October 2025
Oct 25
3:00 pm - 5:00 pm2025 Halloween Spooktacular and Porsche Naples Trunk or Treat
On the Saturday before Halloween, located in Cambier Park, fun events for families and children, including live music, street dancing, costume contest, games, and more. Evening on 5th to follow from 5:00 pm to 8:00 pm
Oct 25
5:00 pm - 8:00 pmHalloween Spooktacular Evening on Fifth Powered by Porsche Naples
An array of live musical performances up and down the sidewalks of 5th Avenue South, plus dining, shopping, and more following Halloween Spooktacular fun events from 5:00 pm to 8:00 pm
Oct 31
6:30 pm - 9:30 pmHalloween Night Evening on Fifth Powered by Porsche Naples
A special Halloween inspired Evening on Fifth with a spooky array of live musical performances up and down the sidewalks of 5th Avenue South, plus dining, shopping, and more.
November 2025
Nov 8
10:00 am - 4:00 pmFine Arts & Craft Show
Naples Artcrafters is a vibrant association of artists and craft artisans that hosts six major fine art and craft shows from November through April.
Nov 9
2:00 pm - 4:00 pmNaples Concert Band
A Veteran’s Salute With Guest Vocalist: Heather Ivy
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.Nov 13
6:30 pm - 9:30 pmEvening on Fifth: Powered by Porsche Naples
An array of live musical performances up and down the sidewalks of 5th Avenue South, plus dining, shopping, and more.
Nov 16
2:00 pm - 3:45 pmGulf Coast Big Band Jazz Concert
The Gulf Big Band has been performing at the Cambier Park bandshell for more than 30 years. Money is raised for local youth jazz scholarships.
Nov 29
10:00 am - 4:00 pmArt in the Park
A Naples tradition since 1957, these curated one-day events attract and support local and regional artists.
Nov 30
2:00 pm - 4:00 pmNaples Dixieland Jazz Band
The Naples Jazz Society, Inc. was founded in 1995, for the purpose of sponsoring, preserving, and promoting jazz music in southwest Florida.
December 2025
Dec 4
10:00 am - 5:00 pmGifted! A Holiday Party & Boutique
On the 4th, a ticketed cocktail party with wine, appetizers, seasonal music, and vendors offering gift items for the holiday season. Friday will be open to the public and feature the same boutique plus additional booths.
Dec 5
6:00 pm - 6:30 pmChristmas Tree Lighting Ceremony
Dec 5
5:00 pm - 10:00 pmChristmas Walk and Avenue Dining 2025
The biggest Christmas showcase in Naples! Enjoy the official Christmas tree lighting on 5th Avenue South in Sugden Plaza and amazing holiday experiences, including a living nativity by the First Church of the Nazarene, skating rink, live music, Santa Claus and Avenue dining. Two- Day Festival.
Friday, December 5 , 5 pm to 10 pm / Christmas Tree lighting ceremony on Friday the 5th beginning approximately 6 pm.
Saturday, December 6, 10 am to 10 pm
Dec 7
2:00 pm - 4:00 pmNaples Concert Band
Ring In The Season With Guest Vocalist: Steven Calakos
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.Dec 9
6:30 pm - 8:00 pmChristmas Parade
The spectacular march begins on Broad Street South and finishes on 8th Street South
Dec 11
6:30 pm - 9:30 pmEvening on Fifth: Powered by Porsche Naples
An array of live musical performances up and down the sidewalks of 5th Avenue South, plus dining, shopping, and more.
Dec 12
6:30 pm - 9:30 pmTuba Christmas
A remarkable evening of music in Sugden Plaza from sousaphone, euphonium, tuba, and baritone horn players.
Dec 13
10:00 am - 4:00 pmFine Arts & Craft Show
Naples Artcrafters is a vibrant association of artists and craft artisans that hosts six major fine art and craft shows from November through April.
Dec 14
3:30 pm - 6:30 pmChanukah Festival
The Chabad Jewish Center of Naples hosts a Chanukah celebration at Cambier Park
Dec 19
5:30 pm - 8:00 pmHOPE4KIDS Candlelight Christmas Carols
The annual event is a joyful and fun occasion for couples, families, and anyone interested in enjoying sounds of the season.
Dec 21
2:00 pm - 3:45 pmGulf Coast Big Band Jazz Concert
The Gulf Big Band has been performing at the Cambier Park bandshell for more than 30 years. Money is raised for local youth jazz scholarships.
January 2026
Jan 18
2:00 pm - 4:00 pmNaples Concert Band
Gershwin Favorites With Saxophonist: Stephen Parker
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.
February 2026
Feb 7
10:00 am - 4:00 pmCars on Fifth 2026
Feb 15
2:00 pm - 4:00 pmNaples Band Concert
Mello Tones With Guest Trombonist: Robert Kastner
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.
March 2026
Mar 15
2:00 pm - 4:00 pmNaples Band Concert
Broadway Selections With Guest Vocalist: Jodi Keogan
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.
April 2026
Apr 12
7:00 pm - 9:00 pmNaples Concert Band (a special evening performance)
A Rousing Evening With Guests: The Flourish of All-Star Middle School Trumpet Players from Collier and Lee Counties
For over 50 years, the Naples Concert Band has been a source of joy, inspiration, and connection in our community.
