Englewood’s Annual Waterfest – A Celebration of Everything Water

Englewood has long drawn folks interested in fishing, boating, and water recreation opportunities. Their biggest festival, Englewood Beach Waterfest, celebrates the community's liquid assets with activities ranging from educational exhibits to powerboat racing. The event is divided into three main portions – the Pirate Poker Run, the Paddle for the Pass, and Racefest – each celebrating the waters of the laid-back Gulf community in a unique way.

Pirate Poker Run: Arrrr you ready to hit the seas and play the river?

September 11-12, 2026

The Englewood Waterfest kicks off with the Pirate Poker Run. Grab your band of buccaneers, don your eye patch, and take to the seas for a heist on the high seas. Teams race to the seven predetermined Englewood locations to retrieve doubloons, er poker chips, of various hues. By ship is the most authentic, but landlubbers can traverse by car or motorcycle. Once the booty is gathered, participants race to the Lighthouse Grill and ante up for a game of Pirate Poker. The top prize is $500, which can buy a mighty large barrel of rum.

Yo-ho-ho! After the game, partake in a tankard or two at the after party. Contests for the best pirate-themed boat and pirate costume keep the swashbuckling flowing as sea yarns of the day’s adventures are told and, perchance, embellished to the point of infamy.

Tickets for the Pirate Poker Run can be purchased in advance online, at the Captain’s Party at the SandBar Tiki & Grille the night before the seafaring scavenging, or at The Backyard at Skip’s Marina before the ships depart the for the high seas.

Paddle for the Pass Community Clean Up: Spend the morning primping Mother Nature

October 3, 2026

The Englewood Beach Waterfest is equal parts fun and environmental conservation. The Paddle for the Pass encourages the community to come together to clean up the beloved waters that make Englewood so special. Participants can choose to volunteer by kayak, paddleboard, or canoe – bringing personal vessels or using one provided by the event – by foot on the beach, or on the water using their own boat. Meeting at Stump Pass Beach State Park, individuals, teams, and families collaborate to “celebrate environmental stewardship, boating safety, and our shared commitment to preserving one of Southwest Florida’s most treasured coastal ecosystems.”

While paddling, boating, or walking along the waters of Englewood, watch for diving birds, manatee, dolphin, crabs, and sea turtles and know that every bit of plastic, cigarette butt, or lost flip flop removed from Lemon Bay will make it safer for them to live.

Register online to sign up and note the desired role and vessel. Water, light refreshments, and all necessary clean up supplies provided.

Racefest: A weekend-long whirlwind celebration of community, fun, and really, really fast power boats

October 8-12, 2026

Thursday: On your marks, get set, go! Starting with the Power Up Pre-Race Party Thursday night, Racefest weekend is officially underway! Listen to live music, nosh on great food, and get savvy to the teams of this weekend’s main event.

Friday: Get the engines revving by participating in the Inflated Invitational Beach Race. Don your favorite inflatable costume and meet up at Englewood Beach at 10am for this annual 100-yard dash. As it is turtle nesting season, race organizers ensure no structures or turtle nesting zones are affected by the race. Friday night is the Waterfest Block Party, a free event on Dearborn Street, full of music and food. Attendees have the rare opportunity to inspect the boats up close (once they’re in the water, they move too fast to truly “see” these incredible vessels) and meet their need for speed drivers. Pick a favorite to root for the next day!

Saturday-Sunday:  – the APBA Offshore National Championship. Enter Waterfest Village and watch as some 40 to 50 boats zoom through the water at speeds over 150 miles per hour. Awe as they zip by, all hoping to win the $50,000 race purse. Multiple races of various classes are held on Saturday and Sunday, culminating with the Awards Ceremony on Sunday evening at the SandBar Tiki & Grill.

Simultaneously with the races, the Family Conservation Center educates and entertains guests about the waters on which the boats are racing. From 10am-4pm, the interactive Conservation Village features 2,400 square feet of exhibits about sharks, manatees, reefs, conservation, and marine life, all in partnership with Mote Marine, SWFL Sea Turtle Rescue, Butterfly Encounter, and more. Access to the Family Conservation Center is included in the Waterfest ticket.