Fall on Long Island: Where to Go for Pumpkin Picking, Apple Cider Donuts, Wineries & More in 2026
By The Galluzzo Team at Compass | October 19, 2026
There's something about fall on Long Island that makes you want to get out of the house and enjoy the weekend.
Maybe it's the cooler weather, the changing leaves, or the excuse to head out east for fresh apple cider donuts and a glass of wine. Whatever it is, October is one of the best times to explore the places that make Long Island special.
And you don't necessarily have to drive all the way to the North Fork to enjoy it.
From pumpkin farms right here in Dix Hills and Melville to vineyards in Mattituck, cider tastings in Aquebogue, and Halloween events happening throughout Suffolk and Nassau counties, there's plenty going on during the last few weeks of October.
We've put together a guide to some of the places worth visiting this fall, along with upcoming events you can still catch before the season ends.
Pumpkin Picking on Long Island: Where to Spend a Fall Afternoon
Schmitt Family Farm — A Fall Tradition in Dix Hills
6 Bagatelle Road, Dix Hills, NY
For families in Commack, Dix Hills, Huntington, and Melville, Schmitt Family Farm is one of the most convenient places to enjoy a classic fall afternoon.
Located on Bagatelle Road, not far from the Long Island Expressway, the farm has become a familiar seasonal destination for local residents.
During the fall, you'll find pumpkins, hayrides, seasonal decorations, and plenty of opportunities for family pictures. The apple cider donuts and hot cider are worth making time for, too.
What we particularly like about having a farm like this in Dix Hills is that you don't have to commit to an entire day of traveling. You can spend a few hours enjoying the activities, grab something to eat, and still have the rest of your afternoon.
For families with younger children, that's a big plus.
The farm's fall activities are scheduled to continue through the beginning of November, although certain attractions and food offerings may vary by day.
Our suggestion: If you live in Commack, Dix Hills, or Huntington and want a fall outing close to home, put this one on your list.
Harbes Family Farm — A North Fork Favorite
715 Sound Avenue, Mattituck, NY
If you're planning to head out east, Harbes Family Farm is one of those places where you can easily spend a good portion of your day.
Harbes has built a reputation around its family-friendly farm attractions, fresh produce, seasonal food, and North Fork atmosphere.
Depending on which Harbes location you visit, activities can include pumpkin picking, apple picking, corn mazes, barnyard attractions, and vineyard experiences.
The Mattituck farm is especially popular with families looking for entertainment and seasonal food, while Harbes Orchard in Riverhead offers apple picking and a corn maze.
And, of course, there's the food. Fresh cider donuts, roasted sweet corn, and other farm treats are part of the reason people look forward to visiting every fall.
One thing to keep in mind is that the different Harbes locations don't all offer the same attractions. Check which location has the activities you're interested in before heading out.
Our suggestion: Go earlier in the day, especially on a Saturday or Sunday. The North Fork gets busy during October, and arriving before the afternoon crowds can make a difference.
Hank's Pumpkintown — A Full Day of Fall Fun in Water Mill
240 Montauk Highway, Water Mill, NY
If you're looking for somewhere the kids can run around, explore, and stay entertained for hours, Hank's Pumpkintown deserves a spot on your list.
Located in Water Mill, Hank's offers a large fall activity area with corn mazes, play attractions, wagon rides, pumpkin picking, and seasonal apple picking when available.
It's more of a full-day outing than a quick stop for pumpkins.
The farm market is another reason to visit. You'll find seasonal baked goods, apple cider donuts, pies, and other fall treats that make the trip worthwhile.
Hank's is scheduled to remain open through November 1, 2026, so there is still time to visit before the season wraps up.
If you're already planning a trip to Southampton or the Hamptons, it's an easy activity to build into your day.
Stakey's Pumpkin Farm — Pumpkin Picking in Aquebogue
270 West Lane, Aquebogue, NY
Stakey's is a great choice if the main reason for your trip is to actually head into a field and pick pumpkins.
Located in Aquebogue, this family-owned farm is known for its expansive pumpkin fields and more traditional pumpkin-picking experience.
You'll find a corn maze, hayrides, and seasonal treats, including apple cider donuts and fresh cider.
It's a good stop to make before heading farther east into Mattituck or Cutchogue, especially if you're planning a day that combines farm activities with a winery visit.
White Post Farms — Family Activities in Melville
250 Old Country Road, Melville, NY
White Post Farms is another familiar name for Long Island families.
Located in Melville, the farm offers a combination of animal attractions, children's activities, and seasonal fall entertainment.
Its Fall Farm Festival is particularly popular during October, with pumpkin picking and themed activities.
For families in Huntington, Commack, Dix Hills, and nearby Nassau County communities, White Post Farms is a convenient alternative to driving out east.
It's also a good option if your children enjoy animal encounters as much as pumpkin picking.
Where to Find Great Apple Cider Donuts on Long Island
Let's talk about one of the best parts of fall: apple cider donuts.
There are plenty of farms selling them across Long Island, but a few places stand out as especially worthwhile stops.
Woodside Orchards — Aquebogue
729 Main Road, Aquebogue, NY
Woodside Orchards is a particularly good choice if you want something for both the adults and the kids.
The orchard is known for its apple cider donuts and hard cider tastings, offering a more relaxed experience than some of the larger fall attractions.
You can stop in for donuts and cider, browse seasonal offerings, or enjoy a tasting flight of locally produced hard cider.
It's also conveniently located for anyone planning a North Fork afternoon.
Wickham's Fruit Farm — Cutchogue
28700 Main Road, Cutchogue, NY
Wickham's has the kind of old-fashioned farm atmosphere that fits perfectly with a fall drive through the North Fork.
The farm has a long agricultural history and is known for its seasonal fruit, fresh baked goods, apple cider donuts, and pies.
If you're someone who prefers traditional farm stands over larger entertainment-style attractions, Wickham's is worth checking out.
Windy Acre Orchard — Calverton
3810 Middle Country Road, Calverton, NY
Windy Acre is another excellent stop for fresh apple cider donuts.
Located in Calverton, the orchard offers seasonal produce, pick-your-own opportunities, and farm activities.
It's a convenient place to stop when traveling through Riverhead or heading toward the North Fork.
Brightwaters Farms — Bay Shore
1624 Manatuck Boulevard, Bay Shore, NY
For anyone on the South Shore who doesn't want to drive east, Brightwaters Farms is worth knowing about.
The farm offers seasonal produce, baked goods, apple cider donuts, and fall harvest activities.
It's a great reminder that some of Long Island's best seasonal experiences can be found close to home.
Long Island Wineries That Are Especially Beautiful in the Fall
You don't have to be a wine expert to appreciate a fall afternoon on the North Fork.
The vineyards are beautiful this time of year, the summer crowds have started to thin out in some places, and there are plenty of opportunities to enjoy a tasting with friends or family.
Here are a few wineries worth considering.
Macari Vineyards — Mattituck
150 Bergen Avenue, Mattituck, NY
Macari is a beautiful place to spend an afternoon, particularly when the vineyard begins taking on its fall colors.
The family-owned winery offers a scenic estate setting, with vineyard views and outdoor seating.
It's a good choice if you're looking for somewhere to slow down, enjoy a glass of wine, and take in the North Fork scenery.
Bedell Cellars — Cutchogue
36225 Main Road, Cutchogue, NY
Bedell Cellars is one of the North Fork's established wineries, with a beautiful tasting room and vineyard setting.
It's an appealing destination for couples or groups looking for a more traditional wine-tasting experience.
The property also makes a lovely stop during the fall harvest season.
Raphael — Peconic
39390 Main Road, Peconic, NY
Raphael is hard to miss.
Its Mediterranean-inspired architecture gives the winery a distinctive appearance, and the surrounding vineyard creates a beautiful setting for an afternoon tasting.
If you're planning a date or celebrating a special occasion, Raphael is one of the more memorable places to visit on the North Fork.
Pindar Vineyards — Peconic
37645 Main Road, Peconic, NY
Pindar has been part of Long Island's wine industry for decades and offers a wide selection of wines.
It's a good stop for visitors who enjoy trying different varieties, especially when traveling with a group that has different tastes.
Sparkling Pointe — Southold
39750 County Road 48, Southold, NY
For something a little different, Sparkling Pointe specializes in sparkling wine.
The vineyard offers a polished tasting experience and a beautiful property in Southold.
It's an excellent choice for a fall date, birthday outing, or special occasion.
Planning tip: Many wineries have different reservation requirements, group policies, and weekend schedules. Always check before visiting, particularly during October.
Don't Forget Long Island's Breweries and Cideries
Not everyone wants to spend their afternoon at a winery, and that's one of the nice things about Long Island. There are plenty of other options.
Greenport Harbor Brewing Company is a good stop if you're exploring the North Fork and prefer craft beer. Its Peconic brewery offers a different atmosphere from the traditional vineyard experience.
Jamesport Farm Brewery is another option worth considering. The farm brewery setting fits naturally into an afternoon spent visiting local farms and farm stands.
If you're staying closer to home, Blue Point Brewing Company in Patchogue is an option for craft beer, food, and an afternoon or evening exploring the village.
And for hard cider, Woodside Orchards in Aquebogue is a natural fall destination.
Upcoming Long Island Fall Events: October 23 Through November 2026
If you're looking for something specific to do over the next few weekends, there are still several events on the calendar.
Friday, October 23 — Sunset Music at Wölffer Estate
Wölffer Estate Wine Stand, Sagaponack | 4:00 PM
Start the weekend with live music at the Wine Stand. It's a relaxed way to enjoy an autumn afternoon on the South Fork.
Saturday, October 24 — Help Us Harvest at RGNY
RGNY, Riverhead | 10:00 AM and 2:00 PM
For something beyond a typical wine tasting, RGNY is hosting its Help Us Harvest experience.
This is an opportunity to get a closer look at the North Fork's grape harvest and the work that goes into producing local wines.
Check availability and ticket requirements before making the trip.
October 23–25 — Spooky Fest in Rockville Centre
Center for Science Teaching & Learning, Rockville Centre | 6:00–9:00 PM
Spooky Fest offers Halloween entertainment for families, with options for those who prefer a less frightening experience as well as scarier attractions.
It's a good alternative to a farm outing, particularly for families in Nassau County.
October 24–25 — Merrick Fall Festival & Street Fair
Merrick | Street fair 10:00 AM–5:00 PM
Enjoy a fall weekend with street fair vendors and carnival entertainment.
The carnival is scheduled from October 23 through October 25, while the street fair takes place Saturday and Sunday.
Saturday, October 24 — Live Music at Bedell Cellars
Bedell Cellars, Cutchogue | 1:00 PM
Bedell has a live music performance listed for Saturday afternoon, making it a nice option if you're planning a North Fork winery trip.
Sunday, October 25 — Race for the Greenway 5K
North Fork | 8:30 AM
For anyone who would rather spend the morning outdoors and active, the Race for the Greenway offers a community-focused 5K run and walk.
Saturday, October 31 — Paws & Pours Halloween Party
Bridge Lane Wine, Mattituck | 2:00–5:00 PM
Here's something different for dog owners.
Bridge Lane is hosting a Halloween-themed Paws & Pours event, giving visitors a chance to enjoy a seasonal vineyard outing with their dogs.
Check the event rules before bringing your pet.
Sunday, November 1 — Last Scheduled Day at Hank's Pumpkintown
Hank's Pumpkintown, Water Mill
If you haven't made it to Hank's this fall, November 1 is the last day of its announced 2026 season.
Saturday, November 7 — Día de los Muertos at RGNY
RGNY, Riverhead | 7:00 PM
RGNY is celebrating Día de los Muertos with an evening of music, entertainment, wine, and seasonal traditions.
The announced program includes House of Yes, a tarot reader, live poetry, face painting, and other experiences.
This is a ticketed event, so check availability before attending.
A quick note: Event schedules, ticket availability, and farm activities can change, particularly due to weather. Check the organizer's website before leaving home.
How We'd Spend a Fall Weekend on Long Island
If you're trying to narrow everything down, here are three ways to put together a great fall day.
For a family day close to home: Start at Schmitt Family Farm in Dix Hills, spend some time at White Post Farms in Melville, and finish the day with dinner in Huntington Village. You can enjoy a full day of fall activities without driving out east.
For a North Fork afternoon: Stop at Woodside Orchards for apple cider donuts, visit Harbes in Mattituck, and finish with a tasting at Macari or Bedell. If you have extra time, take a drive through Greenport before heading home.
For a Hamptons fall day: Visit Hank's Pumpkintown in Water Mill, spend the afternoon exploring Southampton, and make dinner reservations at one of the local restaurants.
The best part is that you can make the day as busy or relaxed as you want.
What Makes Fall on Long Island So Special?
One of the things we appreciate about living and working on Long Island is how different each community can feel, even when they're only a few towns apart.
In Commack and Dix Hills, you have established neighborhoods, parks, local businesses, and family traditions that make the area feel like home.
Huntington and Northport offer beautiful villages, waterfront scenery, restaurants, and community events throughout the year.
Head farther east, and the landscape changes into farmland, vineyards, orchards, and the small-town atmosphere of the North Fork.
It's one of the reasons so many people choose to put down roots here. You're never too far from something new to explore.
And while fall is a particularly beautiful season, there's something to enjoy on Long Island throughout the year.
Your Long Island Real Estate Connection
At The Galluzzo Team at Compass, we spend our days helping people buy and sell homes throughout Long Island, but being part of the community means more to us than real estate transactions.
We believe that loving where you live is just as important as loving the home itself.
Whether you're enjoying a weekend in Huntington, visiting a local farm in Dix Hills, or discovering a new favorite winery on the North Fork, these are the experiences that make Long Island home.
If you're thinking about making a move, exploring a new neighborhood, or simply curious about what your home may be worth in today's market, we'd be happy to help.
The Galluzzo Team at Compass
Elena Galluzzo | Chris Galluzzo | Christo Galluzzo
631-774-3333
Helping Homes Find Their People.
This guide was updated October 19, 2026. Seasonal attractions and event schedules are subject to change.
