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 6 – 8, 2023
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
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
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)
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!
Friday, October 27th
- Country Jam Friday 🎶 at The Hangout by Two Guys
- Happy Hour 🍻 at Ankrolab Brewing Co.
- Joel Fry 🎶 at Seed to Tabl
- 2023 Stone Crab Festival 🦀 at Tin City
- Thunder Beach 🎶 Miromar Outlets
- Sunset Wine Cruise 🚢 at Naples Princess Cruises
- Lineup Band 🎶 at Bone Hook Brewing Co.
- Trunk or Treat 🍭 at The Florida Sports Park
- Carlos Mencia 🤣 at Off the Hook Comedy Club
- Bachata Group Class 💃 at Allstar Dance Studio
- Sing-a-long Karaoke 🎙️ at Naples Flatbread Kitchen & Bar
- Deb & The Dynamics 🎶 at Dogtooth Sports and Music Bar
- The Groove 🎶 at Seed to Table
- AURA 🎶 at Vicente of London
- Friday Glow-in-the-Dark Game Night 🎯 The Axe Lodge
- Greatest Guitar Players Tribute Show 🎶 at The Stage Bonita
- Torched 🎶 at Jack’s Seafood Bar and Grill
- DJ Joey Messina 🎶 at Seed to Table
Saturday, October 28th
- Runway 5K 👟 at Naples Airport
- Hoots & Hisses Halloween Celebration 🎃 at Conservancy of Southwest Florida
- Paws and Pumpkins 🐾 at Baker Park
- Farmers Market & Craft Show 🧵 at Miromar Outlets
- Yoga in the Beer Garden 🧘♀️ at Ankrolab Brewing Co.
- Cars & Costumes 🏎️ at Gulf Coast Motorworks
- Hand & Harvest Artisan Market 🛍 at Mercato
- Barktober: Pups, Pints & Pizza 🐶 at Oak & Stone
- Trunk-or-Treat 🍭 at Ave Maria Town Center
- Halloween Spooktacular 👻 at Cambier Park
- Gypsy Blue 🎶 at Seed to Table
- 9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
- 2023 Stone Crab Festival 🦀 at Tin City
- Ralph Curtis 🎶 at Bone Hook Brewing Co.
- 80’s Halloween Party 🎃 at Cavo Lounge
- Journey Tribute Show 🎶 at The Stage Bonita
- Halloween Bash 2023 👻 at Seed to Table
- Carlos Mencia 🤣 at Off the Hook Comedy Club
- Nightmare on Old 41 👻 at Ceremony Brewing
- Halloween Party 🎃 at Ankrolab Brewing Co.
- A Nightmare on Imperial 👻 at Jack’s Seafood Bar and Grill
- Social Dance 💃 at Modern Steps School of Dance
- Halloween Costume 🎃 at Dogtooth Sports and Music Bar
- Cameo Band 🎶 at Seed to Table
- Night to Dismember 🪓 at The Axe Lodge
- The Deplorables 🎶 at Jack’s Seafood Bar and Grill
- Mr. Mitch 🎶 at Seed to Table
Sunday, October 29th
- Adopt a Road Clean Up ♻️ at Gordon River Greenway
- SUP Yoga 🏄♀️ at Clam Pass Beach
- Naples Beach Yoga 🧘♂️ at Seagate Beach
- Sunday Brunch 🍾 at The Hangout by Two Guys
- 9th Annual Fall Festival & Corn Mazes 🎃 at Farmer Mikes U Pick
- Sunday Ticket 🏈 at Bone Hook Brewing Co.
- Football Sunday 🏈 at Ankrolab Brewing Co.
- NFL Games & Specials 🏈 Dogtooth Sports and Music Bar
- Kid’s Halloween Painting on Canvas 🎨 at Docks by Jen
- Fall Trunk & Treat Party 🍭 at Golden Gate Assembly
- 2023 Stone Crab Festival 🦀 at Tin City
- Manhattan Connection 🎶 at Dogtooth Sports and Music Bar
- Carlos Mencia 🤣 at Off the Hook Comedy Club
- Halloween Havoc Latin Jam 👻 at Seed to Table
- Sunday Karaoke 🎤 at Jack’s Seafood Bar and Grill
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.