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Pumpkins, Pies and Picks for Five Fab Fall Festivals

By: Alexa Anderwkavich

Metro Creative

October is here. and that means it’s time to grab your slice of the seasonal spirit here on Long Island! From craft fairs and food festivals to carnival-style fun and everything in between, get out there and find your reason to celebrate with food, crafts and more events for the whole family. 

Montauk Chamber of Commerce’s 41st Annual Fall Family Festival
When: Saturday-Sunday, October 8-9, 2022
Where: Montauk Village Green, 742 Montauk Highway, Montauk

Calling all chowder connoisseur, don’t miss the Annual Chowder Contest on Saturday October 8ths at 11am. Live bands will perform in the Gazebo. Also pumpkin painting, kid crafts, bouncy rides and 30-horse carousel, street painting and delicious treats along with the Chinese Auction, Online Silent Auction and food tent offering delicious treats and Oktoberfest foods. Farmer’s Market Vendors will line the street both days.

Christmas in October Village Craft Fair 2022
When: Saturday October 8, 2022, 10am – 4pm
Where: Smithtown Historical Society, 239 Middle Country Road, Smithtown 

Who says it’s too early for the Christmas season? This craft fair, featuring handmade items by local and tri-state artisans, is the perfect place to shop for gifts for others or treat yourself! There will be one-of-a-kind artwork, photography, handmade jewelry, wonderful home decor, organic body and bath products, wooden crafts, delicious gourmet foods and more.

46th Annual Riverhead County Fair
When: Sunday, October 9
Where: Historic Downtown Riverhead

Agricultural competitions, food, carnival rides and games, local crafts, live music and more turn historic downtown Riverhead into a hotbed of family fun and entertainment.

Long Island Oyster Festival
When: Saturday, October 15-Sunday, October 16
Where: Oyster Bay

Check out one of the East Coast’s largest waterfront celebrations for a shucking good time. Entertain yourself with myriad new activities and old favorites! This weekend-long festival is fun for the whole family and oyster lovers of all ages!

Fall Festival Weekends at The Shoppes at East Wind
When: Weekends through October 30
Where: Wading River

Every weekend in October  The Shoppes at East Wind are featuring local craft vendors, food, and shopping. Enjoy roasted corn, pumpkins, craft vendors, grand carousel, wooden train, The Shoppes Big chair, bounce house East Wind Scarecrow Contest and more.