Best Fall Fairs and Festivals for Long Island Families

Favorite Festivals, Fairs, and Feasts for LI Families Fall 2017

The leaves soon will turn and the smell of apple cider donuts and roasted corn will be in the air. Soon, you’ll have to put on an extra layer to keep warm, but no one really mind if it means enjoying a seasonal treat and spending some family time outside. It’s fall fairs and festivals season, and we’ve pulled together a list of some of the best this September and October, including a peek into Halloween fun. So grab a sweater and enjoy this in-between season before the real chill sets in.

 No matter where you live—Nassau, Suffolk, or the East End—fall on Long Island is beautiful, and there’s plenty of family fun to be had. Check out our fall fun guide for more ideas.

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Enjoy the pageantry of the Shinnecock people on Labor Day weekend. 

Annual Shinnecock Indian Powwow — Southampton
August 31- September 3
One of the largest Native American gatherings on the East Coast, the Shinnecock Indian Powwow has welcomed guests for more than 70 years. Enjoy daily dance competitions, entertainers, Native American arts and crafts, and cultural enrichment opportunities for adults and children. 

Brookhaven Country Fair — Ridge
September 8-9
The Longwood Estate hosts this two-day event with craft vendors, food, historic re-enactments, children’s activities, live music, a train show, and more. Leashed pets are welcome.

Harbes Orchard Apple Festival — Mattituck
September 8-9
Think you have what it takes to win an apple cider donut eating competition? Competitors try their best at this two-day apple festival that also includes an apple rolling competition, wine tastings, hayrides, pony rides, live music, vendors, and additional children’s activities. FREE to attend, but apple picking and the corn maze require paid admission.

RELATED: Where to pick your own apples on LI


Take a trip back to the East End's agricultural past at the Hallockville Fall Festival.

Hallockville Fall Festival and Craft Show — Riverhead
August 25-26
Join in on this old-fashioned country fair that is a North Fork tradition. Celebrating Hallockville’s agricultural traditions and rich folk art, the fair includes craft demonstrations, a vendor fair, tractor pull, live music, children’s activities and games, museum tours, and farm animals.

Colonial Day at Raynham Hall Museum — Oyster Bay
September 9
Relive history at this event filled with costumed Colonial adult and child re-enactors. The 18th century comes to life with music, colonial cooking demonstrations, and even musket firings. This event also features a militia group that camps on the grounds of the museum, engaging visitors with tales about life and war during that time in history. FREE

North Hempstead KidStock — Port Washington
September 15
This annual festival at North Hempstead Beach Park is all about kids and music. Featuring a variety of musical groups and entertainers as well as kids’ activities and games, this festival is sure to get kids dancing and singing. FREE, but parking is $10.


Enjoy traditional lion dances at Port Jefferson's Annual Dragon Boat Race Festival.

Port Jefferson’s Annual Dragon Boat Race Festival – Port Jefferson
September 15
Cheer on the dragon boat racing teams and get a chance to see the boats up close. This festival features Asian performing arts, cultural and educational vendors, and lots of food, including sushi, spring rolls, bubble tea, and pot stickers. FREE

Fall Festival at Hicks Nurseries — Westbury
September 15 - October 28
Visit "Otto the Ghost" and take a hayride at Hicks Nursery’s annual fall event. Otto tells a story of friendship, family, and Halloween cheer, and kids can get their photos taken with Otto afterward. There will be farm animals, plenty of apples, pumpkins, and other tasty treats. FREE

RELATED: 100 things to do with LI kids before they grow up 


Cheer on the Junior Iron Chefs at the Garlic Festival in Aquebogue. 

Long Island Garlic Festival — Aquebogue
September 15-16
This one is for the garlic lovers. Celebrate this small, pungent bulb by learning about farming and enjoying food made using garlic. Enjoy crafts, live music, a garlic-eating contest, and a Junior Iron Chef Garlic competition. 

Italian Experience Festival — Hempstead
September 16
Hofstra University presents the "Italian Experience" at its South Campus. This outdoor festival celebrates Italy’s culture, traditions, and commerce in America. Family-friendly activities include music, dance, a bounce house, puppet show, face painting, and a magic show. There will be plenty of Italian food, crafts, and community booths. 

Pal-O-Mine’s Fall Festival and Open House — Islandia
September 23
Pal-O-Mine Equestrian opens its doors for a day of family fun. WALK 97.5 radio broadcasts live and there is face painting, musical saddles, a photo booth, and vendors. Pal-O-Mine horses put on interactive demonstrations, and the first 30 children receive a back-to-school gift. FREE

Egyptian Festival — Woodbury
September 21-23 and 28-30
This cultural festival features a ride on tour through “Old Egypt,” where riders experience different areas of the country. Taste authentic Egyptian dishes, take a photo in the Egyptian-themed photo booth, learn through cultural displays, and shop the Egyptian bazaar. Kids can enjoy the bouncers, bubble mania, and other games. St. Joseph’s Hospital will even be on hand for anyone interested in getting a flu vaccine. FREE

Wildwood Fall Festival — Wading River
September 22
Wildwood State Park hosts this annual event that features craft vendors, entertainment, a petting zoo, pony rides, moon bounce, refreshments, and more. This event draws a large crowd and offers something fun for seemingly everyone. FREE

RELATED: Classes and after-school programs for LI kids


Celebrate the seaport's aquatic heritage at the Greenport Maritime Festival.

Greenport Maritime Festival — Greenport
September 21-23
Greenport closes some of its streets to traffic for this weekend event. The festival kicks off with an opening-day parade down Main Street. The marina will be filled with hand-crafted wooden boats and a display of iceboats will also be available. There will be a children’s story time and live demonstrations. FREE

Seaford Harvest Fair — Seaford
September 23
Support the Seaford Historical Society and have some fun. The fair takes place on Waverly Avenue and in the Seaford Historical Museum parking lot. There will be more than 50 vendors, entertainment, food, raffles, and kids’ activities. FREE

Caleb Smith Fall Festival – Smithtown
September 30
Learn about nature and the historic past of Caleb Smith State Park and Preserve. Kids can fish with FREE bait and tackle, and pumpkins are FREE for kids 12 and younger. Naturalists will be on hand to give tours, and there will be live music, face painting, and Colonial crafts and games. Adults and kids will enjoy the classic cars. FREE

Fall Festival at Sagtikos Manor — West Bay Shore
October 7
Live music and historical and crafting demonstrations will be part of this festival. The 3rd NY Regiment will be present, performing maneuvers and demonstrating daily life routines. Craft demonstrations include: spinning, weavers, cooking, broom making, beekeeping, pottery making, rug hooking, quilting, leather working and metal smithing. Children’s activities include arts and crafts and old fashioned games and listen to Colonial Musicians.

Plainview-Old Bethpage Fall Festival – Plainview
September 30
This year’s event is at the Plainview-Old Bethpage public library parking lot and is expected to draw a large crowd. There will be craft vendors, live music, plenty of food options, and activities for kids. FREE


Take a walk through the haunted woods at Spooky Fest.

Spooky Fest — Rockville Centre
October 13, 19, 20, 21, 26, 27, 28
Enjoy seven days of Halloween fun for the whole family at the Center for Science Teaching and Learning. Scary attractions include haunted woods and a maze of zombies; non-scary attractions include a fun walk in the woods, friendly Merry Monsters, kids’ arts and crafts area, Halloween theater, amazing animals, and more.

Harvest Fair — Southampton
October 13
Celebrate life during the 19th century at the Southampton Historical Museum. See how adults and children worked to create a sustainable home life, and take a peek at the consignment shop. There is a bake sale and museum admission is $4.

Fall Family Freshwater Fishing Festival — West Hempstead
October 20
Hempstead Lake State Park hosts this family event, which incorporates fishing activities with a fall theme. Kids cast for pumpkins, decorate pumpkins, and enjoy fly fishing demonstrations. No need to bring equipment; rods are available for loan on a first-come, first-served basis.There is also be face painting and craft activities.

Islip Fall Festival — Islip
October 27
The Islip Chamber of Commerce’s first annual fall festival includes live entertainment, line dancing, a pumpkin patch, kids’ costume parade, face painting, and craft vendors. For those with big appetites, there is a charity pie eating contest and plenty of food vendors.

Halloween Family Fun Fest — Rockville Centre
October 27
Put on your costume and head to the Madison Theatre at Molloy College for a day of spooky fun. Admission includes pumpkin picking and decorating, a haunted house, cupcake decorating, Duck Pluck game, balloon creations, food trucks, entertainment, and a costume contest.

Great Jack-O-Lantern Spectacular Sail — North Babylon
October 28
At this family event at Belmont Lake State Park, the first 50 carved pumpkins brought by attendees are placed on flotation devices and lit with candles and then sailed by kayaks around Belmont Lake at dusk. Earlier in the day there are environmental crafts, funny photos, a children’s spooky den, trick or treating, and balloon twisting. FREE

Oktoberfest — Riverhead
October 27-28
Sit back and enjoy live Bluegrass music in a farm setting. Garden of Eve Organic Farm hosts this annual event that features craft beer for adults and the Family Fun Fields for kids. The fields include a pedal kart track, maze, lovely lavender labyrinth, and farm animals. Pick up a pumpkin and fall mums and enjoy food from the farm’s cafe. FREE

Ragamuffin Parade — Sag Harbor
October 28
Kids, adults, and even pets can show off their costumes during this parade down Main Street in Sag Harbor. The parade ends at the Custom House Lawn, where games and a bake sale are planned.

This article was originally published in 2016. It was updated in August 2018.

Top photo: Jack-o-lanterns are set afloat on Belmont Lake during the Great Jack-o-Lantern Spectacular Sail. Photo courtesy of Long Island State Parks and Recreation. Unless noted, photos courtesy of the organizers/festivals.

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