Marco Island search and rescue volunteers deployed to Bay County, but the storm's east side broke up before landfall and they were back within 24 hours while FPL worked through more than 378,000 outages.