The streets of downtown Westbury will come alive with food, music, shopping and family fun during the upcoming Westbury Spring Street Fair, set for Saturday, May 31, from 10 a.m. to 4 p.m. on Post Avenue. Organized by the Westbury Business Improvement District, the event has been a cherished community tradition for nearly 20 years, drawing visitors from across Long Island and beyond.
“We start right at the block by the train station and stretch down to The Space at Westbury Theater,” said Vanessa Esposito, executive director of the Westbury BID. “It’s one block from the train—super accessible—and that makes a big difference for people coming from out of town.”
While the street fair is well-known for its diverse mix of vendors, food stalls and live entertainment, this year’s event features a few exciting new additions.
“This spring, we’re going to have a petting zoo and pony rides, which we’ve never had before,” Esposito shared. “The petting zoo seems to be a trend with everybody I’m talking to—it’s popular and I think the adults like it just as much as the kids do.”
The event is rain or shine, with no rain date scheduled, a decision that underscores the BID’s confidence in the fair’s appeal regardless of weather. Over the years, the event has grown steadily, not only in size but also in scope, thanks largely to the BID’s promotional efforts. Esposito, who has led the organization for six years, played a key role in reinvigorating local business participation.
“When I started, I think I got most of the businesses to participate for the first time,” she said. “Before that, there wasn’t much interest. I explained that people were coming from out of town and we leaned into advertising and social media. Now, I can say pretty much all of them are involved.”
Indeed, one of the fair’s biggest draws is the chance to discover the many independent, small businesses that line Post Avenue. Westbury’s downtown is notably devoid of major chains—something Esposito attributes to the unique character of the village.
“It’s not that we don’t allow franchises—we just don’t have to,” she explained. “Even during COVID, I was nervous that we might lose businesses. But somehow, they kept their clients and we only had one store close during that whole time. We even filled that space during the pandemic with a florist. That’s how tight-knit and resilient this community is.”
With its walkable layout, cultural diversity and vibrant small business scene, Westbury’s village core stands out as a destination. The fair showcases this charm while encouraging new visitors to explore and engage.
“People don’t know about Westbury as much as they should,” Esposito emphasized. “It’s a village. It’s very condensed—just about 10 blocks—but packed with mom-and-pop shops. There’s so much character here that you won’t find in big-box towns.”
The fair typically attracts a multi-generational crowd, with families, young professionals and seniors all mingling in the festive atmosphere. Recent years have seen an increase in attendance from outside the area, thanks to targeted advertising and the convenience of the nearby LIRR station.
Esposito also noted the expansion of the street fair into a twice-yearly event, which began as a response to post-COVID outdoor demand.
“We used to only have a fall fair,” she said. “Then I thought, why not do a spring one too? It took off and now we do two fairs a year.”
As excitement builds for May 31, the BID team is working behind the scenes to ensure the fair runs smoothly. From booking entertainment to coordinating logistics for vendors, it’s a full-scale effort—but one that reflects the BID’s commitment to making downtown Westbury a thriving, visible part of Long Island’s community life.
