Top 20 Things to Do in the Fall on Long Island

UPDATED JULY 2019: There's nothing like a quintessential fall on Long Island. Have fun at these 20 must-do family events, including country fairs and harvest festivals, Halloween celebrations, apple and pumpkin picking at local farms, and more!

1. Viva Italia!

Grande Festa Italiana, held annually in early September at North Hempstead Beach Park in Port Washington, is both the largest and oldest Italian feast on Long Island. Along with the rides, fireworks, and live music, kids can enjoy sampling a variety of Italian foods and watching cooking demonstrations. Find details on more cultural festivals in our area in our roundup. 

2. Everything You Need

Typically held in mid-September at Long Island University in Brookville, Long Island Parents Day is your one-stop shop. While your children are enjoying classes, games, and activities, you can meet with local vendors (think doctors, after-school programs, dentists, special needs services, and more) to find everything you need for the year. 

3. Apples Abound

Pick fresh apples (along with many other fruits and veggies) in September at Lewin Farms in Wading River. The first “pick your own” farm on Long Island, Lewin Farms is the place to make a childhood memory. Bake a pie with the bounty, and then head to another farm or orchard! 

4. A Blast from the Past  

The iconic Long Island Fair at Old Bethpage Village Restoration has been going on since 1842 (yes, really!), making it the longest-running county fair in New York state. Happening in late September, the fair features traditional music, pony rides, farm animals, fair food, pig racing, circus shows, and more.  

5. Fall Fest

Southampton embraces fall with a full weekend of art, music, food, entertainment, and history near the end of September. The aptly named Southampton Septemberfest will provide fun all weekend in Agawam Park with a variety of activities such as the annual Chowder Contest, caricatures, face painting, food trucks, cornhole games, EMS Safety demonstrations, and a special KIDS ZONE with pumpkin decorating, hula hooping, and an interactive sports expo.

6. Walking with Purpose

Walk Now for Autism Speaks at Jones Beach in Wantagh in mid-October is an amazing way to raise money for this increasingly prevalent condition. Your whole family can do a good deed for a great cause—and get some exercise while you’re at it. Not ready to quit yet? Find more ways to get moving. 

7. Spooky Smiles

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

8. Gourds Galore

Pick your own pumpkins at Stakey’s Pumpkin Farm in Aquebogue and enjoy a brisk walk through the 26-acre pumpkin farm throughout October. With more than 18 varieties of pumpkins to choose from right off the vine, this pumpkin and gourd paradise is well worth the drive. Head to our site to find more u-pick pumpkin farms in the area. 

9. A Community Celebration  

The Long Island Fall Festival at Heckscher Park in Huntington is an ideal way to spend a sunny autumn afternoon. Held in early October, families come from all over the island for the carnival games, farmer’s market, old-time rides, and yummy homemade treats. 

10. A Seaside Soiree

Captree State Park in Babylon celebrates the Dockside Family Festival in early September. Embrace your nautical side with family-friendly music, merchandise vendors, pony rides, and even crab races! 

11. Oyster Overload

In Theodore Roosevelt Park in—where else?—Oyster Bay, you can shuck yourself silly (while the kiddos will find more kid-palatable fare) at the Oyster Festival. And it’s not just shellfish. Find pirate shows, tall ships, and midway rides in mid-October.

12. A Spooky Celebration

The Ghostly Gala Halloween party at Long Island Children’s Museum in late October is a fun, safe, and festive way to enjoy the holiday. With face painting, gallery trick-or-treating, and a costume party, this is one event you’ll remember well past the spooky season.

13. ’Tis the Season to Explore

Long Island has many beautiful hiking trails, and one of the best is Garvies Point Museum and Preserve in Glen Cove. Leading down to a quiet beach, this easy-for-kids trail is one of the most serene on the island.

14. Party 101

In early November, head to the free Celebrate! Party Showcase at the Melville Marriott in Melville to plan any and all milestone occasions you have coming up for the year. Whether it’s a special birthday party, bar/bat mitzvah, wedding, or any other special event, you’ll find more than 100 party specialists to help you plan it all in one place.

15. Autumn Art Walk

Take a stroll through the 145 acres of fields, woods, and ponds at The Nassau County Museum of Art in Roslyn Harbor and be amazed by the inspiring sculptures created by established artists. And if you’re looking to do some leaf peeping outside the area, head to our site for our suggested locations.

16. We’re Out to Discover

Relax, sit back, and enjoy as the Ward Melville Heritage Organization’s Discovery boat takes you for a cruise through Long Island’s wetlands (offered select dates, May through October). Learn about the history, geology, and ecology of the gorgeous area we call home. The pontoon departs from Stony Brook Harbor and cruises through the organization’s 88-acre wetlands preserve for a 1½-hour tour. 

17. The Best Way Out, Is Through

With the exception of pumpkin picking, nothing says fall like a romp in an old-fashioned corn maze. One of the bigger examples on the island is at Fairview Farm in Bridgehampton. The site also has a corn cannon and yes, it is as cool as it sounds.

18. Lizards, Snakes, and Turtles—Oh My!

If your kids think cute and cuddly is boring, then Jungle Bob’s Reptile World in Centereach is sure to please them. And the fact that there’s no charge for admission will please you! This unique showroom allows you to see unusual creatures living in their own habitats. 

19. Art Fest

From visual, musical, and performing arts to community festivals and epicurean delights, the annual Arts Alive LI festival in October is a month-long tribute to Long Island’s arts and entertainment world. It takes place on stages, in galleries, at film houses, and in neighborhood restaurants across the island. 

20. Turkey Day Parade

Courtesy Macy’s

Arguably the world’s most famous parade, Macy’s Thanksgiving Day Parade boasts behemoth balloons, beautiful floats, and the biggest names in entertainment—and it all takes place a train ride away, in the heart of Manhattan.

MORE SEASONAL FUN ON LONG ISLAND