1. White Post Fall Farm Festival
When: September 20 - 21
Where: White Post Farms, 250 Old Country Road, Melville, NY
The White Post Farms Fall Farm Festival has been a Long Island tradition for over 30 years, and it’s back again this September! As Long Island’s original Fall Farm Festival, it’s the perfect family outing filled with seasonal fun. Enjoy pumpkin picking in the massive pumpkin field, hop on a hayride through the cornfields, and capture plenty of family photo ops along the way. This year’s festival features six exciting live performances, including the famous Pork Chop Revue from America’s Got Talent, the interactive Barnyard Bash Dance Party, two incredible dog shows—Dominguez Attractions and Mutts Gone Nuts—plus Rodeo Ricky’s Country Jamboree and a brand-new magic show sure to amaze kids of all ages. And of course, no festival is complete without delicious fall treats like roasted corn, cider apple donuts, and freshly baked award-winning apple pies to take home. Don’t miss out—use code FALLFESTIVAL2025 to save $10 on online tickets for September 20, 21, 27 & 28 only!
2. Long Island Family Day 2025
When: Sunday, September 21st 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 — the ultimate Back-to-School celebration! This lively event brings families together to explore exciting resources while enjoying interactive games, raffles, giveaways, and hands-on activities for all ages. From bounce houses, face painting, photo booths, and arts & crafts to educational showcases featuring schools, after-school programs, STEM/STEAM activities, and special needs resources, there’s something for everyone. Whether you’re a parent, grandparent, or simply looking for a fun-filled day out with the kids, Long Island Family Day promises laughter, learning, and lasting memories.
3. The “725 Art Show” at the Sag Harbor Whaling and Historical Museum
When: September 20 - 21
Where: Sag Harbor Whaling & Historical Museum, 200 Main Street, Sag Harbor, NY
The Sag Harbor Whaling and Historical Museum is excited to close the season with the return of the beloved 725 Art Show, a tradition celebrating the creativity of our local community. Originally conceived by the late Elinor and Bob McDade and named after the original Sag Harbor telephone exchange, the show was once held at the Goat Alley Gallery before moving to the Museum in 2018. This year’s exhibition once again showcases an inspiring collection of paintings, sculpture, drawings, and photography by resident artists—all available for purchase, offering the perfect chance to bring a unique piece of Sag Harbor into your home. We are especially delighted to welcome back Michael A. Butler, former Museum staff member, as guest curator for this year’s show.
4. Long Island History Hunt
When: Sep 18, 2025 through Sep 30, 2025 (daily)
Where: Long Island History Hunt, Long Island, NY
This summer, Long Island museums and historical societies from Brooklyn to Montauk are coming together to present the Long Island History Hunt—a FREE adventure where history comes alive at a dozen iconic sites. From uncovering the secrets of the Culper Spy Ring to exploring the legacy of Theodore Roosevelt, visitors can experience the stories of spies, patriots, and presidents who helped shape our nation. Running from July 1st through September 30th, participants can register at LI History Hunt and take on fun selfie challenges at historic homes, museums, landmarks, parks, and even a colonial tavern. Each completed challenge enters visitors for prizes, while those who complete all 12 earn the title of Revolutionary Trailblazer and a chance at the grand prize—$500, a historic 18th century-style luncheon, family museum memberships, and more. Along the way, participants can also enjoy nearby New York State Parks for picnics and relaxation, making it a perfect mix of history, fun, and adventure.
5. Bayville Scream Park
When: September 20 - 21
Where: Bayille Scream Park, 8 Bayville Ave, Bayville, NY 11709, Bayville, NY
This year marks the 20th anniversary of Long Island’s most infamous fright zone, and it’s bigger, scarier, and more thrilling than ever. Experience five newly re-imagined haunted houses, from the pitch-black halls of Uncle Needle’s Funhouse of Fear to the cursed tunnels of the Temple of Terror—all included with one scream-filled ticket. Between scares, sneak away to one of three hidden 21+ bars, challenge your friends to GellyBall battles, or take on axe throwing, mini golf, and arcade mayhem along the midway. With over 1,860 five-star reviews and the title of “Scariest Haunted Houses on Long Island,” this fear-for-all carnival of chaos is not to be missed.
6. Long Island Cares 4th Annual 5k & Paws Walk
When: Sunday, September 21st at 8 AM
Where: Belmont Lake State Park, 625 Belmont Ave, West Babylon, NY
Get ready to lace up your sneakers and leash up your furry friends—Long Island Cares’ 4th Annual 5K & Paws Walk is returning to the scenic Belmont Lake State Park! This pet-friendly charity event is perfect for everyone, whether you’re a runner aiming for a personal best, a casual walker taking in the beautiful surroundings, or simply there to soak up the wag-tastic vibes with fellow animal lovers.