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Labor Day Regatta celebrates its 75th year under sail

The 75th Annual Labor Day Regatta will be held Sep. 2 and 3.
The 75th Annual Labor Day Regatta will be held Sep. 2 and 3.
Courtesy photo
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As the public gathers on the shores to view the Annual Labor Day Regatta, many viewers can often be heard reminiscing about their childhood experiences in the event, which dates back to 1946, said Regatta Chair Dave Hillmyer.

Held by the Sarasota Sailing Squadron, the event, which the organization says is the oldest continually held regatta in the southeast, will host competitors ranging from 7 years old, to about 70, during its 75th anniversary this year on Sep. 2-3.

Canceled only three times in its history, the event maintains a steady popularity, drawing clubs from across Florida from areas like St. Petersburg, Davis Islands in Tampa, more distant locations such as Jacksonville, and even some individuals from other states. 

“Everybody just knows about this regatta,” Hillmyer said. “This is such a historic sailing venue.”

Calling sailors young and old

While the regatta originally featured about 50% adults, the last few years have been youth-focused, with about 150 kids signed up out of 175 competitors this year, Hillmyer said. 

He said the occasion, which involves four different race courses in the bay, as well as racing closer to shore for the youngest participants, holds particular importance for youth.

For some younger people, it’s the first regatta of the school season, while for other kids, it may be their first regatta ever.

“This is the first time that they get to put their skills to the test on the water,” he said. “It’s kind of a big deal.”

Kay Brunsvold gets ready to set sail in the 68th annual Labor Day Regatta.
File photo

Dave Hillmyer and his wife Donna Hillmyer, who have both been involved with the club since about age 10, are no strangers to youth sailing, but they've also had the chance to watch other participants enjoy an experience similar to their own.

“We watch these kids like we follow them throughout their lives,” Donna Hillmyer said. 

Yet the event excites adults as well; an inaugural sailing event, of sorts, for the fall season, it follows the relative lack of activity during the heat of summer, Dave Hillmyer said.

What really makes the event special, said Hillmyer, is the amount of volunteers it receives. 

None of the individuals assisting with the event, which includes about 40 on the water and 100 on land, are paid, he said. 

Volunteers will staff the 15 to 16 support powerboats and will also help on shore through activities like serving food and drinks, monitoring parking, or taking out trash. 

He believes participants will have a pleasant experience out on the bay or at the squadron's clubhouse on City Island, where it has leased the land from the city of Sarasota.

“Out in the middle of the bay, you don't see a lot of boat traffic, so it's really nice,” he said.

He said members have even camped out at the clubhouse site in the past. 

“I think people find it very comfortable here because we have such a low- key atmosphere."

Although there are other labor day events, such as a Labor Day night race on Davis Islands, the Sarasota event holds a special meaning for the public, he said.

“Everybody knows if you say 'the Labor Day Regatta' in Florida, it means Sarasota Sailing Squadron."

Donna and Dave Hillmyer
Photo by Ian Swaby 



Ian Swaby

Ian Swaby is the Sarasota neighbors writer for the Observer. Ian is a Florida State University graduate of Editing, Writing, and Media and previously worked in the publishing industry in the Cayman Islands.

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