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When Vin DePasquale started a little event in which people could have fun and go by boat, he had no idea the huge spectacle it would become.

Now he’s saying goodbye to the Great Dock Canoe Race, but cherishing the memories of one of Naples’ most popular yearly gatherings.

DePasquale arrived in Naples in 1971 when it was a sleepy fishing village.

The entrepreneur was looking for something to do so he worked with a partner to create Crayton Cove with boat slips and condos. Then he redeveloped a former clam-shelling and oyster-processing plant on the Gordon River into Tin City.

In 1976, he opened The Dock restaurant and later Riverwalk at Tin City. As his first season in the restaurant business ended, DePasquale realized there wasn’t much going on during the late spring and summer season so he decided to do something about it.

Party

“It was kind of an end of season party,” DePasquale said about the first Great Dock Canoe Race. “That is what it was. It was something to sign off from the season. In 1976, we knew little about the end of season. April came and Easter came and there was nothing on the streets, and we weren’t prepared for that so the following year we created a canoe race. It was to bring about all the restaurant owners and staff to celebrate the end of season.

“It became such a fun event that people wanted us to do it again and it just took off and then it became a community event,” he said. “As a community event we had to get a little more serious about it and put some rules into it. Who thought about that?”

The outing went from some fun with canoes and munching on oysters to a contest with categories, rules and themes.

One of DePasquale’s favorite memories is when the race added themes each year.

“One of the turning points in the past years was when we became so competitive with our racing that we had to add themes to it to put the fun back in it,” he said.

The three-mile race always started and ended at The Dock. This year’s theme was “The Last Dance,” a play on both the last race and the disco era when the canoe race spawned.

Look back

As he organized the very last Great Dock Canoe Race, DePasquale looked back on his 40 years running the event, sharing his favorite stories and memories.

“Early on when we started doing this — two to three years into doing this — we had a team that was not taking this very seriously and then they started to race,” DePasquale began. “They had a cooler in the middle of the canoe with iced beers. They did the race and they came back kind of lounging. As they crossed the finish line they lifted up the cooler and there was a motor in the bottom of the canoe. Of course, they were disqualified.

“And the broken paddle award came about with the first race where someone finished with a broken paddle and that became our good sportsmanship award,” DePasquale said.

Another happy memory is giving back to the community.

“We always provide a $5,000 grant for kids in the community for children’s programs that need a little kick,” he explained. “Sometimes the theme ties in with the charity. A few years ago The Hunger Games was the theme and the charity was the harvest program. That is fun. We sit around and each October or November and brainstorm these things.”

Naples Mayor Bill Barnett moved to Naples in 1973 and has seen the Great Dock Canoe Race grow and prosper.

“It’s been amazing what he (Vin) and his family have done for the community,” Barnett said. “You would need more than a short article to say it all. They built a legacy with the Great Dock Canoe Race.”

Barnett said DePasquale’s work has gone beyond his boating contest.

“He has been so involved in the Naples community,” Barnett continued. “You can’t mention his name to anyone who has been here for a while without putting a smile on their face. He built his own legacy with this.”

After 40 years, DePasquale said it is time to end his era with the race.

Let go

“We have done it for 40 years and this is an event we do ourselves,” he said. “We have up to 50 volunteers so it is a big endeavor. Sometimes it is good to let go of these things and see if someone picks it up.”

While he is ready to let go of all the work, he is nostalgic and a bit saddened by the ending.

“There is a great deal of fun and satisfaction when you don’t plan on these things and they just happen,” DePasquale said. “The community has been terrific. Hundreds of thousands of people over 40 years have turned out to see this. We will certainly miss the excitement of that. This has reached out in the community like nothing I have seen before.

“The one thing we are proud of,” he said, “is we have been there and we helped create this. We are proud to have created more fun on the water in Naples. We have really enjoyed doing this. This is bittersweet.”

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