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Fall Festivals and Fun on Long Island

October 15, 2019

The cooler air and vibrant colors combine to create perfect fall days for family-themed festivals, food and wine events, Halloween fun, cornfield mazes and of course, pumpkin picking.

Below are some of our favorite fall activities to enhance your seasonal plans. Be sure to tag #DiscoverLongIsland when you are out and about.

Family Fun

The first annual Hamptons Harvest is a perfect way to spend your weekends this fall. From October 10-November 7, the Hamptons will celebrate the local flavors, sounds and sights that Long Island has to offer.

Looking to spend an event-filled, kid-oriented day on the Island? Tanglewood Preserve in Rockville Centre transforms the 16-acre Center for Science Teaching and Learning into a Spooky Fest event for the whole family. Admission is $10 to $15 depending on which activities you choose. Featuring a fun, not-so-spooky walk in the woods for children, face painting and a live animal exhibit, the event will take place on October 12th, 18th, 19th, 20th, 25th, 26th, 27th, and November 2nd from 6:30 PM-9:30 PM.

Long Island Children’s Museum’s Ghostly Gala Halloween party in late October is an entertaining, safe, and festive way to enjoy the holiday. This is one event your children will remember well past the spooky season. The special night at the museum includes face painting, goody bag decorating, gallery trick-or-treating, a costume party and more. This event takes place October 26th 6pm-9pm at $10 for members and $12 for the general public.

Wine, Food and Brews

It’s that time of year when indulging in pumpkin-flavored food and drink is completely acceptable, but if you’re a wine connoisseur, head to Pindar Vineyards on Saturday, October 19, for the Rock the Harvest event. From 2pm-6pm, there will be food trucks, a beach glass jewelry pop-up shop, and the band, Bon Journey. The event is free to attend, with additional costs for food, wine, and other purchases. If you’re looking to make it a weekend, the Fig and Olive or Blue Iris Bed and Breakfast are both right across the street.

If sampling the latest micro-brews is more your style, the Great South Bay Brewery hosts its annual Punktoberfest on Saturday, October 19. The event brings together local breweries for seasonal beers, brats, and punk rock bands. Looking to enjoy multiple breweries throughout the day? You can head on over to Brew Crew Cycles to tour around the east end trying local beers.

For foodies, the world is your oyster on October 19 & 20 at the Oyster Festival on the Waterfront at Theodore Roosevelt Park in Oyster Bay. You can shuck your own dinner and see a pirate show, live entertainment, and impressive artisans. Come for a fun mixture of activities like the iconic oyster-eating and oyster-shucking contest. The event is free (except for select activities) and runs from 11am-7pm on Saturday and 11am-6pm on Sunday.

Haunted Halloween Fun

The Rise of the Jack O’ Lanterns at Old Westbury Gardens, presented throughout October, showcases the work of dozens of fantastic local artists. Spend an hour walking through the trail and see more than 5,000 hand-carved Jack O’Lanterns light up the night.

If you’re looking for a medium sized scare, attend the 31st annual Camp Paquatuck Spooky Walk in Center Moriches. Run by the camp volunteers, it’s held on October 18th, 19th, 25th and 26th from 7pm-9pm. Admission is $20 per ticket and all proceeds go to the camp.

For many years, Bayville Scream Park has been perfecting the way they scare their customers always leaving them spooked and satisfied. It’s open through November 3rd with 6 different themed attractions, including Bloodworth Haunted Mansion, Temple of Terror, Evil in the Woods, and Bayville Haunted Asylum. Prices vary depending on how many attractions you wish to visit.

Apples, Pumpkins & Corn:

Picking pumpkins, going on hayrides and navigating corn mazes, while enjoying some caramel covered apples and hot apple cider, is what you’ll find in the fall on Long Island.

Harbes Family Farm has been farming on Long Island for over 13 generations and over the years has evolved into a North Fork destination where families can enjoy anything from fresh picked corn to award winning wines. In the fall, Harbes offers pumpkin picking, apple picking, corn mazes, hayrides, farm animals, kid’s activities and more. Harbes locations in Mattituck, Riverhead and Jamesport.

Open daily every day until Halloween, Hank’s Pumpkintown offers visitors everything from pumpkin picking, apple picking, corn mazes, wagon rides, tractor train rides, giant slides, playgrounds and more. After the fun, head over to the market for fresh pies, candy apples, cider donuts, and roasted corn.

Located in the heart of Long Island Wine Country, Krupski’s Farm offers a wide variety of fruits, vegetables and other produce on their pick-your-own farm. The farm also hosts a variety of seasonal activities including a Haunted Corn Maze, Haunted Barn, hayrides, and a huge selection of pumpkins to pick!

For additional activities that celebrate Autumn on Long Island, visit our Fall on Long Island page.

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