What's Happening in Naples This Week: September 10–16, 2026

This week carries more weight than most. September 11 marks 25 years since the attacks that changed the country, and Collier County has a free, public candlelight ceremony to mark it. Beyond the remembrance, the week offers a strong entertainment lineup: a returning comedian, a Fifth Avenue outdoor evening, a free movie under the stars, and one last week to catch the Naples Art Institute's American Modernism exhibition before it closes Saturday. Sizzle Dining continues all month.

😂 Shayne Smith — 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

Shayne Smith returns to Off the Hook for another Naples run — the tattooed, sharp-witted comedian who built his following through social media and touring is back for a multi-night engagement. His disarming self-awareness and precision timing landed him one of the strongest audience responses of the summer when he played Naples in August. Thursday is the quietest night of his run — easier parking, better energy. A strong way to open the week.

🎨 New Ways of Seeing: American Modernism — Final Days📍 Naples Art Institute, 585 Park Street, Naples

🕙 Open through Saturday September 13 | 🎟 $15 | Members free | naplesart.org | 239-659-3338

This is the last week to catch the Naples Art Institute's summer exhibition exploring American art's evolution from 1915 to 1965 through paintings, drawings, and prints from a private collection. The exhibition closes Saturday — if you've been meaning to go, this week is the window. $15 admission, free for members.

🕯️ 25th Anniversary Candlelight Ceremony — Collier County Freedom Memorial📍 Fred W. Coyle Freedom Memorial, Vineyards Community Park, 6231 Arbor Blvd W, Naples

🕗 Evening | 🎟 Free and open to the public

Gather at the Collier County Freedom Memorial for a special candlelight ceremony marking 25 years since the September 11, 2001, attacks on the World Trade Center and Pentagon and the crash of Flight 93 in Shanksville, Pennsylvania. The remembrance is free and open to the public. A solemn, community event worth attending — particularly this year, on the quarter-century mark. SWFL Family

🌆 Evening on Fifth📍 5th Avenue South, downtown Naples

🕡 6:30 PM – 9:30 PM | 🎟 Free | fifthavenuesouth.com

Evening on Fifth runs Friday September 11 from 6:30 to 9:30 PM on Fifth Avenue South — an outdoor community gathering with live music, street performers, dining specials, and the natural energy of one of Naples' most beautiful outdoor corridors on a September evening. Free admission. Walk, shop, dine, and enjoy the avenue at its most alive.

🛍️ 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 in the heart of downtown. Start here.

😂 Shayne Smith — Two Shows — Final Night📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕕 Two showtimes | 🎟 offthehookcomedy.com

Final night of Shayne Smith's Naples run. Two shows Saturday — book in advance.

🎨 New Ways of Seeing — FINAL DAY📍 Naples Art Institute, 585 Park Street, Naples

🎟 $15 | Members free | naplesart.org

The American Modernism exhibition closes today permanently. Last chance.

🎶 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.

🎭 Broadway Babies — Children's Theater📍 Gulfshore Playhouse, 100 Goodlette-Frank Road South, Naples

🕙 10:00 AM | 🎟 $40 | gulfshoreplayhouse.org | 239-261-7529

Gulfshore Playhouse's Saturday children's theater class for ages 2–4 continues — a 45-minute program exploring Broadway through music, dance, and creative movement with caregivers. Runs through September 26. A charming Saturday morning option for families with toddlers.

🍽️ Sizzle Dining — Weekend Brunch Window
📍 140+ participating restaurants | sizzledining.org

Sunday brunch is one of the most underutilized Sizzle Dining windows. Crowds are lighter than Friday and Saturday evenings and many restaurants offer their strongest Sizzle menus at brunch. Remember to ask your server whether portions are the same size as the regular menu before ordering.

🎷 Jebry & Friends Jazz Jam📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕕 6:00 PM – 9:00 PM | 🎟 Free | dogtoothnaples.com

Every Monday without exception — the most consistent free live jazz experience in Naples. No cover, no reservation.

🎬 Movies on the Lawn — "Lilo & Stitch" (2025)📍 Mercato, 9127 Strada Place, Naples

🕖 7:30 PM (at dusk) | 🎟 Free

The third Tuesday of every month, Mercato hosts a free outdoor movie on the lawn. This month's feature is the 2025 live-action Lilo & Stitch. Lawn chairs, blankets, and snacks are welcome. Admission is completely free. A genuinely great family Tuesday evening that costs nothing.

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

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

Spotlight Trivia runs every Tuesday at 7:30 PM at The Oasis. A casual, fun option for teams of two to six. No cover, full menu and bar available.

🎨 Art After Hours — Baker Museum at Artis-Naples📍 The Baker Museum, Artis-Naples, 5833 Pelican Bay Blvd, Naples

🕕 6:00 PM – 9:00 PM | 🎟 Free admission | artisnaples.org

The last Wednesday of every month, Artis-Naples opens The Baker Museum completely free from 6 to 9 PM — with live music by local musicians and Heidi's Place concessions running alongside the open galleries. Three hours of free museum access and live music in one of the best art spaces in Southwest Florida.

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

🕖 7:00 PM | 🎟 From $33 | offthehookcomedy.com

Brad Upton opens his Naples run Wednesday evening — known for his relatable, observational humor about getting older and the absurdities of everyday life, Upton has built one of the most loyal audiences in regional comedy. A strong midweek option.

🍽️ Sizzle Dining 2026
All September | 140+ restaurants | sizzledining.org | Book directly with restaurants

📸 Untold Stories: Mexican Railroad Braceros of WW2
Through December 23 | Naples Depot Museum, 1051 5th Ave S | colliermuseums.com | Free

🌿 Historias del aire y del suelo — Naples Botanical Garden
Through October 25 | Included with garden admission | naplesgarden.org

🎨 Through the Light of the Mangroves — Rookery Bay
Through October 29 | Rookery Bay Learning Center, 300 Tower Road | Free with reserve admission

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Email us at [email protected] with your event name, date, time, location, and a short description.