1. Smithtown Historical Heritage Country Fair
When: Saturday, September 19th at 12 PM
Where: Smithtown Historical Society, 239 Main St, Smithtown, NY
Join us for a special Heritage Country Fair on the historic farm as we celebrate its 250th anniversary! Step back in time with antique cars, historical reenactors, traditional weaving and spinning, live music, delicious food, local crafters, and farm animals. Enjoy the petting zoo, hands-on crafts, and plenty of family-friendly activities throughout the day. FREE EVENT! Come celebrate history, heritage, and community with us!
2. The Fall Farm Festival
When: September 19 - 20, 2026
Where: White Post Farms, 250 Old Country Road, Melville, NY
White Post Farms Fall Farm Festival is celebrating its 36th year as Long Island’s original Fall Farm Festival! Enjoy pumpkin picking, family photo opportunities, a scenic hayride through the cornfields, and six exciting live performances featuring amazing pigs, stunt dogs, magic, dancing, acrobatics, and more. Indulge in delicious fall favorites like roasted corn and cider donuts, pick up an award-winning apple pie, and visit the Animal Farm—all included with festival admission. Save $10 per ticket through October 4 with code FALL10 when booking online!
3. Glen Cove Street Fair
When: Saturday, September 19th at 10 AM
Where: Glen Cove Street Fair, 1 Glen Street, Glen Cove, NY
Join us at the Glen Cove Street Fair on September 19th at 10:00 AM! Come enjoy a fun-filled day with local vendors, great food, shopping, and community entertainment. We’d love to see you there!
4. Babylon Pumpkin Fest
When: Sunday, September 20th at 11 AM
Where: Salt Shack Cedar Beach, 100 Ocean Parkway, Babylon, NY
Join us for the Babylon Pumpkin Fest at Salt Shack Cedar Beach on September 20th! Enjoy a fun-filled day featuring festive activities, pumpkins, beachside vibes, and family-friendly entertainment. Bring your friends and family and celebrate the start of the fall season by the shore!
5. Fall Festival at Hicks Nurseries
When: Hicks Nurseries, 100 Jericho Turnpike, Westbury, NY
Where: Sep 17, 2026 through Nov 01, 2026 (daily)
Celebrate the beauty of fall at the 51st Annual Hicks Nurseries Fall Festival in Nassau County! This beloved Long Island tradition brings families together for a day filled with Halloween fun, seasonal shopping, fall favorites, and festive activities. Explore the NEW Fall Festival Market and Skeleton Estate Garden, meet Otto the Ghost, enjoy an animated Halloween walkthrough, play lawn games, listen to live music on select Sundays, and wander through thousands of pumpkins, mums, and colorful fall displays. Best of all, admission is free!
6. HarborFest
When: September 19 - 20
Where: Marine Park, Marine Park Dr, Sag Harbor, NY
HarborFest 2026 is back for a fun-filled weekend celebrating the village’s rich maritime history! Head to Long Wharf for live music, kids’ activities, delicious food, beer and wine, and dozens of local vendors—including SASF and their adorable adoptable dogs. Bring the whole family and enjoy a weekend of community, entertainment, and waterfront fun!
7. The Long Island Wine & Food Classic
When: September 19th at 7 PM
Where: Farmingdale State College, 2350 New York 110, Farmingdale, NY
Join us for the Long Island Wine & Food Classic on Saturday, September 19, 2026, at Farmingdale State College! Led by Chef Eric LeVine and hosted by DJ CHEF, this all-inclusive tasting experience will bring together 25+ restaurants and 20+ beverage companies, along with talented chefs, specialty food purveyors, vineyards, craft breweries, and premium beverage brands for an unforgettable celebration of Long Island’s food and drink scene.
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