In the past four years, the Syosset Street Fair has expanded its reach beyond Jackson Avenue. It is now closing a portion of Underhill Road to accommodate over 200 vendors and up to 10,000 attendees.
The fair, a 20-year tradition, will return on Sept. 14 from 10:00 a.m. to 5:00 p.m. and will offer food, drinks, games, and activities.
“It makes me feel good that we’re doing a lot for the community,” said Russell Green, the president of the Syosset-Woodbury Chamber of Commerce, which organizes the festival.
Green moved to the area in 1999 and said he remembers attending the street fair in the early 2000s before he joined the chamber. In 2019, Green joined the chamber’s street fair committee, which is now chaired by Tami Racaniello.
With the exception of 2020, when the festival was cancelled due to the COVID-19 pandemic, Green said the event has continued to grow each year since then. In 2021, many chambers cancelled their street fairs due to uncertainties around the state’s COVID-19 restrictions. Green said the Syosset-Woodbury chamber decided to plan the event as usual, and by the time September came around, the restrictions had lifted.
“And that’s where it was incredibly successful because a lot of other chambers and organizations had already decided they weren’t going to do outdoor events that year… I think that helped bring a lot of attention to Syosset,” he said.
He said the 2021 event was “lightyears more attended” than previous ones, welcoming attendees from all over the area. Since then, he said the momentum has kept going. Green said the street fair has seen such high attendance from visitors and vendors that the chamber has begun to close additional roads.
“When I first became the president of the chamber [in 2021], we were taking up a decent part of Jackson Avenue. And now we’ve taken Underhill too. So we’ve closed Underhill all the way down to Queen Street, and it’s filled,” he said.
Green said an additional soundstage was added to the festival, which will accommodate additional performances from local bands youth groups.
Green said the chamber is able to put on the event with help from its sponsors. This year, he noted that all sponsorship positions sold out, with Rallye Motors and SRG Residential acting as its anchor sponsors. Green said his own company, RPG Wealth Management, serves as a sponsor for the event and hires a man on stilts every year.
Green said that the man on stilts is a now-staple at the yearly festival, and that many of the attendees come to Green’s booth to comment on it. He said his favorite part of the street fair is hearing everyone’s feedback.
Green said that while an exact headcount isn’t possible, as no tickets are required for entry, the chamber expects to welcome 8,000 to 10,000 attendees this year.
“Last year was huge. And with this year, I’m expecting a huge event again,” he said.
