Did You Know? Some of the ground at Wickham’s Fruit Farm in Cutchogue has been under cultivation since 1661. Pick an apple there and you are standing on land that has grown fruit for more than three centuries.
Fall arrives on Long Island’s East End as a change in traffic and light. The farm stands turn over from corn to gourds, the roads empty out midweek, and by September, orchards begin opening their rows.
There are more places to pick out here than most people expect, and they are not interchangeable. What you are choosing between is not a farm. It is a kind of day.
Start with the day you want.
The full farm day – hayrides, corn mazes, music, and a bag of cider doughnuts on the way out.
The working orchard – rows, a wagon, and almost nothing else, on purpose.
The cider stop – picking paired with hard cider poured on the same property.
The small-hands orchard – dwarf trees a child can reach without being lifted.
Jump to a Region
The guide runs west to east, the way most people arrive.
- Riverhead – Sound Avenue orchards and the biggest farm days
- North Fork – older orchards, wagon rides, and hard cider
- South Fork – quiet rows and dwarf trees near Mecox Bay
- Make a Day of It, or Stay the Night – three routes, with somewhere to sleep
- Before You Go – timing, crowds, and orchard rules
Riverhead
Sound Avenue is the spine of it, and this is the maximalist end of the East End apple day.
Harbes Orchard, Riverhead – Twenty-seven apple varieties grown on a trellis system that keeps fruit within reach of younger pickers. Fall visits can include a corn maze, food, and other seasonal activities, depending on the day. Come when picking is the excuse rather than the point.
Lewin Farms, Calverton – U-pick that runs well past apples, with a September corn maze and a long list of seasonal produce. Good if half your group wants to fill a bag and the other half wants to get lost.
Windy Acres Farm, Calverton – A fifth-generation family farm on Route 25, and the smallest of the three Riverhead stops. Check directly for the week’s available varieties before you go.
Local Tip: Varieties rotate week to week as blocks come ripe.
North Fork
Older orchards, a slower pace, and a good place to pair picking with hard cider.
Wickham’s Fruit Farm, Cutchogue – A working farm on the water at Wickham Creek, where a tractor-pulled wagon carries pickers out to the rows and an old cider press still sits on the property. This is the North Fork fall day with the agri-entertainment stripped out.
Woodside Orchards, Aquebogue and Jamesport – Apple picking paired with hard cider tastings and baked goods, the rare orchard that works just as well for a group with no children in it.
Local Tip: Wickham’s is closed Sundays. The rows here are quietest midweek, when the wagon is running for a handful of people.
South Fork
The Hamptons are not where most people think to pick apples, but Water Mill holds two orchards a few minutes apart that could not be less alike.
The Milk Pail U-Pick, Water Mill – The Halsey family has farmed around Mecox Bay since the 1640s, and the orchard is now in the hands of the eleventh and twelfth generations. There are no rides or elaborate attractions here; the orchard is the point. U-pick normally operates Friday through Sunday in season.
Seven Ponds Orchard, Water Mill – Apple picking with a corn maze, hayrides, picnic space, and a farm market. A good choice when the orchard day needs to keep younger children busy too.
Local Tip: The Milk Pail runs three separate places in Water Mill. The Fresh Market is on Montauk Highway and the farm stand is on Mecox Road, but the u-pick entrance is on Horsemill Lane.
Make a Day of It, or Stay the Night
Three routes that pair an orchard with somewhere to eat and somewhere to end up.
The Sound Avenue Day
Riverhead in the morning before the lot fills, then east along the farm stands for pumpkins and cider, dinner toward Jamesport.
The Route 25 Slow Roll
Aquebogue for the cider, Cutchogue for the picking, Greenport for the evening. The least hurried version of the day.
The Mecox Loop
Water Mill orchard first, then down to the bay and the ocean beaches; at their best in October precisely when the crowds have thinned . Check beach parking rules before you go.
October weekends send everyone west at the same hour, and the drive home is where a good farm day turns into a long one. All three are better with a night at the end.
Where to Stay: Find places to stay across the East End
Before You Go
- Every orchard sets its own picking days, varieties, pet policy, and payment methods, and all of it changes through the season. Check the farm’s own page or social media before you drive out.
- The season runs from roughly the start of September into late October, with varieties rotating throughout.
- Roped-off sections mean the fruit is still ripening, so stay in the open rows. Follow each orchard’s rules for picking, bags, and handling the trees.
- Weekend afternoons are the crush. Weekday mornings are a different place entirely.
What Grows Back
The apples are almost incidental. What people drive out for is the light in October and the sight of working farmland that has looked more or less the same for years. Much of the East End’s farmland is now protected through preservation programs, so the rows you walk are not waiting to become something else. On Long Island that is not a small thing to still have.
Looking for something to bring home besides fruit? Our guide to the East End’s sunflower and cut flower farm stands covers where to cut your own.
Find Your East End.