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Fall Festivals and Fun on Long Island

September 3, 2021

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

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 $12 to $20 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 the weekends of October 8-10, 15-17, 22-24, and 29-31 from 6:30 p.m to 9:30 p.m.

The Milleridge Inn is also transforming its notorious village into a Halloween spectacular! Every weekend starting October 1st, the Milleridge village in Jericho will be hosting a variety of family-friendly activities including a Haunted House, a Spooky Train Ride, inflatable ax throwing, a bounce house, mini-golf, pumpkin decorating, a corn maze, and more! There is no fee to enter the grounds, but some special attractions do require you to purchase a wristband.

Can’t get enough of the great outdoors? Why not enjoy a guided tour of Spirit’s Promise Equine Rescue? The tour includes a hands-on walk-through and education of the rescued animals. Visitors can expect to get up-close-and-personal with horses, ponies, goats, chickens, and pigs–all while learning about the animals, their environment, and culture. Spirit’s Promise Equine Rescue invites guests to pack a picnic and hang out after the tour in the outdoor pavilion. Tours can be reserved on the Spirit’s Promise Rescue website by selecting your desired time and date. What to Bring: Suitable shoes for walking (closed-toe ONLY), water bottle, sunscreen, and any snacks you may want. Please dress for the weather. You must bring a photo ID for onsite confirmation of your reservation.

Spirit's Rescue Equestrian Farm

The Long Island Maritime Museum in West Sayville is hosting its 31st Annual Halloween Boat Burning on Friday, October 29th (the rain date is set for the following Saturday, October 30th). Join the West Sayville Fire Department and Suffolk County Parks Department as they set a boat that is no longer safe to charter ablaze. This one-of-a-kind event includes light refreshments, a boat raffle, and other live entertainment. It is free for children under 5, and the admission price for all other guests is $5 per person.

Downtown Riverhead’s Annual Halloween Fest will be taking place on October 23rd (the rain date is October 24th). This free event is costume-friendly and is home to jack-o-lantern displays, an escape room, a grand costume parade, a masquerade ball, coffin races, and so much more. Kids are invited to trick-or-treat down Main Street from 4 p.m. to 6 p.m.

Head on over to SweetBriar Nature Center in Smithtown on October 24th for a fun afternoon of tails, trails, and treats! This event is free for adults and $10 per child, it features close encounters with animals, a ghostly garden, games, and a special puppet enchanted trail. Tickets can be purchased in advance online.

Wine, Food, and Brews

Famous Food Festival’s “Taste of the World” returns to Tanger Outlets in Deer Park this Labor Day weekend. Featuring over 60 food vendors, visitors should be prepared to taste some of the best dishes that New York, Tri-State, Long Island has to offer. This weekend fest is filled with more than just unique eats, but a variety of activities that the whole family can enjoy. Whether it’s live music, the beer and wine lounge, live cooking demos, the local artists’ gallery, vampire-themed escape room, Alpha Axe Throwing, Mobile Man Cave Tailgating Experience, or the kid’s play section, there truly is something for everyone. This all-ages event is only $7 to attend each day (children 10-years-old and under can enter for free) and discounted pricing for multiple-day entry is available online. Tickets are also available at the door for $12 per person.

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 16, for the Rock the Harvest event. From 2 p.m.-6 p.m., 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.

Rather take a guided tour of multiple breweries throughout the day? You can head on over to Brew Crew Cycles to tour around the east end trying local beers.

Brew Crew Cycles brewery bike tour

Long Ireland Brewery will be hosting its 7th Annual Halloween Costume Contest on Saturday, October 30th. The entry fee is $25.00 per person and includes admission and two beer tickets. The event will have live performances and provisions available through The Big Black Food Truck. First, second, and third place winners as well as the winner of the Best Group Costume will receive a prize for costume creativity!

Haunted Halloween Fun

The Great Jack O’ Lantern Blaze is back at Old Bethpage Restoration! Meander through a 19th-century village and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on-site by our team of artisans. New for 2021, gawk at our 80-foot circus train and our incredible sea monster. Complete with synchronized lighting and an original soundtrack, this event is not to be missed! The display opens on September 22 and runs thru November 7. Tickets are on sale now and can be purchased online through Blaze, admission prices begin at $32 per ticket but children under 2-years-old can enter for free. Visit the Blaze: Long Island site for more information regarding COVID protocols, booking, and parking information.

Blaze pumpkin display

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 15th, 16th, 22nd, and 23rd from 7 p.m. to 9 p.m. Admission cost is $20 per ticket and all proceeds go to the camp.

Are pumpkins not scary enough? Well, 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 six 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.

Ever wonder what it would be like to be a paranormal investigator? Well now is your chance! Join the Long Island Paranormal Investigators on September 24 for an investigation of the Thomas Halsey Homestead while they continue their search for evidence of what happens to us after we die. Groups will be given just over an hour inside the 1683 wood-frame home and taken to the various hot spots of paranormal activity within the museum. Please see the Southampton History Museum website for more details on the program, ticket prices, tour times, and the COVID safety measures that will be put in place.

Thomas Halsey Homestead Haunted Tour

If one haunted ghost tour isn’t enough, don’t fret! You can also join the Long Island Paranormal Investigators on September 24 for an investigation of the Rogers Mansion while they continue their search for evidence of the spiritual realm. Groups will be given just over an hour inside the 1843 Whaling Captain’s mansion and taken to the various hot spots of paranormal activity within the museum. Please see the Southampton History Museum website for more details on the program, ticket prices, tour times, and the COVID safety measures that will be put in place.

Rogers Mansion

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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