What's Happening in Naples This Week: September 17–23, 2026

September is winding down — but it's finishing strong. Brad Upton brings his relatable observational comedy to Off the Hook for four straight nights. The Vanderbilt Beach Farmers Market opens its fall Saturday season. Free Zoo Day is Saturday. Books on Third hosts its popular evening series. And the final stretch of Sizzle Dining is here — if you haven't made a reservation yet, this week is your window before the month closes.

September 1–30 | 140+ restaurants across Lee and Collier counties
🌐 sizzledining.org

The last full week of Sizzle Dining. 140 participating restaurants offering 2 and 3-course prix-fixe menus. Browse sizzledining.org, read the actual menu before you book, and remember to ask your server whether the Sizzle portions match the regular menu before you order. Every meal donates $1 to Blessings in a Backpack.

Flavors of Fifth also closes September 30 at fifthavenuesouth.com — 14 Fifth Avenue South restaurants participating through the end of the month.

😂 Brad Upton — Off the Hook Comedy Club📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕖 7:00 PM | 🎟 Tickets at offthehookcomedy.com | 239-389-6901

Brad Upton opens a four-night Naples run Thursday evening. Known for sharp, relatable observational humor about aging, family, and the absurdities of everyday life, Upton has built one of the most loyal regional comedy followings in the Southeast over more than two decades on the circuit. His material is the kind that has audiences nodding and laughing at the same time — because they've been there. Thursday is the quietest night of the run and often the most relaxed experience. A strong opener for the week.

📚 Books on Third — Evening Author Series📍 Books on Third, 1300 3rd Street South, Naples

🕕 6:00 PM – 8:30 PM | 🎟 Free | booksonthird.com

Books on Third continues its fall author evening series on the balcony above Third Street South. A free, intimate literary gathering in one of Old Naples' most charming settings — bring a friend, browse the shelves, and spend an evening in the kind of neighborhood bookstore that most cities have lost. Check booksonthird.com for the specific author and book featured this week.

😂 Brad Upton — Off the Hook📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕗 8:30 PM | 🎟 offthehookcomedy.com

Friday night show at 8:30 PM. Book in advance — Friday nights at Off the Hook sell consistently through the season.

🛍️ Third Street South Farmers Market📍 Third Street South, downtown Naples

🕖 7:30 AM – 11:30 AM | 🎟 Free

The 30-year Saturday morning institution in Old Naples. Fresh produce, baked goods, local vendors, and strong coffee. Start every Naples Saturday here.

🥕 Vanderbilt Beach Farmers Market — Fall Season Opens📍 Vanderbilt Beach area, North Naples

🕗 8:00 AM – 1:00 PM | 🎟 Free

The Vanderbilt Beach Farmers Market opens its fall Saturday season this week — running from 8 AM to 1 PM, an extended schedule compared to the summer hours. A strong North Naples alternative to the Third Street market, with fresh produce, local vendors, and a more neighborhood feel. If you haven't visited the Vanderbilt market in a while, the fall opening weekend is the time to go.

🦁 Free Zoo Day — Collier County Residents📍 Naples Zoo at Caribbean Gardens, 1590 Goodlette-Frank Road, Naples

🕘 9:00 AM — entry until 3:30 PM | 🎟 Free with Collier County photo ID | napleszoo.org

The first Saturday of every month, Collier County residents get free all-day admission to the Naples Zoo. Bring a matching photo ID with your Collier County address. Entry closes at 3:30 PM — plan accordingly. Big cats, primates, giraffes, and the beloved boat tour through islands of free-ranging primates. The best free family event of the week.

🌿 Audubon Corkscrew Swamp Sanctuary — Free Admission Day📍 Corkscrew Swamp Sanctuary, 375 Sanctuary Road West, Naples

🕘 All day — Saturday September 19, 2026 | 🎟 Free admission | Get tickets: audubon.org/corkscrew/events

Audubon's Corkscrew Swamp Sanctuary is hosting a special free community day featuring a bird talk by Helen Midney, Museum Manager for the Immokalee Pioneer Museum at Roberts Ranch, a community bingo game, a collaborative weaving activity, and an alligator information table right on the boardwalk. Mexican ice cream bars will be available for purchase at the Blair Visitor Center throughout the day.

Between activities, visitors are encouraged to walk the boardwalk through one of the most magnificent old-growth bald cypress forests remaining in North America — a landscape that looks exactly as it did thousands of years ago. Free admission days at Corkscrew are rare. This one comes with programming. Don't miss it

🎶 Sounds on Strada — Live Music at Mercato📍 Mercato Piazza, 9110 Strada Place, North Naples

🕕 6:00 PM – 8:00 PM | 🎟 Free

Mercato's weekly Saturday live music series in the Piazza. Lawn chairs welcome, no outside coolers. The penultimate Sounds on Strada of the summer season — the outdoor series wraps up as season approaches.

😂 Brad Upton — Final Show📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕕 6:00 PM | 🎟 offthehookcomedy.com

Final performance of Brad Upton's Naples run. Sunday at 6 PM — the last chance to catch this engagement.

🌿 Sunday Morning at the Botanical Garden📍 Naples Botanical Garden, 4820 Bayshore Drive, Naples

🕘 8:00 AM – 5:00 PM | 🎟 Adults $27, Children 4–17 free | naplesgarden.org

September is one of the most beautiful months to visit the Naples Botanical Garden — the summer bloom is at its peak and the garden is far less crowded than it will be once season begins in November. Sunday morning is the best time to go — cooler temperatures, lighter crowds, and the garden at its most peaceful. The Historias del aire y del suelo exhibition by Puerto Rican artist Pseudomero continues through October 25, included with admission.

⚖️ Collier County Commission — East Naples Golf Course Vote📍 Collier County Government Center, 3299 Tamiami Trail East, Naples

🕙 9:00 AM | 🎟 Free — public meeting | colliercountyfl.gov

The Collier County Board of Commissioners votes Tuesday morning on the proposed Hyper Club — a private luxury motorsports community and golf club proposed for 531 acres near Alligator Alley on the western edge of the Everglades. The Planning Commission approved it 5-1 in August. Environmental groups including the South Florida Wildlands Association and Audubon Western Everglades are opposed, citing impacts to Florida panther habitat, 142 acres of wetlands, and the adjacent Florida Panther National Wildlife Refuge.

NNN has been covering this story since July. This vote determines whether the project moves forward or is rejected at the county level. If you care about what happens on the eastern edge of Collier County's conservation land — Tuesday morning is the moment to pay attention.

🎯 Spotlight Trivia Night — The Oasis Naples📍 The Oasis, 1046 Pine Ridge Road, Naples

🕖 7:30 PM | 🎟 Free to play | theorasisnaples.com

Spotlight Trivia every Tuesday at 7:30 PM at The Oasis. Teams of two to six, no cover, full menu and bar available.

🎤 Andy Gross — Off the Hook Comedy Club📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕖 7:00 PM | 🎟 From $35 | offthehookcomedy.com

Andy Gross — ventriloquist, magician, comedian, and one of the most uniquely talented performers in entertainment — opens a midweek show at Off the Hook Wednesday evening. Known for his jaw-dropping ventriloquism combined with stand-up comedy and illusion, Gross has appeared on America's Got Talent, The Tonight Show, and countless other national platforms. A genuinely different kind of comedy night — family-friendly but just as entertaining for adults. Worth experiencing at least once.