11 Awesome Spots to Go Pumpkin Picking in Westchester County and Nearby

Look no further for the best spots to pick pumpkins in Westchester County, plus options for pumpkin picking in Dutchess and Fairfield counties.

By Stacey Feintuch , Barbara Russo September 22, 2021

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2. Fishkill Farms

9 Fishkill Farm Road, Hopewell Junction
845-897-4377
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Hours: Pumpkin picking now available. Reservations will be required. Reservation arrival times are generally from 9am-4:30pm. The last entry to the orchard is at 5pm, and it closes at 6pm. Reservations are rain or shine.
Admission: If you have an apple picking reservation, you don’t need a pumpkin reservation and can pick and pay for your pumpkins when you’re here. Pumpkins are flat prices depending on their weight class. If you want to just pick pumpkins, pricing is $30, which includes entry for up to 5 people (ages 2 and older, kids younger than 2 don’t need to be counted in the reservation number) as well as $20 worth of pumpkins from pumpkin patch. An additional two people can be added at check-in for $5 each.

Fishkill Farms is an apple orchard and diversified fruit and vegetable farm. Kids will love getting lost in the corn maze and taking a wagon ride throughout the orchard. Hungry? Enjoy a delicious Jerk Chicken meal at the outdoor grill.

Why we love it: You can pick your own eco-certified or organic apples.

3. Greig Farm

227 Pitcher Lane, Red Hook
845-758-8007
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Hours: Pumpkin picking typically begins mid-September and continues through early November: daily, 9am-7pm.
Admission: No entry fee. Pay only for what you pick by the pound. 2021 prices will be announced soon.

Bring friends and family together and spend an afternoon picking pumpkins. This pick-your-own farm in the Hudson Valley has been family run since 1942. While the farm does cut many of the pumpkins off the vine for you, you may find one still on the vine. Have fun cutting it yourself with a set of garden shears.

Why we love it: We can’t get over the gorgeous photos of the farm on social media.

4. Barton Orchards

63 Apple Tree Lane, Poughquag
845-227-2306
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Hours: Sunday-Thursday, 11am-6pm; Friday and Saturday, 11am-8pm. Check back for pumpkin availability.
Admission: You pay for what you pick, but there is a $10 minimum. 

There is lots of fresh produce to pick from on this 175-acre apple orchard and vegetable farm. Visit the ice cream stand, try an apple cider doughnut, and say hello to some friendly farm animals.

Why we love it: There’s a fun aerial adventure open on-site Friday-Sunday. Tickets must be purchased in advance. 

Pumpkin Picking in Fairfield County, CT

1. Blue Jay Orchards

125 Plumtrees Road, Bethel
203-748-0119
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Hours: Monday-Friday, 11am-5pm; Saturday-Sunday, 10am-5pm
Admission: Pumpkins: $0.69 per pound. Apple picking: $12, $20, or $40 depending on which size bag you purchase.

In addition to apple picking, this orchard offers a pumpkin patch where kids (and kids-at-heart) can choose the perfect pumpkin for their jack-o’-lantern. You can also find specialty gourds and warty pumpkins at the farm market.

Why we love it: The farm market sells apple cider doughnuts, pies, local honey, maple syrup, and more—all made locally (the baked goods are made on-site!).

 

 

 

 

 

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2. Castle Hill Farm

1 Sugar Lane, Newtown
203-426-5487
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Hours: Pumpkins, corn maze, and hayrides: Oct. 2-Nov. 7, Saturday-Sunday, 10am-5pm
Admission: Pumpkins: $0.59 per pound. Specialty pumpkins: $0.79 per pound. Corn maze: TBD. 

This farm’s 4-acre pumpkin patch has more than 40 varieties of pumpkins to choose from! Plus, the farm is home to a 7-acre corn maze with a wagon observation deck, hayrides (may not be offered this season; TBD), and a farm market selling fresh produce, free-range eggs, and more.

Why we love it: It’s going to host two nights for Flashlight Maze (Nov. 5-6), where you can enjoy a bonfire, live music, and scavenger hunt, in addition to the maze at night. 

 

 

 

 

 

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3. Jones Family Farms

Pumpkinseed Hill, 120 Beardsley Road, Shelton
203-929-8425
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Hours: Sept. 25-Oct. 31, Monday-Friday, 10am-5:30pm, Saturday-Sunday and Oct. 11, 9am-5:30pm (arrive by 4:30pm to enjoy all the farm has to offer)
Admission: $10 Saturday-Sunday and Oct. 11; $5 Monday-Friday

In addition to a variety of large pumpkins that are ideal for carving, this farm offers a variety of pumpkins, squash, and gourds. Plus, admission includes the corn maze, education displays, photo ops, a Farm Ranger Hike, and access to explore designated areas of the farm’s grounds. And for an extra fee, you can take a hayride. 

Why we love it: If you reserve tickets online, half of your entry fee can be credited toward your pumpkins!

 

 

 

 

 

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