October 2023 may be over, but the fun still rolls on in our latest weekend guide.

Autumn is in full force now with all of the lovely outdoor activities such as Oktoberfests, festivals, live music, Halloween parties, mazes, and more.

Plan your weekend by tapping on the corresponding dates below to find the best events for you and don’t forget to bookmark this page as it’ll be updated weekly!

Weekend Events for October 6ย – 8, 2023

What to Do in Naples Florida Weekend Guide - October 6 - 8, 2023 - Celebration Park
October is here and we have a jam-packed weekend of activities with Italian Fest at Seed to Table, Naples Rocktoberfest Half Marathon & 5k at North Collier Regional Park, and the 9th Annual Fall Festival & Corn Mazes at Farmer Mikes U Pick.

That’s not all though we have plenty of live music and shows including Old School at Celebration Park, Chris Franjola at Off the Hook Comedy Club, Sheena Brook at Riptide Brewing Co. and so much more below โฌ‡๏ธ

Friday, October 6th

Saturday, October 7th

Sunday, October 8th


Weekend Events for October 13ย – 15, 2023

What to Do in Naples Florida Weekend Guide - October 13 - 15, 2023 - Cars & Coffee Halloween

There’s a huge weekend ahead of us as Halloween is almost here in Naples with so many themed events including Cars & Coffee 239: Halloween Edition at Mercato, Art in the Park: Pumpkin Painting at Fleischmann Park, and Boo at the Zoo at Naples Zoo!

That’s not all though there’s non-spooky happenings too such as the Docktail Party at Naples City Dock, Thoughtful Threads Fashion Show at Food & Thought, We Love the 80’s Party at Seed to Table and so much more.

Enjoy your weekend and don’t forgot to join my Live Like a Local Naples Facebook Group for all the insider information!

Friday, October 13th

Saturday, October 14th

Sunday, October 15th


Weekend Events for October 20ย – 22, 2023

What to Do in Naples Florida Weekend Guide - October 20 - 22, 2023 - Fall Festival

Fall is in full form this weekend in Naples with October Musicfest at Mercato, 9th Annual Fall Festival & Corn Mazes at Farmer Mikes U Pick, and Truck Yeah! Food Truck Rally at Riptide Brewing Co.

That’s not all though because we also have Kountry Wayne at Off the Hook Comedy Club, The Big Bounce America at JetBlue Park, Gulf Coast Runners’ Gulf to Gulf Relay at Cambier Park and much more โฌ‡๏ธ

Friday, October 20th

Saturday, October 21st

Sunday, October 22th


Weekend Events for October 27 – 29, 2023 (Halloween Weekend)

What to Do in Naples Florida Weekend Guide - October 27 - 29, 2023 - Cars & Costumes

Things are getting a little spooky in Naples this weekend with the Halloween Spooktacular at Cambier Park, Cars & Costumes at Gulf Coast Motorworksโ , and the Barktober: Pups, Pints & Pizzaย at Oak & Stone!

Not to worry if the Monster Mash isn’t your thing, we have plenty of other great happenings too including 2023 Stone Crab Festivalย at Tin City, Carlos Mencia at Off the Hook Comedy Club, Runway 5K at Naples Airport, and so much more.

Make sure you share with me the photos if you’re going to be in costume or attend any events in this guide over on X or Instagram – have a great weekend!

Friday, October 27th

Saturday, October 28th

Sunday, October 29th


Header Photo Credit: Tamara Malaniy


Weekend Events | Naples FL | October 1 – 31, 2023

Disclaimer: Events are subject to change. Please check with the venue’s website or call to confirm.