Season is starting to stir. The calendar is getting busier, fall events are popping up, and this week brings one of the better mixes of free concerts, farmers markets, Halloween fun, live sports, and community events we’ve seen since summer.

From Oktoberfest with FC Naples and three days of Boo at the Zoo to a free outdoor rock concert and two of Naples’ favorite farmers markets, here’s what’s worth putting on your calendar this week.

🗓️ Wednesday, October 7

⚽ FC Naples vs. Richmond Kickers — Oktoberfest Night

📍 Paradise Coast Sports Complex, 3940 City Gate Blvd. N., Naples🕖 7:00 PM

🎟 Tickets required

Soccer meets Oktoberfest as FC Naples takes on the Richmond Kickers at Paradise Coast Sports Complex. FC Naples is turning Wednesday night’s home match into an Oktoberfest celebration, making this more than just another night at the pitch. If you haven’t made it to an FC Naples game yet, this could be a fun excuse to check out Naples’ hometown professional soccer club.

🍷 Wine Down Wednesday — Seed to Table

📍 Seed to Table, 4835 Immokalee Road, Naples🕔 5:00 PM

🎟 Free to attend

Wednesday nights at Seed to Table bring live music, drinks and a lively midweek crowd. This week features Manhattan Connection at the Wine Bar, followed later in the evening by Girls Nite Out. No admission required — just expect food and drinks to be additional.

🎭 Over the River & Through the Woods — The Naples Players

📍 The Naples Players, Kizzie Theater, 701 Fifth Ave. S., Naples
🎟 Tickets required

Joe DiPietro’s popular family comedy begins its October run this week. The story follows a young man faced with a major career opportunity that would take him away from his close-knit Italian-American grandparents — who naturally have some thoughts about that. The production runs through October 25.

🗓️ Friday, October 9

🎃 Halloween Hustle 5K + Vendor Village — Baker Park

📍 Baker Park, Naples
🎟 Vendor Village open to the public

Naples is getting into the Halloween spirit Friday with the annual Halloween Hustle 5K. The race itself is sold out, but you don’t necessarily need a race bib to join the fun. The event’s Vendor Village is open to the public, making it a community option even for those who would rather cheer than run. Expect costumes, runners and plenty of early Halloween energy.

🎨 ¡ARTE VIVA! — Coco Art Gallery

📍 Coco Art Gallery at Coastland Center, 1900 Tamiami Trail N., Naples🕛 Noon–6:00 PM

🎟 Free

Need an indoor option? The Art Council of Southwest Florida’s ¡ARTE VIVA! exhibition is on display at Coco Art Gallery throughout October. The free exhibition showcases work from Southwest Florida artists and can be visited during gallery hours through November 1.

⭐ Saturday, October 10 — The Biggest Day of the Week

If you’re going to pick one day to get out of the house this week, Saturday wins. You could legitimately start with a farmers market in the morning and finish with a free outdoor concert at night.

🛍️ Third Street South Farmers Market

📍 Third Street South, Old Naples🕢 7:30 AM–11:30 AM

🎟 Free admission

One of Naples’ Saturday traditions. The Third Street South Farmers Market brings local vendors, fresh produce, baked goods, flowers, specialty foods and plenty of coffee to Old Naples. Get there early, grab something for breakfast and enjoy downtown before the day heats up.

🥕 Vanderbilt Farmers Market

📍 Galleria Shoppes at Vanderbilt, North Naples🕗 8:00 AM–1:00 PM

🎟 Free admission

North Naples has its own Saturday morning option. The Vanderbilt Farmers Market features produce, flowers, honey, baked goods, specialty foods and local vendors, with extended fall hours until 1 PM.

🎃 Boo at the Zoo — Naples Zoo

📍 Naples Zoo at Caribbean Gardens, 1590 Goodlette-Frank Road, Naples📅 Saturday, Oct. 10 through Monday, Oct. 12

🎟 Included with regular Zoo admission

One of Naples’ biggest family Halloween traditions is back — and this year you have three days to catch it. Boo at the Zoo includes trick-or-treating for children 12 and under, costumed characters, pirates, princesses, superheroes, dinosaurs, mini unicorns, live entertainment and plenty of Halloween surprises throughout the Zoo. Costumes are encouraged. Because this is one of the more popular family events of the fall, checking admission availability before heading over is a good idea.

🔬 Science Saturday — Rookery Bay

📍 Rookery Bay Environmental Learning Center, 300 Tower Road, Naples🕘 9:00 AM–4:00 PM

🎟 Included with admission

Looking for something educational for the kids? Science Saturday at Rookery Bay gives families another way to explore Southwest Florida’s environment while visiting the Environmental Learning Center. While you’re there, you can also check out the current art exhibition, Through the Light of the Estuary.

🎶 Music in the Garden — Naples Botanical Garden

📍 Naples Botanical Garden, 4820 Bayshore Drive, Naples🕑 2:00–4:00 PM

🎟 Included with Garden admission | Members free

Bring a chair or blanket and settle onto the Hoffmann Lawn for an afternoon of live music. This Saturday features Havy Rodriguez & The Miami Splash. Garden admission is currently $27 for adults and $12 for children ages 4–17. Children 3 and under and Garden members are free.

🎸 RocktoberFest 2026

📍 The Cove at Paradise Coast Sports Complex, 3940 City Gate Blvd. N., Naples🕕 6:00–9:00 PM

🎟 FREE admission

Here’s our free pick for Saturday night. RocktoberFest returns to The Cove with Rock Republic performing live outdoors. Expect rock music, German-inspired food and drinks, giveaways and an Oktoberfest atmosphere. General admission is completely free, with an optional VIP experience available separately. A pretty solid Saturday night for exactly $0 admission.

🗓️ Sunday, October 11

🎃 Boo at the Zoo — Day Two

📍 Naples Zoo
🎟 Included with regular Zoo admission

Missed Saturday? Boo at the Zoo continues Sunday with trick-or-treating, characters, entertainment and Halloween activities throughout the Zoo.

🗓️ Monday, October 12

🎃 Final Day of Boo at the Zoo

📍 Naples Zoo
🎟 Included with regular Zoo admission.

Monday is the third and final day of this year’s Boo at the Zoo weekend. If Saturday and Sunday are packed with other plans, this gives families one more opportunity to catch it.

🗓️ Tuesday, October 13

🧠 Spotlight Trivia Night — The Oasis Naples

📍 The Oasis, 1046 Pine Ridge Road, Naples🕢 7:30 PM

🎟 Free to play

Think you know everything? Prove it. Spotlight Trivia takes over The Oasis every Tuesday night, with teams competing while the restaurant’s full food and drink menu is available. No cover and free to play.

🔁 Also Happening This Week

🎨 ¡ARTE VIVA!
Coco Art Gallery at Coastland Center | Through Nov. 1 | Free

🌿 Historias del aire y del suelo
Naples Botanical Garden | Through Oct. 25 | Included with Garden admission

🎨 Through the Light of the Estuary
Rookery Bay Environmental Learning Center | Through Oct. 29 | Included with admission

🎭 Over the River & Through the Woods
The Naples Players | Oct. 7–25 | Tickets required

👀 What Did We Miss?

Naples always has something happening — and some of the best events are the little neighborhood festivals, markets and community gatherings that don't get much publicity.

Know about something happening around Naples this week that should be on our radar?

And if you're heading to one of these events, tag Naples News Now in your photos. We might just share them. ☀️