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12 Long Island Festivals to Fall Into Right Now

By: Alexa Anderwkavich
09/17/2022
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Metro Creative

Gather your mums (and dads and kids and friends, while you’re it) for a bounty of Long Island fall festivals happening over the next few weeks of September. From pumpkins spice everything to corn mazes, fall festivities are back in full swing and it’s time for family-fun. Check out these local activities and start marking your calendars—there’s so much to do this autumn on our Long Island home! 

Pickle Festival
Where: John Gardiner Farm 900 Park Avenue, Huntington, NY
Sept. 17
10 a.m. to 4 p.m.

Calling all pickle lovers to John Gardiner Farm for the 42nd Annual Pickle Festival presented by the Greenlawn-Centerport Historical Association. Enjoy fried pickles or pickles on a stick, but save some space for roasted corn or fresh farm stand produce. Take a ride on the Lollipop Farm Train or hop on for a hayride, try to navigate the corn maze or peruse some antique cars or the pickle history display.

Draw Out! Free Community Arts Festival at Heckscher Museum of Art
Where: 2 Prime Avenue Huntington
Sept. 17
Noon to 5 p.m.

Unleash your inner artist with a day full of art, music and creativity within the art museum at Heckscher Park. Soothe your soul with watercolors by the pond or sketch a live model, listen to live music on the terrace while creating alongside guest artists. There will also be a dance performance inspired by the exhibition. 

Long Island Fair
Where: Old Bethpage Village Restoration 1303 Round Swamp Road, Old Bethpage, NY
Sept. 17 and 18
10 a.m. to 5 p.m.

The Long Island Fair allows you to step back into the olden days, with blue-ribbon competitions in horticulture, needlework and agricultural skills, to name just a few of the classic events. The fair also includes thousands of exhibits. Entertainment includes Wild West shows, butterfly encounter experiences, puppet and magic shows, and, of course, tons of carnival cuisine to enjoy!

41st Annual Country Fair & Craft Show Presented By: Hallockville Museum Farm
Where: Hallockville Museum Farm, 6038 Sound Ave, Riverhead
Sept. 17 and 18
10 a.m. to 5 p.m.

This 28-acre preserved farm homestead known as Hallockville Museum Farm on the North Fork will host its 41s Country Fair and Craft Show and celebrate “old-school” by unplugging and relishing in an authentic country fair experience. Take a wagon or pony ride, join a food competition, roam the farmers market for local fresh produce, take in the scents of homemade baked goods, and so much more. Folk art demonstrations will take place, and handcrafted wares are also for sale. There will be plenty of good food and drinks, great company and live music!

Fall Harvest and Otto the Ghost at Hicks Nurseries
Where: Hicks Nurseries, 100 Jericho Turnpike, Westbury
Sept. 17  to Oct. 30
10 a.m. to close

Come one, come at all at Fall Harvest at Hicks Nurseries, where kids revel in festival fun, like hay mazes and crafts, and adults can stock up on fall decor and much more. Visit Otto the Ghost on a walk-through adventure called “Otto’s Sweet Journey,” which follows the tale of Otto as he travels the world searching for sweet treats to share with his pals. Socially distanced photo-ops with Otto start September 17th. Games for children, tasty fall food, farm animals and pumpkin contests will also ensue! Admission is free, but Hicks is welcoming canned food donations.

Syosset Street Fair
Where:  Syosset LIRR Station, Jackson Avenue (just north of the tracks), Syosset
Sept. 18
10 a.m. to 5 p.m.

It’s been a while, but the Syosset Street Fair, hosted by the Syosset-Woodbury Chamber of Commerce is back! This family-fun fair includes pony rides, petting zoo, bouncy house and other exciting activities for kids. The ShowMobile will host live performances all day, and there are myriad food trucks to try! There will be more than 100 vendors, from artists to many local businesses. Free swag bags and raffle baskets will be given out throughout the day.

Bellmore Family Street Festival
Where: Bellmore LIRR Station, Sunrise Highway & Bedford Avenue
Sept. 22 to 25
Carnival: Sat. 11 a.m. to 11 p.m. and Sun. 11 a.m. to 10 p.m.
Street Fair: Sat. 11 a.m. to 6 p.m. and Sun. 11 a.m to 6 p.m.

The Bellmore Street Festival is fun for everyone, whether you’re looking for carnival or a street fair, this event offers the best of both worlds! Various ventures include crafts, home improvement ideas, and sports and kids expos. Indulge in carnival rides, games and food, or explore business booths, radio booths and more. Free shows for kids include music, animals and magic!

8th Annual Oktoberfest Celebration Benefit
Where: Camp Pa-Qua-Tuck, 2 Chet Swezey Rd., Center Moriches
Sept. 23: 6 p.m. to 11 p.m.
Sept. 24: noon to 11 p.m.
Sept. 25: noon to 6 p.m.

The Rotary Club of the Moriches hosts an ode to Bavarian culture at Camp Pa-Qua-Tuck, with all proceeds benefiting Camp Pa-Qua-Tuck. There will be traditional German food and Oktoberfest Beer Gardens and carnival fun. Enjoy brats and rides, beer and live entertainment, all while giving back. Entry includes a complimentary beer or soda. This festival will take place rain or shine. 

Wildwood Fall Festival
Where: Wildwood State Park (Long Island), 790 Landing Rd., Wading River
Sept. 24
11 a.m.  4 p.m.

The annual Fall Festival at Wildwood is a fun-filled day great for families. Featuring a plethora of activities from craft vendors to live entertainment to plenty of refreshments to quench your thirst. Children’s activities include games, wagon and pony rides, petting zoo and a pumpkin weight raffle.

Grace Church 17th Annual Harvest Fair
Where: 23 Cedar Shore Drive, Massapequa
Sept. 24
10 a.m. to 4 p.m.

Celebrate the 17th Annual Harvest Fair with fresh produce, baked goods and plenty of activities. The farmers market will have L.I.-grown vegetables, cornstalks and pumpkins, hay bales and mums. Try artisanal homemade goods like relishes, jams and jellies, baked goods or good old comfort food. There will be live music and crafts tables, with woodworking, handmade gifts and crafts, and stitchery. Test your luck with a massive gift basket auction or lottery tree. For the kids there’s pumpkin decorating, face painting, games, petting zoo and pony rides, among other activities. 

Greenport Annual Maritime Festival
Where: Mitchell Park, 115 Front Street, Greenport (and throughout the village)
Sept. 24 and 25
10 a.m. to 5 p.m.

Celebrate Greenport’s maritime heritage at the Maritime Festival. Saturday morning’s parade kicks off the festival, followed by displays of classic wooden boats, water sports demonstrations, wood carving, model ship building, music, children’s activities, and craft beers and local wines. The sea-inspired fun continues on Sunday.

Long Island Harvest Festival—Apples & Pumpkins & Mums—Oh My!
Where: Tanger Outlets Riverhead, 200 Tanger Mall Drive, Riverhead
Sept. 25
10 a.m. to 5 p.m.

At this unique festival experience, you can sample and purchase fall menu foods from local farms and restaurants from across the island. Talk to classically trained chefs, meet food truck owners, purchase one (or two) of your favorite drinks from one of many breweries, vineyard or cider houses. There is fun and entertainment for kids, teens and adults with yard games, Bubble Palooza Bubble Bash and more interactive activities. This is a great place to meet the amazing creators behind many of your favorite products, from artists and chefs to children’s entertainers and artisan, and support the local Long Island business community.