October to November Fall Festivities in Naples, Florida

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Autumn in Naples, Florida, offers vibrant events, cultural experiences, and family fun. Here's your complete guide to what's happening this October and November:

🎃 October Events

Haunted Hoedown & Movie on the Lawn
📅 October 21, 2025
📍 Mercato (9132 Strada Pl.)
Trick-or-treating from 5:30 PM followed by a Halloween-themed movie at 7:00 PM.

5th Avenue South Annual Spooktacular
📅 October 25, 2025
📍 Fifth Avenue South
Halloween party, trunk-or-treating, and costume contests for all ages—including pets!

Naples Rocktoberfest Half Marathon & 5K
📅 October 2025 (Check exact date)
📍 North Collier Regional Park, Naples
A festive-themed race followed by celebrations.

Stone Crab Festival
📅 Late October (annual)
📍 Tin City / Naples Waterfront
Celebrate the stone crab season with seafood, music, and arts & crafts.

Gulfshore Playhouse – Who’s Afraid of Virginia Woolf?
📅 Oct 21 – Nov 23, 2025
📍 Gulfshore Playhouse
A compelling production of the classic drama.

The Naples Players – Ada and the Engine
📅 Oct 15 – Nov 9, 2025
📍 Price Studio Theater
An engaging local theater production.

🍂 November Events

Dia de los Muertos Celebration
📅 November 1–2, 2025 (10 AM – 4 PM)
📍 Naples Botanical Garden
Cultural celebration featuring music, dance, crafts, and vibrant displays.

Music in the Garden
📅 November 8, 2025 (2 PM – 4 PM)
📍 Naples Botanical Garden, Performance Lawn
Enjoy local musicians performing amidst beautiful garden scenery.

A Veteran's Salute Concert
📅 November 9, 2025
📍 Cambier Park
Free afternoon concert honoring veterans with the Naples Concert Band.

Evening on Fifth
📅 November 13, 2025
📍 Fifth Avenue South
Monthly street festival with music, dining, and shopping.

USA TODAY Wine & Food Experience
📅 November 15, 2025 (1 PM – 4 PM; early entry 12 PM)
📍 Paradise Coast Sports Complex
Taste food and drink from local and national chefs, paired with live entertainment.

Gulf Coast Big Band Jazz Concert
📅 November 16, 2025
📍 Cambier Park
Free jazz concert supporting youth music scholarships.

Korngold's Hollywood Concerto
📅 November 20 & 21, 2025
📍 Artis—Naples
Naples Philharmonic Masterworks featuring orchestral music.

Community Day Fall Celebration
📅 November 22, 2025
📍 Artis—Naples
Free day of music and family activities with youth performances.

Igudesman & Joo
📅 November 25, 2025
📍 Artis—Naples
Comedy-meets-classical-music performance.

National Hockey Festival
📅 November 27–29, 2025
📍 Paradise Coast Sports Complex
Field hockey tournament for various age groups.

Festival of Trees & Christmas Market
📅 Mid-November 2025
📍 Various Naples locations
Holiday market featuring Christmas trees, festive goods, and entertainment.

The Naples Players – Little Women: The Musical
📅 Nov 19 – Dec 21, 2025
📍 Naples Players, 701 5th Avenue South
Musical adaptation of the beloved classic novel.

Gulfshore Playhouse – White Christmas
📅 Nov 14 – Dec 21, 2025
📍 Gulfshore Playhouse
Celebrate the holiday season with this heartwarming musical.

🌿 Ongoing Activities

• Naples Botanical Garden: Special events and beautiful fall flora.

• Corkscrew Swamp Sanctuary: Serene nature walks through the cypress forest.

• 5th Avenue South & 3rd Street South: Perfect for shopping, dining, and entertainment.

• Cars & Coffee 239: Monthly car enthusiast gatherings.

• Farmer Mike’s Fall Festival: Pumpkin patches, corn mazes, and seasonal fun.

• Artis—Naples: Continuous masterworks, concerts, and cultural events.

• Local Theater & Musicals: Regular performances at Gulfshore Playhouse and Naples Players.

Explore Naples, Florida this fall and immerse yourself in vibrant events, exciting festivals, and captivating performances.