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- 🎯 Things to Do Oct. 9 – Oct. 15, 2025 (Naples / SWFL Edition)
🎯 Things to Do Oct. 9 – Oct. 15, 2025 (Naples / SWFL Edition)
Robert Desiano
October 08, 2025
As autumn settles in across Southwest Florida, the calendar is lighting up — with music, running, art, family fun, and more. Here are standout events and ideas for your week ahead (Oct. 9–15).
🔍 Featured Events to Check Out
Date | Event | Where | Time | Details |
|---|---|---|---|---|
Thu, Oct 9 | Charlie Berens: Working It All Out (Comedy Show) | Naples | 6:30 PM | A one-night performance from this popular comedian. |
Thu, Oct 9 | Evening on Fifth (Live Performances) | 5th Avenue South, Naples | 6:30 PM | Music and sidewalk performances, part of the monthly series. |
Fri, Oct 10 | Rocktoberfest Half Marathon & 5K | North Collier Regional Park | 6:30 AM start | Run plus festival atmosphere. |
Sun, Oct 12 | Rock the Block (Mercato event) | Mercato, Naples | 6:30 PM | Neighborhood block party with live music. |
Wed, Oct 15 | “Bobby Broom: All That Jazz” | Naples | 6:00 PM | Jazz concert with Naples Philharmonic Jazz Orchestra. |
🌼 Ongoing / Seasonal Highlights & Ideas
Artists in Bloom at Naples Botanical Garden — Exhibition in Kapnick Hall, open through mid-October.
Naples Theater October Shows — Check weekly schedule for plays and performances.
Visit Naples Events Calendar — Keeps updated listings for art walks, pop-ups, and community happenings.
Paradise Coast Events Directory — For Marco, Everglades, & Bonita event listings.
🌴 Ideas for Almost-Any Day
Sunrise walk at Naples Pier / beaches — peaceful, picturesque, and free.
Bike or kayak local preserves — e.g. Delnor Wiggins Pass, Collier-Seminole, or Clam Pass.
Stroll galleries & street fairs — Third Street South, 3rd Street S., art walks.
Sunset at Vanderbilt or Lowdermilk Park — perfect photo ops.
Visit Naples Zoo or Botanical Garden — especially on quieter weekdays.