The Best Apple Picking On Long Island

The return of cool and cozy fall nights means only one thing—the beloved family tradition of apple-picking season is back on Long Island.

Each and every autumn, throngs of people flock to the island in search of “U-pick” orchards, apple festivals, and other types of fun fall activities fit for the entire family. And if you’re staying on Long Island at the Inn at Fox Hollow, there is perhaps no better autumn outing than one spent diligently picking apples at a local orchard. 

All you need to hit the road on your apple journey is a comprehensive list of where to find the shiniest, sweetest apples on the island. Map out your day and pick a winner! Just remember to call ahead for hours, to confirm prices, and for apple-variety availability. 

Hank’s Pumpkintown
240 Montauk Hwy., Watermill
631-726-4667
There are plenty of apples to pick at this pumpkin-named orchard, including such varieties as gala, McIntosh, honey crisp, and more. In all, there are 14 different kinds of apples, at $25 to pick a one-pack bag. There’s also a maze park, playground, wagon and tractor rides, and face painting. Hank’s is open until late October, but get there before you’re left with slim pickings.

Seven Ponds Orchard
65 Seven Ponds Rd., Watermill
631-726-8015
The trees on this orchard are known as “superdwarf” as they are incredibly reachable for kids of all heights. Along with seasonal activities like picnic areas, corn mazes, and hayrides, apples like golden delicious, red delicious, and honey crisp are readily available. Seven Ponds is open through Thanksgiving. 

Milk Pail U-Pick Farm
50 Horsemill Lane, Watermill
631-537-2565
This apple orchard and farm started way back in the 1600s with one of Long Island’s first families, the Halseys. Since then, they’ve offered more than 20 types of apples on their dwarf trees, for $49 in a large bag and $12 in a small bag. They also have pumpkins, gourds, squash and more, including flowers. 

Wickham’s Fruit Farm
28700 Main Rd., Cutchogue
631-734-641
Another one of Long Island’s historic farms, Wickham’s Fruit Farm dates back to 1661 and sits against the sparkling waters of Peconic Bay. Not only is there a wide variety of apples, but also cider donuts and apple cider from what the locals say is the oldest cider press on Long Island. 

Lewin Farms
812 Sound Ave., Calverton
631-929-4327
One of the main draws at Lewin Farms is its unique corn maze, which is designed anew each year. Along with seasonal apples, the orchard lets you pick berries, tomatoes, peppers, and eggplant. Don’t leave without grabbing a cob of roasted corn at the farm stand. 

Woodside Orchards
729 Main Rd., Aquebogue
116 Manor Lane, Jamesport
631-722-5770
Along with some unique apple varieties like Arkansas Black, Baldwin, and Cortland, Woodside Orchards also has pies, cookies, apple bread, donuts, and more. Meanwhile, they also offer hard cider tastings for the adults in the crowd. 

Harbes Family Farm and Orchard
5698 Sound Ave., Riverhead
631-369-1111
This 15-acre apple orchard has been going strong for 30 years. Along with apples, the Harbes Family Farm also delivers a barnyard adventure for kids, a vineyard for adults, and plenty of fresh produce and sweet treats like cider donuts. What’s more, this weekend (Sept. 14 and 15) is the orchard’s annual Apple Festival, which features fun for the entire family.