The fall season in Venice is heating up, and Venice Nights has your ultimate guide to the biggest shows, festivals, and waterfront parties happening this October and November. From reggae takeovers and Tropic Rock sunsets to Halloween madness and veterans’ tributes, here’s your hit list of must-attend events.
October 2 – Reggae Nights Pre-Party
📍 Casey Key Mainland Resort, Osprey | 5–8 PM
Season is almost here, and we’re kicking it off right. The official Reggae Nights Pre-Party lands at Casey Key Mainland with Tropic Rock vibes by Tyler Giddens. Cold drinks, waterfront views, and the best sunset spot in Venice make this the perfect launch for a packed fall schedule.
October 4 – Reggae Nights on the Island
📍 Centennial Park, Downtown Venice | 2–10 PM
The one you’ve been waiting for. Reggae Nights on the Island shuts down Tampa Avenue with a full day of music featuring Matt & Zack, Ichroniq, Undercover Rasta, and Collé Kharis. Stay in Venice’s best resort, walk to the park, and make it a weekend to remember. Venice is quickly becoming Florida’s reggae capital — don’t miss this.
October 4 – Meet & Greet at Daiquiri Deck
📍 Downtown Venice
When the park goes quiet, the party keeps moving. Head to Daiquiri Deck for the official after-party meet & greet. Grab the famous chicken nachos (queso on the side), order a daiquiri with a floater, and hang with the bands. Venice Nights = music, food, and community.
October 5 – Sunday Funday
📍 Yucatan Waterfront, Matlacha | 4–7 PM
Make the short drive to Matlacha and keep the vibes alive with Tyler Giddens on the waterfront stage. Drinks, sunsets, and island grooves — Sunday done right.
October 9 & 16 – Tropic Rock Thursdays
📍 Casey Key Mainland, Osprey | 5–8 PM
Every Thursday, Casey Key Mainland turns into Tropic Rock central. Lie’d Back sets the soundtrack for coastal happy hours with smooth reggae and beachy vibes. Thursdays are locked in Osprey.
October 12 – Double Shot Sunday
📍 Yucatan Waterfront + Casey Key Mainland
Two stages, two shows, one Sunday. Aaron Kelly kicks off in Matlacha, while Smokey Lynn brings it home at Casey Key Mainland.
October 17–19 – Sun Fiesta
📍 Downtown Venice
It’s Venice’s biggest tradition: Sun Fiesta. Parades, food vendors, live music, and streets packed with locals and visitors alike. Three days of sunshine and celebration.
October 19 – Triple Reggae Sunday
📍 Matlacha + Twisted Fork, Port Charlotte
Clear your schedule — this is massive. Joseph Orchulli in Matlacha, then over to Twisted Fork for Phoenix 5 and reggae legend Mighty Mystic. This night is history in the making for Southwest Florida reggae.
October 23 – Casey Key Reggae
📍 Casey Key Mainland, Osprey | 5–8 PM
Smokey Lynn returns for a Thursday night reggae session. Nothing beats live music with a coastal breeze.
October 25 – Venice Nights Market & Music
📍 Maxine Barritt Park, Venice
Fall vibes on the water with vendors, food, and live music. Aaron Kelly opens at 5, followed by Lei’d Back at 7. Bring the family, shop the market, and dance under the stars.
October 26 – Sunday Double Dip
📍 Yucatan Waterfront + Casey Key Mainland
Another split Sunday — wherever you end up, live music is waiting.
October 30 – Tropic Rock Thursday
📍 Casey Key Mainland, Osprey | 5–8 PM
Bryan Smith closes out October on the Casey Key stage.
October 31 – Halloween in Venice
📍 Hotel Venezia
Venice Nights takes over Hotel Venezia for the ultimate Halloween party. Costumes, reggae, and a late-night dance floor featuring Bryan Smith, Off the Road, and Goodies. If you’re asking “what’s the move for Halloween?” — this is it.
📍 Nomad’s Cantina – BAT2025
Meanwhile, Nomad’s Cantina hosts Beats and Treats with Indigo I and The Trees of Life. This is your reggae warm-up party before the big night.
November 8 – For Vets, By Vets
📍 Centennial Park, Venice
A festival with heart. For Vets, By Vets is a full day of reggae, food, and community honoring those who served. One of the most meaningful events of the season.
November 15 – Venice Nights Market & Music
📍 Maxine Barritt Park, Venice
Back at Maxine Barritt for round two — even bigger. Hundreds of vendors, thousands of people, reggae and rock on the water. Venice comes alive under the November moon.
Venice Nights Highlights
- Daiquiri Deck Meet & Greet – Food, drinks, and bands up close.
- Casey Key Sundays – Second and fourth Sundays at the resort.
- Tropic Rock Thursdays – Every Thursday (except Oct. 2) at Casey Key Mainland.
This fall, Venice Nights is more than an event calendar — it’s the heartbeat of the Gulf Coast. From reggae legends to local stars, waterfront sunsets to all-night Halloween parties, the vibe is here, and the community is ready.