1. Smithtown Fall Craft Fair
When: Oct 03, 2026 through Oct 04, 2026 (daily)
Where: Smithtown Historical Society, 211 East Main Street, Smithtown, NY
Enjoy a festive fall day at the Smithtown Fall Craft Fair, held on the picturesque grounds of the Smithtown Historical Society at 211 East Main Street. Browse unique handmade crafts and gifts from more than 80 local vendors, visit the farm animals, and enjoy delicious food and live music. Best of all, admission is free!
2. Moonlight Market: Long Island
When: Saturday, October 3rd at 4 PM
Where: Long Island Sports Hub, 165 Eileen Way, Syosset, NY
Get ready to kick off the spooky season at Moonlight Market, New York’s favorite 18+ festival for crafts, curiosities, and oddities! Explore over 150 unique vendors, enjoy delicious food trucks, and visit the sponsors’ pop-up bar. Your General Admission ticket also includes an exciting lineup of live bands, burlesque, drag and cabaret performances, bellydance showcases, workshops, and more. Come celebrate Halloween season with a night of creativity, entertainment, and wonderfully weird finds!
3. Stony Brook Symphony Orchestra
When: Saturday, October 3rd at 7:30 PM
Where: Staller Center for the Arts, 100 Nicolls Rd, Stony Brook, NY
The Stony Brook Symphony Orchestra brings together outstanding musicians from around the world who are pursuing advanced studies in the graduate program of the Department of Music. Under the guidance of renowned performance faculty, the orchestra delivers inspiring performances that showcase exceptional musicianship and artistic excellence.
4. Uncle Giuseppe's 25th Anniversary Food Truck Tour – Smithtown
When: Oct 02, 2026 through Oct 04, 2026 (daily)
Where: Uncle Giuseppe's Marketplace, 95 NY-111, Smithtown, NY
Celebrate Uncle Giuseppe’s Marketplace’s 25th anniversary and kick off Italian Heritage Month with its brand-new food truck! The five-weekend tour begins in Smithtown from October 2–4, serving up fresh, hot sausage and pepper heroes. Come enjoy delicious Italian flavors and join the anniversary celebration!
5. Fall Foliage Adventure Trains
When: Catskill Mountain Railroad Co, 55 Plaza Rd, Kingston, NY
Where: Every Friday, Saturday and Sunday through October 11
Experience the beauty of autumn on the Catskill Mountain Railroad’s Fall Foliage Adventure Train Ride this September and October 2026. Enjoy a scenic journey through the Catskills, traveling along the historic former Ulster & Delaware Railroad corridor. Along the way, take in vibrant fall colors, historic farmlands, the Esopus Creek, the restored C9 Bridge, Hurley Flats, and the foothills of Hurley Mountain. Fun for both adults and children, this is a wonderful way to experience the spectacular beauty of the season from a unique perspective.
6. Long Island Family Day – Cradle of Aviation
When: Sunday, October 4th at 12 PM
Where: Cradle of Aviation Museum, Charles Lindbergh Boulevard, Garden City, NY
Get ready for an unforgettable day of family fun at Long Island Family Day! Enjoy interactive games, exciting raffles, giveaways, dance classes, face painting, balloon twisting, a photo booth, a video game tournament, music, and more. Families can also explore local schools, after-school programs, educational resources, STEM/STEAM activities, and special needs resources. Whether you’re a parent, grandparent, or simply looking for a fun day out with the kids, there’s something for everyone to enjoy!
7. Comedy Night at the Seaport Diner
When: Sunday, October 4th at 6 PM
Where: Seaport Diner, 5045 Nesconset Hwy, Pt. Jefferson Station, NY
Join us for a fun-filled evening featuring a delicious 3-course dinner followed by a stand-up comedy show with comedians Jen Snorteland, Jeff Goldberg, and Eric Tartaglione! Dinner begins at 6:00 PM, with the comedy show starting at 7:15 PM. Tickets are $45 per person, including coffee, tea, and soda, plus tax and tip. Enjoy $6 beer and wine and $10 mixed house drinks throughout the evening. Come hungry and ready to laugh!
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