Weekend Events in Naples, Florida for October 2023

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!

October 6 – 9 October 13 – 15 October 20 – 22 October 27 – 29

Weekend Events for October 6 – 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 ⬇️

Friday, October 6th

Food Truck Fridays 🍩 at Conservancy of Southwest Florida
Country Jam Friday 🎶 at The Hangout by Two Guys
Happy Hour 🍻 at Ankrolab Brewing Co.
Sabi Wabi 🌯 at Riptide Brewing Co. (Bonita Springs)
Kaila Love 🎶 at Seed to Table
Hat Trick 🎶 at Bone Hook Brewing Co.
Sheena Brook 🎶 at Riptide Brewing Co. (Bonita Springs)
Doggone Organic 🌭 at Riptide Brewing Co. (Naples)
Chris Franjola 🤣 at Off the Hook Comedy Club
Adult Only Trivia 🧩 at Riptide Brewing Co. (Naples)
Beginners Bachata Group Class 💃 at Allstar Dance Studio
Big Cypress Band 🎶 at Franklin Social
Sing-a-long Karaoke 🎙️ at Naples Flatbread Kitchen & Bar
Women of the 60’s 🎶 Norris Center
Radio Road 🎶 at Dogtooth Sports and Music Bar
Valerie Tyson Band 🎶 at Seed to Table
Silent Dance Party 🎧 at Millennial Brewing Company
Friday Glow-in-the-Dark Game Night 🎯 The Axe Lodge
Rod Stewart, Tom Jones, & Meatloaf Tribute Show 🎶 at The Stage Bonita
Flora Top Hits 🎶 at Jack’s Seafood Bar and Grill
DJ Joey Messina 🎶 at Seed to Table

Saturday, October 7th

Naples Rocktoberfest Half Marathon & 5k 👟 at North Collier Regional Park
Run & Swim Workout 🏊‍♂️ at Lowdermilk Beach
Croptoberfest 📔 at Hawthorn Suites by Wyndham Naples
Sand Dollar Beach Club 🐚 at Lowdermilk Beach
Fall Market & Vendors 🌽 at Vanderbilt Farmer’s Market
Farmers Market & Craft Show 🧵 at Miromar Outlets
15th Annual Bra Ride 🎗️ at Rockstar Harley-Davidson
Pet Appreciation and Adoption Day 🐾 at DeVoe Subaru of Naples
Italian Fest 🍝 at Seed to Table
Corner Spot Diner 🍔 at Riptide Brewing Co. (Bonita Springs)
No Limit Pub Poker Tournament ♠️ at Bone Hook Brewing Co.
Gypsy Blue 🎶 at Seed to Table
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
AURA 🎶 at Food & Thought 2
Old School 🎶 at Celebration Park
Swinging Bridge 🎶 at Bone Hook Brewing Co.
The Fabulous Girls of Motown Tribute Show 🎶 at The Stage Bonita
Chris Franjola 🤣 at Off the Hook Comedy Club
Social Dance 💃 at Modern Steps School of Dance
Deb & The Dynamics 🎶 at Dogtooth Sports and Music Bar
Edith Diamond 🎶 at Franklin Social
The Groove 🎶 at Seed to Table
Ben Allen Band 🎶 at South Street City Oven & Grill
Tombstone Chevy 🎶 at Jack’s Seafood Bar and Grill
DJ Mr. Nights 🎶 at Seed to Table

Sunday, October 8th

BC Girls Soccer Scramble ⛳️ at Bone Hook Brewing Co.
Mini Buddhas Kids Yoga 🧘‍♀️ at Children’s Museum of Naples
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
Muddy Princess 🏃‍♀️ at Force Center
Sunday Brunch 🍾 at The Hangout by Two Guys
Sunday Ticket 🏈 at Bone Hook Brewing Co.
Football Sunday 🏈 at Ankrolab Brewing Co.
NFL Games & Specials 🏈 Dogtooth Sports and Music Bar
Kruks Philly Steaks 🍖 at Riptide Brewing Co. (Bonita Springs)
Italian Fest 🍝 at Seed to Table
Reggae Jam 🎶 at Seed to Table
Sunday Trivia 🧩 at Bone Hook Brewing Co.
Sunday Sunset Clean Up ♻️ at Delnor-Wiggins Pass
Manhattan Connection 🎶 at Dogtooth Sports and Music Bar
Chris Franjola 🤣 at Off the Hook Comedy Club
Sunday Karaoke 🎤 at Jack’s Seafood Bar and Grill

Weekend Events for October 13 – 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

Country Jam Friday 🎶 at The Hangout by Two Guys
Happy Hour 🍻 at Ankrolab Brewing Co.
Kaila Love 🎶 at Seed to Table
Docktail Party 🚤 at Naples City Dock
Old School 🎶 at The Boardroom Tavern
Dueling Pianos 🎶 at Bone Hook Brewing Co.
Paint and Pint Night: Halloween Edition 🍺 at Riptide Brewing Co.
Becky Robinson 🤣 at Off the Hook Comedy Club
Bachata Group Class 💃 at Allstar Dance Studio
Florida Everblades 🏒 at Hertz Arena
Sing-a-long Karaoke 🎙️ at Naples Flatbread Kitchen & Bar
The Dazzling DelRays 🎶 at Dogtooth Sports and Music Bar
Remix Band 🎶 at Seed to Table
AURA 🎶 at Vicente of London
Friday Glow-in-the-Dark Game Night 🎯 The Axe Lodge
Bruno Mars Tribute Show 🎶 at The Stage Bonita
Boo at the Zoo 👻 at Naples Zoo
Moonstone Riders 🎶 at Jack’s Seafood Bar and Grill
DJ Joey Messina 🎶 at Seed to Table

Saturday, October 14th

Haunted 5K, 10K, & Half Marathon 👟 at North Collier Regional Park
Community Clean Up ♻️ at Bonita Beach Park
Cars & Coffee 239: Halloween Edition 🏎️ at Mercato
Down to Play, Up to Stretch 🐶 at Baker Park
Wildland Fire Festival 🔥 at Koreshan State Park
Sand Dollar Beach Club 🐚 at Lowdermilk Beach
Fall Market & Vendors 🌽 at Vanderbilt Farmer’s Market
Farmers Market & Craft Show 🧵 at Miromar Outlets
New Volunteer Orientation 🐶 at Collier County DAS
Mercato Pumpkin Patch 🎃 at Mercato
Art in the Park: Pumpkin Painting 🎃 at Fleischmann Park
Hand & Harvest Artisan Market 🛍 at Mercato
Thoughtful Threads Fashion Show 👗 at Food & Thought
No Limit Pub Poker Tournament ♥️ at Bone Hook Brewing Co.
Gypsy Blue 🎶 at Seed to Table
Opus One 🍷 at Naples Wine Collection
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
Docktail Party 🚤 at Naples City Dock
Old School 🎶 at Celebration Park
Dino’s Trio 🎶 at Bone Hook Brewing Co.
Abba & Mamma Mia Tribute Show 🎶 at The Stage Bonita
Femme Fatale Pink Party 🎗️ at Seed to Table
Becky Robinson 🤣 at Off the Hook Comedy Club
Social Dance 💃 at Modern Steps School of Dance
Moonstone Riders 🎶 at Dogtooth Sports and Music Bar
Extasy Band 🎶 at Seed to Table
DJ Brandi Perl & DJ Jenny Disko 🎶 at Seed to Table

Sunday, October 15th

Sunday Brunch 🍾 at The Hangout by Two Guys
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
Breathwork in the Nature 🧘‍♀️ at Sacred Soul Sanctuary
Sunday Ticket 🏈 at Bone Hook Brewing Co.
Football Sunday 🏈 at Ankrolab Brewing Co.
NFL Games & Specials 🏈 Dogtooth Sports and Music Bar
Docktail Party 🚤 at Naples City Dock
We Love the 80’s Party 🪩 at Seed to Table
Sunday Trivia 🧩 at Bone Hook Brewing Co.
Becky Robinson 🤣 at Off the Hook Comedy Club
Sunday Karaoke 🎤 at Jack’s Seafood Bar and Grill

Weekend Events for October 20 – 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 ⬇️

Friday, October 20th

Walk on the Wild Side 🥾 at Lovers Key State Park
Country Jam Friday 🎶 at The Hangout by Two Guys
The Big Bounce America 🎟️ at JetBlue Park
Happy Hour 🍻 at Ankrolab Brewing Co.
Joel Fry 🎶 at Seed to Table
Chris Bepko 🎶 at Riptide Brewing Co. (Naples)
Eden’s Earth Wind & Fryer 🎶 at Riptide Brewing Co. (Bonita Springs)
Hat Trick 🎶 at Bone Hook Brewing Co.
Kountry Wayne 🤣 at Off the Hook Comedy Club
Bachata Group Class 💃 at Allstar Dance Studio
HARDY 🎶 at Hertz Arena
Sing-a-long Karaoke 🎙️ at Naples Flatbread Kitchen & Bar
J.P. Soars & The Red Hots Live 🎶 at Dogtooth Sports and Music Bar
Entourage Band 🎶 at Seed to Table
Bullseye Glow Bingo 🎯 The Axe Lodge
Big Night Out! Dance Band 🎶 at The Stage Bonita
Psychedelic Halloween w/ Lucid Gardens 🎃 at The Oasis Naples
Soapy Tuna 🎶 at Jack’s Seafood Bar and Grill
DJ Joey Messina 🎶 at Seed to Table

Saturday, October 21st

Gulf Coast Runners’ Gulf to Gulf Relay 👟 at Cambier Park
6th Annual Run, Walk & Roll 5K 👟 at Paradise Coast Sports Complex
Spooky Fun Halloween Science Show & Cruise 👻 Pure Florida
Sand Dollar Beach Club 🐚 at Lowdermilk Beach
Fall Market & Vendors 🌽 at Vanderbilt Farmer’s Market
Farmers Market & Craft Show 🧵 at Miromar Outlets
The Big Bounce America 🎟️ at JetBlue Park
Juanchitos Grill 🌮 at Riptide Brewing Co. (Naples)
Truck Yeah! Food Truck Rally 🫔 at Riptide Brewing Co. (Bonita Springs)
Oktoberfest 🍻 at Ankrolab Brewing Co.
5th Year Anniversary 🎉 at Bone Hook Brewing Co.
No Limit Pub Poker Tournament ♣️ at Bone Hook Brewing Co.
Pets & Pints 🐶 at Riptide Brewing Co. (Bonita Springs)
Gypsy Blue 🎶 at Seed to Table
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
Sunset Saturdays: Nostaljah 🎶 at The Cove (Paradise Coast Sports Complex)
The Eagles Tribute Show 🎶 at The Stage Bonita
Kountry Wayne 🤣 at Off the Hook Comedy Club
Social Dance 💃 at Modern Steps School of Dance
Memphis Lightning 🎶 at Dogtooth Sports and Music Bar
Valerie Tyson Band 🎶 at Seed to Table
Section 8 🎶 at Jack’s Seafood Bar and Grill
DJ Zee 🎶 at Seed to Table

Sunday, October 22th

Naples Beach Yoga 🧘‍♂️ at Seagate Beach
9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
The Big Bounce America 🎟️ at JetBlue Park
Sunday Brunch 🍾 at The Hangout by Two Guys
Exhale Dance Convention 🩰 at Hilton Naples
Sunday Ticket 🏈 at Bone Hook Brewing Co.
Football Sunday 🏈 at Ankrolab Brewing Co.
October Musicfest 🎶 at Mercato
NFL Games & Specials 🏈 Dogtooth Sports and Music Bar
Ngyen Street 🍲 at Riptide Brewing Co. (Bonita Springs)
Limited Edition 🎶 at Seed to Table
Sunday Trivia 🧩 at Bone Hook Brewing Co.
Martini Russa 🎶 at Seed to Table
Sunday Sunset Cleanup ♻️ at Delnor-Wiggins Pass Park
AURA 🎶 at Food and Thought 2
Cahlua and Cream 🎶 at Dogtooth Sports and Music Bar
Kountry Wayne 🤣 at Off the Hook Comedy Club
Sunday Karaoke 🎤 at Jack’s Seafood Bar and Grill

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 Motorworks⁠, and the Barktober: Pups, Pints & Pizza 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 Festival 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!