1. Port Jefferson Station Community event
When: Saturday, May 16th at 11 AM
Where: Three Roads Plaza, 1029 Rt 112, Port Jefferson Station, NY
Join us for a fun-filled free community event at the Three Roads Plaza Shopping Center in Port Jefferson Station! Hosted by 7-Eleven, Alice's, Bageliscious, and other local shops in collaboration with the Port Jefferson Station/Terryville Chamber of Commerce, this exciting event will feature live music by Gregory Keller and Zuppo, a bounce house, giveaways, and free food for everyone to enjoy. Bring your family and friends for a day of community fun — all are welcome!
2. Family Fun Night at the Museum
When: Saturday, May 16th at 6 PM
Where: Long Island Children's Museum, 11 Davis Ave, Garden City, NY
Get ready for an unforgettable evening of family fun at the Long Island Children’s Museum! Join us for a special after-hours Family Fun Night filled with interactive exhibits, music, dancing, and hands-on activities for kids and caregivers to enjoy together. Families will have the chance to meet special guest author Malcolm A. Dill during a lively read-aloud storytime and creative activity, and children will receive a free copy of Marvin’s First Pet while supplies last. Guests will also enjoy dinner, raffles, exciting prizes, and full access to the museum’s engaging exhibits in a fun, safe, and welcoming environment designed to create lasting memories for the whole family.
3. Spring Farm Festival
When: Saturday, May 16th at 12 PM
Where: Smithtown Historical Society, 239 Main St, Smithtown, NY
Celebrate the season at the Spring Farm Festival at the Smithtown Historical Society! Enjoy a fun-filled day featuring local crafters, friendly farm animals, hands-on learning experiences, delicious food trucks, and live music for the whole family to enjoy. Come explore the farm, connect with the community, and make lasting springtime memories at this festive outdoor event.
4. Cradle Con 2026
When: May 16 - 17, 2026
Where: Cradle of Aviation Museum, Charles Lindbergh Blvd, Garden City, NY
Get ready for an unforgettable day of fandom fun at Cradle-Con, Long Island’s non-profit comic, collectible, and pop culture convention hosted by the Cradle of Aviation Museum. Built by fans for fans, this exciting event celebrates all things comic book culture with local comic creators, collectible vendors, cosplay gatherings, retro gaming, and activities for all ages. Whether you're a comic reader, collector, gamer, or simply looking for a fun family outing, Cradle-Con offers a welcoming and energetic experience where fans can connect, explore, and celebrate the worlds they love together.
5. Rooted: A Local Spring Festival
When: Saturday, May 16th at 10 AM
Where: Downtown Wading River, 2 Sound Rd, Wading River, NY
Join the community for Rooted: A Local Spring Festival, a vibrant spring celebration taking over Historic Downtown Wading River on Saturday, May 16, 2026, from 10 AM to 5 PM. This walkable, family-friendly event brings together live music, artisan vendors, delicious food trucks, interactive activities, and local businesses for a full day of fun and connection. Guests can explore handcrafted goods, enjoy the beer garden, and take part in activities like face painting, fairy hair tinsel, axe throwing, and more. Rain or shine, Rooted is a celebration of creativity, community, and supporting local in the heart of Wading River.
6. Nesconset Spring Fling, Music Fest and Food Truck Rodeo
When: Sunday, May 17th at 10 AM
Where: Nesconset Gazebo Park, 127 Smithtown Blvd, Nesconset, NY
Head to Nesconset Gazebo Park for an unforgettable community festival packed with fun for all ages! Enjoy delicious eats from some of Long Island’s best food trucks, sip drinks at the beer and cocktail tent, and shop an eclectic mix of curated local vendors. The event also features three live bands, dancing, a mechanical bull ride, bounce houses for kids, face and body painting, tarot readings, permanent and engraved jewelry, sweet treats, snacks, and so much more. Bring your friends and family and soak in all the great community vibes!
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