Thursday, October 1, 2026
When outlining 5-year-old Dakota Whaley’s face in paint at Freeport’s annual Nautical Festival on Saturday, Abigail Aguilar, of Freeport, paid close attention to how her brush layered the colors. When Dakota’s transformation was complete, the Island Park resident jumped up from her chair to see herself in the mirror with a butterfly across her face.
Children could be seen up and down the Nautical Mile, a.k.a. Woodcleft Avenue, with their faces painted as butterflies or tigers, while their parents perused local vendors or lined up for fried Oreos.
This year’s festivities started with a ribbon-cutting ceremony led by Freeport Mayor Robert Kennedy. The much-anticipated event is Freeport’s unofficial start to the summer season, when the Nautical Mile welcomes Long Islanders from near and far to its numerous eateries and bars, and the party and fishing boats head out to open waters.
“We’re just here to enjoy the festival and the nice weather,” said Veronica Barrera, as she kept an eye on her younger son on his scooter. “We do this every year. The kids get to play on the slides and ride their little car and scooter.”
Dana Frieda and Walsh Mulder, of Franklin Square, hung out with their 8-year-old daughter Shivon, who was cooling off with an Italian ice. “This is our first time here,” Frieda said. “We were looking for something to do outside and walk around. I think this is awesome, and I think it’s definitely something we’re going to start doing every year as a family.”
For Freeport native Craig Stegner, attending the festival means catching up with friends he has known since third grade. Before walking the Mile, Stegner stopped by the Bamboo Bar and Grill to share some laughs and the outdoor music with friends. “I’ve known these guys my whole life,” Stegner said. “It’s great to come out and have a few drinks while catching up.”
Specialty foods were offered up and down the Mile, and there were plenty of amusement rides for children of all ages. To give that island feeling, steel drum bands played, and at Sea Breeze Park, there was an impressively long lineup of acts performing at the Blues Festival, which ran in tandem with the Nautical Mile Festival.
The festival has been going strong for 31 years, Mayor Kennedy said. “Every year it’s expanding a little bit and becoming more and more of a success,” he noted. “I’m really glad to have everyone out here and really see the businesses of the Nautical Mile for the first time this season. This is definitely the launch of the summer season, and this is the fifth year post-Superstorm Sandy, and they completely rebuilt this Nautical Mile in the last five years. I am proud of them.”
