What’s On in Naples | Oct. 15 – Oct. 22, 2025

Fall is in full swing on the Paradise Coast, and Naples is buzzing with a lineup of cultural, community, and seasonal events. Here are top picks to plug into your calendar this week.

🎼 Music, Theater & Performances

• Bobby Broom / All That Jazz
  Kick off the week with a soulful jazz performance as the Naples Philharmonic Jazz Orchestra presents the All That Jazz series, featuring guitarist Bobby Broom.

• Ehnes Plays Mozart — Chamber Music
  On Oct. 19 & 21, enjoy intimate chamber concerts featuring violinist James Ehnes in collaboration with the Naples Philharmonic.

• Classics in Hollywood
  Wrap the week with a narrative music experience on Oct. 22 that blends film scores and storytelling. “Ada and the Engine” — The Naples Players
  Running Oct. 15 through Nov. 9 in the Price Studio Theater, this theatrical production brings inventive storytelling to center stage.

🎨 Art, Markets & Creative Vibes

• Artists in Bloom (Naples Botanical Garden)
  Ongoing throughout the week, this exhibit features works inspired by the local landscape and natural beauty.

• Third Street South Farmers Market
  A reliably fresh and local weekend staple — stroll, shop, and soak in historic Naples’ charm.

• Naples Paint Party – Harvest Moon
  On Saturday, Oct. 18 (4:00 p.m. – 7:00 p.m.), join a Halloween-themed paint & sip at Bad Ass Coffee. Supplies and guidance provided — creativity encouraged.

🚗 Community & Fun Gathering Events

• Wednesday Night Cruise-In
  Car fans unite: Oct. 15 from 7:00 p.m.–11:00 p.m. at Shea’s / Lansdowne parking area — food, drinks, bikes, cars, and community vibe.

• Naples Rocktoberfest Half Marathon & 5K
  Lace up for this fall favorite at North Collier Regional Park. Expect music, community energy, and scenic routes.

• Cars & Coffee 239 — Halloween Edition
  Sunday, Oct. 19 — a Sunday morning cruise among exotic, classic, and themed cars at Mercato. Coffee, tunes, and casual spectacle.

🏛️ Civic, Networking & Local Connects

• October 2025 Luncheon — East Naples Civic & Commerce
  Join local business leaders Oct. 16 (11:30 a.m. – 1:00 p.m.) at The Players Club & Spa. Good for networking and local insight.

📌 Heads-Up & Local Tips

• Check Venues & Tickets: Some events require advance booking, especially concerts and theater.

• Timing & Traffic: Evenings popular; arrive early where parking or access is limited.

• Dress & Comfort: Fall weather is pleasant — dress for evenings but bring a light layer.

• Family-Friendly Options: The botanical garden and farmer’s markets are solid choices for all ages.

• Stay Flexible: Rain or changes might shift outdoor events — always check the event’s page.