Thursday, October 1, 2026
Dozens of decorated boats, a towering Christmas tree and hundreds of spectators brought holiday spirit to Freeport’s Nautical Mile during the village’s annual holiday boat parade and tree lighting on Saturday.
The evening began along Woodcleft Avenue at 6:30p.m. with the lighting of a 40-foot Christmas tree at the esplanade, followed by the illuminated boat parade along the Nautical Mile.
Seasonal music, an ice-sculpting demonstration, free rides, and hot chocolate and warm pretzels added to the festive atmosphere.
Elizabeth Comerford, the village’s recreation supervisor, said the tree lighting drew a strong community turnout and relied on coordination across several different village departments.
“It was a great crowd,” Comerford said. “We got a couple of people to donate their time with coffee and chocolate and cookies and pretzels. We made sure Santa arrived with the fire truck. The fire department was involved.”
Comerford added that the planning effort included “all the different departments in the village,” singling out the Department of Public Works, electric department, and the police and fire departments.
She also credited village leadership for making the annual event a huge success, saying Freeport Mayor Robert Kennedy “was very helpful.” In addition, the holiday festivities were extremely gratifying to organize, she said.
“It’s rewarding to see so many happy families,” Comerford said. “Just to get the community together in a positive event, show three, four, in such a positive light, with the beautiful Nautical Mile, the beautiful parade.”
Mayor Kennedy said the boat parade has continued to grow in size and popularity over the years.
“I’d estimate we had more than 50 boats in the parade,” Kennedy said. “It just gets bigger and bigger every year.”
He estimated attendance at around 500 spectators near the esplanade alone.
“That was just in the area near the esplanade,” Kennedy said in a statement. “There were people lined up along the canal.”
Kennedy said several additional features this year helped elevate the experience.
“This year, we added free rides and hot chocolate and warm pretzels, which I saw a lot of people enjoying,” he said. “The weather was nice. Everything just fell into place to make this another beautiful event on the Nautical Mile.”
The event also featured Santa Claus distributing toys to children, with assistance from Toys for Tots and the Freeport Police Department.
“As the boating capital of the Northeast, it just makes sense that we’d have one of the largest boat parades on Long Island,” Kennedy said. “You could see on all the children’s faces how happy they were. That’s what it really is all about, sharing this time with the children and the families.”
Ken Dookram, president of the Freeport Chamber of Commerce, highlighted the tree lighting and community partnerships that helped make the night a success.
“It was a great night, and the Christmas tree lighting was really special,” Dookram said. “That was a massive 40-foot tree.”
Dookram thanked Comerford for organizing the event, while noting a new holiday tradition.
“This was the first year that Santa gave out toys, and it was a nice way to go into the holiday season with children with smiling faces,” he said.
He also thanked community partners who supported the chamber’s hot chocolate booth.
“I also would like to give a special thanks to the Woodward School, Sparkle on Stage and Long Island Water Taxi for their help with the chamber’s hot chocolate booth, which I think everyone appreciated by the end of the evening,” Dookram said.
As boats adorned with lights paraded down the waterway and families gathered along the Nautical Mile, the annual celebration once again brought Freeport together to kick off the holiday season.
