May 28, 2026 · Updated May 28, 2026
June arrives on Long Island with a tightly stacked calendar: a Juneteenth festival in Hicksville with 60-plus vendors, a Star Trek convention in Hauppauge, an 18-and-over night market in Syosset, a North Fork wine week, Long Island Pride in Huntington Village, and a three-day strawberry festival in Mattituck. Here is what is worth planning for.
June is the strongest month on the Long Island events calendar before August takes over, and the first few weekends are already stacking up. From a Star Trek convention in Hauppauge and a Juneteenth festival drawing 60-plus vendors in Hicksville to a wine week spread across the North Fork and Long Island Pride returning to Huntington Village, there is something worth showing up for nearly every weekend. Six events to put on the calendar now.
June 1–7 | Multiple North Fork tasting rooms, Route 25 corridor
The North Fork vineyard corridor launches its summer season with a week built specifically for people who live on Long Island year-round. Participating wineries along the Main Road corridor between Mattituck and Greenport offer deals and exclusive tasting experiences for area residents, with programming running daily through June 7. The North Fork Wine Council organizes the event each year. No single pass covers the entire week. Check liwines.com for the list of participating tasting rooms and their individual promotions before picking a route.
Saturday, June 6, 4 p.m. to midnight | Long Island Sports Hub, 1 Sports Hub Ln., Syosset
An 18-and-over evening market for handmade crafts, vintage goods, curiosities, and specialty edibles, Moonlight Market runs from late afternoon into the early hours at the Sports Hub in Syosset. The event draws vendors from across the region and has sold close to capacity in prior years. Tickets are available on Eventbrite; buying in advance is recommended. The Sports Hub sits just north of the Long Island Expressway at Exit 41N.
Sunday, June 7, 4 to 7 p.m. | The Nutty Irishman, 212 Main St., Farmingdale
Three bands take the stage at Farmingdale's Nutty Irishman Sunday afternoon for a set organized to benefit a local charitable organization. Every dollar raised during the three-hour show goes toward the fundraising total. The format is a giving event staged as a concert, not a ticketed show. Check the venue's Facebook and Instagram pages for the specific lineup and the cause being supported this cycle.
Sunday, June 14, noon to 5 p.m. | Huntington Village, Huntington
Long Island's annual pride festival returns to Huntington Village for five hours of live entertainment, a vendor marketplace, a family area, and a beer and wine garden. A parade moves through the village's main commercial blocks before the festival opens to the public. The event is free and typically draws several thousand attendees. Street parking on Main Street fills by noon; the Huntington LIRR station is a short walk from the festival grounds on New York Avenue.
June 12–14 | Hyatt Regency Long Island, 1717 Motor Pkwy., Hauppauge
The annual Star Trek and science fiction convention occupies the Hyatt Regency in Hauppauge for three days of panels, podcasters, photo opportunities, and an in-person vendors room that has already sold out. Announced guests include Nana Visitor, who played Colonel Kira Nerys across seven seasons of "Star Trek: Deep Space Nine." The convention is organized by Library for the Kind, a nonprofit supporting diversity and inclusion in children's literacy programs. Single-day and weekend passes are available at treklongisland.com.
Saturday, June 20, noon to 6 p.m. | 125 John St., Hicksville
Co-organized this year by Black Legacy Partners and the NAACP Hempstead Branch, the island's largest Juneteenth celebration brings more than 60 vendors and food trucks to a venue steps from the Hicksville LIRR station. Live performances run throughout the afternoon. This year's event doubles as a Father's Day marketplace, with shopping curated around gifts and experiences aimed at men, given the timing one day before Father's Day on June 21. Admission is free. The Hicksville station sits on the Main Line between Jamaica and Farmingdale, making it reachable from both Nassau and Suffolk.
For a full calendar, longisland.com/events and discoverlongisland.com publish updated listings through the end of summer. Patch.com's per-town event calendars are the most reliable source for last-minute additions and cancellations.
