Kids eager for an extended vacation might not agree, but is there a finer month on Long Island than September? As summer winds down and the weather cools, the region begins its colorful transition into autumn’s pageantry.
September weekends offer seasonal and cultural celebrations and a chance to discover Long Island’s natural beauty. Immerse yourself this month in Native American culture and traditions, explore maritime history, or spend a day on the East End visiting a farm. Or maybe just explore a museum, lighthouse, or seasonal festival.
Whatever you choose, your family is bound to have fun, learn something, and make memories. Here then is our list of the best ways to keep your family entertained in this back-to-school month.
Remember, our Long Island Events Calendar is updated regularly, so check often for the latest in fun, family-friendly events. Don't miss our Fall Family Fun Guide, and for the most up-to-date news sign up for our FREE newsletters.
Native American culture comes alive at the annual Shinnecock Indian Powwow. Photo courtesy of the tribe
Shinnecock Indian Powwow — Southampton
Friday, August 30-Monday, September 2
Discover the rich history of Long Island’s indigenous people as the Shinnecock Nation welcomes all to its annual powwow, one of the largest Native American gatherings on the East Coast. Thrill to competitive and ceremonial dances, prayers, music, arts and crafts, food, and more. Don’t miss the grand entry at 7pm on Friday, Saturday, and Sunday, climaxed each night by the sunset fire lighting.
Hampton Classic Horse Show — Bridgehampton
Friday, August 30-Sunday, September 1
This world-class equestrian competition concludes on the Sunday of Labor Day weekend with the Grand Prix. Horse lovers from all across Long Island will thrill to competition in hunter and jumper disciplines and in youth and adult divisions. Kids will enjoy special activities in the kids tent, including a family circus, DJs, face painting, pony rides, and more.
Longwood Fair — Oyster Bay
Saturday, September 7-Sunday, September 8
Enjoy historical re-enactments, children’s activities, music, pet shows, and more at the first of Long Island’s fall festivals. Tours of Tesla Science Center pay tribute to the electrical engineer and designer of the alternating current (AC) electricity supply system.
Colonial Day at Raynham Hall — Oyster Bay
Sunday, September 8
Raynham Hall comes alive with costumed re-enactors from the Colonial period. Kids can enjoy a return to 18th-century life with period music, cooking demonstrations, musket firings, and more. The Huntington militia, founded in 1653, camps on the grounds of the museum and immerses guests with tales of the Founding Fathers. FREE
Radio-Controlled Aero Show — Oyster Bay
Sunday, September 8
Have a budding aviator in the family? This radio-controlled model airplane show at Sunken Meadow State Park promises great fun for all, and all demonstrations are FREE.
Long Island Live Steamers — Oyster Bay
Sundays, September 8 and 22
Train enthusiasts young and old will thrill to Long Island Live Steamers’ twice-monthly public run days. Visitors can ride steam, diesel, and electric trains on eight acres of scale tracks ideal for young children. Public run days at Brookhaven County Park continue through mid-October so this is one of your last opportunities to enjoy this uniquely Long Island activity.
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Kids will thrill to the annual Dragon Boat Race in Port Jefferson. Enjoy an Asian celebration, too. Photo courtesy of Port Jefferson Chamber of Commerce
Dragon Boat Race Festival — Port Jefferson
Saturday, September 14
Watch as teams of dragon boats compete across a 250-meter course in vessels similar to outrigger canoes. The festival also includes performing arts, Asian cultural activities, food, vendors, and more. FREE
Long Island Garlic Festival — Riverhead
Saturday, September 14-Sunday, September 15
If your family appreciates a little garlic in your entrees, you won’t want to miss Long Island’s only celebration of the spicy vegetable. (Yes, garlic is most accurately described as a vegetable). Enjoy garlic-inspired food, crafts, music, hayrides, a bounce house, farm animal area, and more at Garden of Eve Organic Farm.
Harbes Orchard Apple Festival — Riverhead
Saturday, September 14-Sunday, September 15
Enjoy apple-themed activities all weekend long at this 15-acre farm on the East End, including apple cider doughnut-eating contests, apple rolling competitions, and more. Pick apples from branches within easy reach of little hands. Kids can also challenge themselves in the Robin Hood-themed corn maze while parents can enjoy a glass of wine from Harbes Vineyard.
Italian Experience at Hofstra University — Hempstead
Sunday, September 15
Hofstra’s Italian Experience celebrates Italy's gifts of culture, education, and commerce to America. Enjoy food, vendors, handmade crafts, cultural exhibits, music, dance, poetry, and more. Expect a crowd.
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Beware of the "pirates" in Greenport during the Maritime Festival. Photo courtesy of the Village of Greenport
Greenport Maritime Festival — Greenport
Saturday, September 21-Sunday, September 22
A parade down Main Street in Greenport Village kicks of this weekend-long event that features boat displays, water sports, kayak races, model ship building, fishing, food, crafts, and more. There are plenty of kid-friendly events, including a coffee sack race, Irish step dancing, and even a children’s breakfast on Sunday morning, where you just might spot some mermaids and pirates. FREE admission.
Egyptian Festival — Woodbury
Friday, September 20-Sunday, September 22; Friday, September 27-Sunday, September 29
This festival, at St. Mark's Coptic Church, celebrates Egyptian food, culture, traditions, and more. Kids can enjoy bouncers, bubble mania, and other games while adults can sample authentic Egyptian dishes, take a photo in the Egyptian-themed photo booth, and shop in the Egyptian bazaar.
DogFest Long Island 2019 — Deer Park
Saturday, September 21
Grab your furry friend and his or her leash and get ready for a day of dog demonstrations, canine agility courses, music, food, and more to benefit Canine Companions for Independence, whose assistance dogs help children and adults with disabilities. FREE with raffles to support the organization.
Long Island Fair — Deer Park
Saturday, September 21-Sunday, September 22; Saturday, September 28-Sunday, September 29
Step back to the past at Old Bethpage Village Restoration for an old-time county fair. Enjoy lumberjack shows, Wild West and magic performances, a petting zoo, camel rides, and more at grounds designed to re-create the famous Mineola Fairgrounds of the 19th and early 20th centuries.