From pumpkin picking and farm days to street fairs, art walks, and Halloween events, these are the fall stops worth adding to your Long Island town tours.
One of the best times to explore Long Island is fall. Between farm festivals, pumpkin patches, street fairs, and community events, these weeks give families plenty of opportunities to be out and about with your (potential) future neighbors.
If you’re already planning a town tour, use one of these events as your starting point – grab breakfast, walk downtown, explore a neighborhood or park, and then head to the festival, pumpkin patch, or other seasonal happening. Your kids will have a blast and, at the same time, you’ll get a better sense of what life could be like post-move.
Here are some of our favorite 2026 fall activities in the Long Island communities Suburban Jungle families are exploring right now.
Melville
When: Weekends, September 19– October 31, 2026
Where: 26 Pinelawn Road, Melville
Schmitt’s is the full farm-festival version of fall. The 2026 season includes pumpkin picking, wagon rides, the farm’s seven-acre corn maze, playground areas, games, slides, and plenty of seasonal food and photo stops. This year’s corn maze has an America250 theme celebrating the country’s 250th anniversary.
White Post Animal Farm Fall Farm Festival
When: Weekends, September 19–October 2, 2026
Where: 250 Old Country Road, Melville
White Post is an all-day outing rather than a quick pumpkin stop. Fall Festival admission includes the animal farm, bird aviaries, Dinosaur Adventure, giraffe experience, primate barn, unlimited hayrides, family shows, outdoor play areas, and picnic spaces. Pumpkins, pony rides, train rides, and animal feed are available separately.
Huntington
When: October 9–12
Where: Heckscher Park, Huntington
The Long Island Fall Festival is one of the biggest fall events in the area, taking over Heckscher Park for Columbus Day weekend with live music, carnival rides, food, craft and business vendors, kids’ entertainment, and a beer, wine, and spirits tent featuring local products.
Festival hours run Friday from 5–10 p.m., Saturday and Sunday from 11 a.m.–10 p.m., and Monday from 11 a.m.–5 p.m. There are also free magic shows for kids throughout the weekend and an art component at the Heckscher Museum.
When: Monday–Thursday, 3:00 PM–5:00 PM and Friday–Sunday, 10:00 AM–7:00 PM
Where: 1500 E Jericho Tpke, Huntington
For a much more traditional farm experience, Elwood Pumpkin Farm is known for pumpkins grown right in the field, along with a kid-friendly corn maze and wagon rides. This is a perfect option if what you want is straightforward pumpkin picking rather than a large festival with rides and shows. It also makes an easy add-on to a Huntington town tour.
Port Washington
When: Saturday, October 3, 10:00 AM–3:00 PM
Where: United Methodist Church, 35 Middle Neck Road
Port Washington’s annual Pumpkin Festival is free and geared toward families, with hayrides, a bounce house, petting zoo, pony rides, games, a barbecue, bake sale, and a new trackless train for 2026.
Fall Festival at North Hempstead Beach Park
When: Saturday, October 3, 12:00 PM–5:00 PM
Where: North Hempstead Beach Park, 175 West Shore Road
Yes, Port Washington gives you two fall events on the same day.
The Town of North Hempstead’s Fall Festival brings pumpkin patches, crafts, a vendor fair, bouncy slides, train rides, character meet-and-greets, a spooky slime bar, food trucks, and a beer and wine tent to the waterfront park.
If you’re exploring Port Washington, plan to start at the Annual Pumpkin Festival, spend some time downtown, and then head toward North Hempstead Beach Park for the afternoon. It’s a good way to see several different parts of the community in one day.
Cold Spring Harbor
Cold Spring Harbor Library Fall Festival
When: Saturday, October 10, 11:00 AM–1:00 PM
Where: Cold Spring Harbor Library
The library’s fourth annual family Fall Festival keeps things simple: pumpkin decorating, harvest-themed crafts, snacks, cider, and live bluegrass music. It’s a great spot to add to your tour – and this event gives you a reason to see the library, spend time in Cold Spring Harbor, and then continue downtown or explore the surrounding neighborhoods.
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Manhasset
When: October 17, time to be confirmed
Where: Plandome Road
Manhasset’s Chamber of Commerce is bringing back its annual Halloween trick-or-treat to Plandome Road – and you don’t want to miss it. Participating merchants hand out candy to costumed kids, and the Chamber decorates the planters along the downtown corridor for the season.
Garden City
23rd Annual Garden City South Fall Festival
When: Sunday, October 25, 10:00 AM–4:30 PM
Where: Nassau Boulevard, Garden City South
The Garden City South Fall Festival combines a traditional street fair with family activities, including vendors selling handmade and general merchandise, giant inflatables, pony rides, a petting zoo, food trucks, and live music. Admission is free.
Rockville Centre
When: Fridays, Saturdays, and Sundays, October 2–4, 9–11, 16–18, and 23–25
Where: Center for Science Teaching & Learning at Tanglewood Preserve, 1450 Tanglewood Road
Each year, the Center for Science Teaching & Learning transforms Tanglewood Preserve for its annual fundraiser, with both spooky and kid-oriented attractions. Past and current programming includes the Haunted Woods, a gentler Enchanted Walk, costumed characters, crafts, face painting, glowing slime, and other Halloween activities.
Merrick
When: October 23–25
Where: Merrick LIRR station area, Sunrise Highway and Merrick Avenue
Merrick’s annual Fall Festival takes over the area around the train station for three days. Carnival rides begin Friday evening and continue through the weekend, while the Saturday and Sunday street fair runs from 10 a.m.–5 p.m.
If Merrick is on your list, this is a great way to explore the area around the train station while the community is out in full force.
Glen Head / Old Brookville
When: Open daily, 10:00 AM–5:00 PM
Where: 91 Hegemans Lane, Old Brookville
Youngs Farm is not a pick-your-own pumpkin patch – and that’s exactly why it belongs on this list as a different kind of fall stop. This family-run certified-organic farm has been operating since 1893 and still farms about 15 acres. In fall, you’ll find seasonal produce, including pumpkins, along with a market, scratch bakery, and kitchen turning out soups, pot pies, quiches, breads, cookies, muffins, and the farm’s specialty: pies.
Westbury
Hicks Nurseries
When: September 12–November 1, 2026
Where: 100 Jericho Turnpike, Westbury
Hicks’ annual Fall Festival returns with free admission and parking, seasonal games, photo areas, Otto the Ghost’s animated story walkthrough, and a hay maze. Weekend and school-holiday activities expand with kids’ crafts, food, roasted Long Island corn, and other seasonal programming. This is an especially good fall outing for younger kids, whether you want to spend an hour or make a longer afternoon of it.
Use Fall to Explore More Than the Pumpkin Patches
Whichever stop you choose, leave some room in the schedule. If you’re visiting Huntington, walk downtown before the festival. In Port Washington, spend time on Main Street or by the water. Grab lunch in Merrick after the carnival. If you’re heading to Youngs Farm, use the trip to explore Glen Head, Old Brookville, or nearby North Shore neighborhoods.
These fall events are a perfect excuse to get there. See where families gather, how busy downtown feels, whether you like the surrounding neighborhoods, and whether you can imagine coming back on an ordinary weekend when there isn’t a festival happening.
For more insights, visit Suburban Jungle’s New York City suburbs section and the New York City blog page on our website.
Ready to start exploring Long Island? Schedule your free initial strategy call today.