September is one of the best months to explore Long Island. The final days of summer begin giving way to apple picking, pumpkin patches, village fairs, outdoor markets and the first true signs of fall.
Whether you’re looking for a family-friendly farm experience, a waterfront festival or an excuse to explore a new Long Island community, these September 2026 events deserve a place on your calendar.
September Events in Nassau County
Nature Connects at Old Westbury Gardens
Through September 7 | Old Westbury
Explore Old Westbury Gardens while viewing 17 nature-inspired sculptures made from more than 300,000 LEGO bricks. This is the final week to see the exhibition before it closes for the season.
Bellmore Family Street Festival
September 17–20 | Bellmore
The annual Bellmore Family Street Festival returns with carnival rides, live music, food, vendors, crafts and entertainment throughout Bellmore Village. The carnival opens on Thursday, while the main street festival takes place Saturday and Sunday.
Glen Cove Street Fair
September 19 | Glen Cove
Downtown Glen Cove will be filled with food, local vendors, live music and family-friendly activities during this free community street fair.
The Fall Finale
September 20 | Point Lookout
Celebrate the transition into fall at Town Park Point Lookout with a waterfront car show and seasonal community festivities.
The Long Island Fair
September 25–27 | Old Bethpage
The Long Island Fair returns to Old Bethpage Village Restoration for a weekend celebrating Long Island’s agricultural history. Visitors can enjoy farm animals, historic demonstrations, live entertainment, games, craft vendors and traditional fair food.
Great Marques Concours d’Elegance
September 27 | Glen Cove
Morgan Memorial Park provides the waterfront setting for a display of distinctive collector and luxury automobiles. It’s an especially picturesque outing for car enthusiasts and anyone looking for something different to do on a September Sunday.
Glen Cove Fall Family Festival
September 27 | Glen Cove
The Glen Cove Fall Family Festival offers another opportunity to enjoy seasonal activities and community fun on the North Shore.
Pumpkin Painting at Old Westbury Gardens
September 30 | Old Westbury
Close out September with a creative seasonal activity at one of Nassau County’s most beautiful historic properties.
September Events in Suffolk County
Greenlawn Fireman’s Fair
September 3–6 | Greenlawn
Kick off Labor Day weekend with rides, food, games and traditional fair festivities hosted by the Greenlawn Fire Department.
Harbes Honeycrisp Apple Festival
September 5–6 | Jamesport
Celebrate the beginning of apple season with Honeycrisp apple picking, live music, farm food, local vendors and family activities at Harbes Farms Jamesport.
Korea Festa
September 5–7 | Huntington
Korea Festa brings food, entertainment, cultural experiences and family activities to Huntington over Labor Day weekend.
Hank’s Pumpkintown Opening Weekend
Beginning September 12 | Water Mill
Hank’s Pumpkintown opens for its 2026 season with apple and pumpkin picking, corn mazes, wagon rides, games, playgrounds and plenty of cider doughnuts and seasonal treats.
Long Island Garlic Festival
September 12–13 | Riverhead
Waterdrinker North Fork hosts the 24th Annual Long Island Garlic Festival with live music, a vendor market, food trucks, family activities, a corn maze, hayrides and plenty of garlic-inspired food.
Civil War Weekend at the Grange
September 12–13 | Sayville
Step into Long Island history during the 18th Annual Civil War Weekend at the historic Grange in Sayville.
F&W Schmitt’s Family Farm Fall Festival
Beginning in September | Melville
F&W Schmitt’s annual fall season includes pumpkin picking, a seven-acre corn maze, wagon rides, a petting zoo, playground activities and seasonal photo opportunities.
Waterdrinker Fall Festival
Beginning September 21 | Manorville
Waterdrinker’s classic fall experience includes pumpkin picking, a corn maze, weekend hayrides, barnyard animals, games and seasonal photo opportunities.
Greek Fest
September 18–20 | Greenlawn
St. Paraskevi Greek Orthodox Shrine Church hosts a weekend of Greek food, music, dancing, vendors and rides.
Greenlawn-Centerport Pickle Festival
September 19 | Greenlawn
The annual Pickle Festival returns to John Gardiner Farm with pickles, local history, vendors and family-friendly entertainment.
Port Jefferson Dragon Boat Race Festival
September 19 | Port Jefferson
Colorful dragon boats take over Port Jefferson Harbor during this distinctive waterfront festival at Jeanne Garant Harborfront Park.
Harbes Sunflower Festival
September 19–20 | Jamesport
Spend the weekend walking through sunflower fields while enjoying apple picking, pumpkin picking, hayrides, live music, local vendors and seasonal food at Harbes Farms Jamesport.
Cow Harbor Day
September 20 | Northport
One of Northport’s most beloved traditions returns with a Main Street parade, music, vendors, rides, decorated boats and the annual crazy boat race at Northport Village Harbor.
LIMEHOF Music Documentary Film Festival
September 25–27 | Stony Brook
The Long Island Music and Entertainment Hall of Fame will present more than 40 feature-length and short music documentaries, with select screenings accompanied by filmmaker conversations and live performances.
Wading River–Shoreham Fall Festival
September 27 | Wading River
The Shoppes at East Wind hosts a seasonal community festival celebrating the arrival of fall in Wading River.
Make the Most of September on Long Island
September offers the perfect combination of lingering summer weather and early fall atmosphere. You can spend one weekend near the water and the next wandering through an apple orchard, pumpkin patch or historic village.
Event dates, hours, admission policies and weather-related plans may change. Before attending, verify the latest information directly with the event organizer.
Exploring Long Island’s villages is also one of the best ways to discover what makes each community feel like home. If you’re considering buying or selling in Nassau or Suffolk County, I’d be happy to help you understand the local real-estate market and find the community that best fits your next chapter
