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

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.

Fall has arrived, which means it’s time to go pumpkin picking in Westchester! There are plenty of places to pick your perfect pumpkin in Westchester County, plus a few locations in nearby Dutchess County and Fairfield County, CT. Whether you want pumpkins to carve into jack-o’-lanterns or decorate your home or yard, browse through this guide of Westchester County pumpkin patches, and be on your way to an awesome autumn adventure! And if you want to venture a little further out, you can find the best places to pick pumpkins in Rockland, NYC, and Long Island. Before you head to one of these farms or orchards, it’s a good idea to call to confirm pick-your-own availability and hours.

Pumpkin Picking in Westchester County

1. Outhouse Orchards

139 Hardscrabble Road, North Salem
Hours: Saturday-Sunday, 9am-5:30pm; arrive within the first hour of your admission and finish within your reservation time slot.
Admission: Reserve a ticket online for entrance and parking at the orchard for one vehicle: $15, plus $2.73 fee covers all people inside the vehicle. At the farm, you can purchase bags for apple picking, corn maze tickets, or browse the country store. Pumpkins sold by the pound.

You’ll find a wide selection of pumpkins, gourds, and Halloween decorations that will get you in the fall spirit as soon as you lay eyes on their pumpkin patch (all pumpkins are vine free). Pick your favorite pumpkin and staff will weigh it for you at the check-out tent.

Why we love it: The 2021 corn maze is ready for you to solve. See if you can find your way out.

2. Wilkens Fruit & Fir Farm

1335 White Hill Road, Yorktown Heights
Hours: Anticipated opening for pumpkins is Oct. 1: Wednesday-Monday, 10am-4:30pm. Check Harvest Calendar for exact dates.
Admission: Check back for details.

The 2021 season celebrates the 105th year of harvest at Wilkens. When you’re done choosing your pumpkin, get lost in the corn maze that gets a new and updated design each year.

Why we love it: It also offers pick-your-own apples, peaches, nectarines, and Christmas trees.

3. Stuart's Fruit Farm

62 Granite Springs Road, Granite Springs
Hours: Pumpkins now available; daily, 9am-6pm
Admission: Check back for details

You can select your perfect pumpkin for decorating, carving, or just to have for décor. Visit the farm stand to buy a pre-picked pumpkin, gourds, Indian corn, and corn stalks.

Why we love it: An on-site bakery offers pies, apple cider, apple cider doughnuts, muffins, scones, and other treats for sale.

4. Harvest Moon Farm & Orchard

130 Hardscrabble Road, North Salem
Hours: Farm store: Monday-Sunday, 9am-6pm. Call for pumpkin availability.
Admission: $15 for apple picking. Children ages 3 and younger are free.

Primarily an apple orchard, this farm grows other seasonal produce, and the pumpkin patch is now open.

Why we love it: Each ticket includes access to the orchard, live music, fresh doughnuts, and farm store shopping.

Dutchess County Pumpkin Picking

1. Dykeman Farm

31 Dykeman Lane, Pawling
Hours: Pumpkin picking typically opens the last weekend in September and runs Saturday-Sunday, 10am-5pm, through October. Check the website for details.
Admission: Free parking and free admission.

This fourth-generation family-owned and -operated farm has been offering pick-your-own pumpkins since 1974. Enjoy more than the pumpkin patch here: Take advantage of a photo spot, purchase local honey, enjoy the kids play area, buy some fall décor, and more.

Why we love it: Hayrides are free!


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2. Fishkill Farms

9 Fishkill Farm Road, Hopewell Junction
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
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
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
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!).

2. Castle Hill Farm

1 Sugar Lane, Newtown
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. 

3. Jones Family Farms

Pumpkinseed Hill, 120 Beardsley Road, Shelton
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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