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Parlee Farms
Photograph: Courtesy Parlee Farms

13 best places to go pumpkin picking near Boston for fall fun

The patches at one of these charming local farms are chock-full of pumpkins and ripe for the picking this autumn near Boston.

JQ Louise
Edited by
JQ Louise
Written by
Megan Johnson
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Can you feel the crisp autumn breeze cascading through your hair as you toss your scarf over your shoulder? If so, that means it’s New England in the fall, when the foliage is fiery and the apple cider is hot. While there’s countless activities that will let you bask in the beauty of autumn, pumpkin picking is a must-do for all card-carrying New Englanders and visitors alike. Ditch the pre-picked varieties at the grocery store checkout counter and head to one of these local farms near Boston, where you can hitch a ride on a wagon and choose your own stylish squash. For more seasonal activities, check out where to see the best fall foliage in Boston, where to go apple picking near Boston, and where to get the best hot chocolate in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Where to go pumpkin picking near Boston

Located in South Natick, Lookout Farm is one of the closest options for pumpkin picking. Hop on the farm train to head out to the field; they grow around 25,000 pumpkins each season, so you’re sure to find a good one. There are additional activities for the kids, plus a restaurant and taproom with hard cider and fantastic fall bites.

Twelve generations of the same family have kept this North Andover farm going strong. Enjoy a quintessential New England autumn experience by grabbing a little red wagon and leading it out to the pumpkin field. After picking your own gourd, check out the petting zoo, enjoy live music (on the weekends) and try a fresh apple cider donut—or any of the other delicious homemade goods in the Farm Stand. It’s dog-friendly, too!

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Smolak Farms
Photograph: Courtesy Smolak Farms

3. Smolak Farms

Smolak Farms in North Andover has pumpkin picking—and then some. Before getting down to the business and grabbing your own gourd, you can enjoy hop-on hayrides around the farm. Plus, the farm hosts a fall festival for kids every weekend during peak season. Little ones are sure to enjoy cow train rides, a playground, face painting, carnival games and an animal petting area.  For adults, live music and local beer and wine offerings are a popular draw. 

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Prefer to stay inside city limits? Allandale Farm in Brookline doesn’t offer a full picking experience, but the city farm has loads of pumpkins, perfect for pumpkin pie, decorations and of course, for carving into scary Jack-o’-lanterns. They also offer hayrides on Saturdays in October, which is pretty great considering you can get there via the MBTA!

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This Northborough farm promises a whole day of fall family fun with pumpkin picking, a playground, a barnyard and free wagon rides. After a busy day, grab a farm fresh meal from Tougas Grill, or one of the pop-ups the farm is hosting all season, like East Coast Kettle Corn. 

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You’ll get the full fall experience at this South Shore farm, which  offers a day of fun that includes pumpkin picking,  hayrides, a small play area, and picnic tables. There’s also plenty of photo opportunities with the fiery fall colors. Grab a bucket of their hardy mums on your way out, but be sure to hit the bank first because Nihtila is cash only. They’re open weekends starting September 23, through the end of October. Nihtila also offers private tours on weekdays.

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This historic, family-run farm in Framingham grows big, beautiful pumpkins that you can pick right from the patch. There’s also a farm stand with more than 180 varieties of fruits and veggies. Plus, who doesn’t want to get lost in their corn maze?

You’ll find a full range of squash options among this Tyngsboro farm's 14 acres of pumpkins—from mini-pumpkins to gigantic 40-pounders. Parlee Farms also has a farmstand, where you can watch hot apple cider donuts being made before devouring a few while they're still warm. There’s also a stunning sunflower field during the month of September.

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Shelburne Farm in Stow has your standard pumpkin varieties for picking, plus more posh varieties like Cinderella and Ghost. Pick up an ornamental gourd for your fall decor—or grab an edible pumpkin for baking. There’s a farm kitchen serving hot cider donuts, sweet treats and items from the grill. Don’t forget to say hi to the barnyard menagerie.

For 103 years, Westover Orchards has been growing produce at their Harvard home. On fall weekends, a wagon will bring you to their pumpkin patch where you choose your own from their picturesque field. However, there’s laso plenty of pumpkins to choose from at the farm’s store on a weekday. You’ll also find a diverse selection of Westward-grown vegetables in their store, along with local meats, cheeses, eggs, and baked goods. On Sunday afternoons, you can often find a group of bluegrass musicians jamming on the covered porch. Bring your own instrument and join in.

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Just 30 minutes from Boston in the town of Littleton, Pickard Farm is an 150-acre farm with 15 acres dedicated to pumpkins. Bring your own wagon or grab one of theirs as you mosey through the fields to grab one right off the vine. Pickard is also less than a mile from Witch’s Woods in nearby Westford, and only 2 miles from Kimball Farm Ice Cream Stand, which are both perfect for a little spooky season fun. Bonus points: there’s no parking or admission fee.

Boasting one of the best pumpkin selections in the area, Concord’s Verrill Farm is the perfect spot to pick your own pumpkin come September. Be sure to make an online reservation beforehand so you can comb the rows of pumpkins in all shapes and sizes for the ideal jack o’ lantern. Word to the wise: head to the farm store afterward to check out their pies, with a bevy of flavors ranging from Kentucky Bourbon Pecan to classic apple.

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A legacy farm with over 200 years of growing fruit and vegetables, Dowse is located in Metrowest Boston on Route 27 in Sherborn. Starting in September, head to Dowse on weekends to pick your own pumpkin from their rolling acres. If you really want to get in the autumn spirit, check out their  hay bales, corn stalks and hardy mums. Dowse is particularly known for their onsite cider mill, so don’t skip taking a sip at their farm stand after you pick the perfect pumpkin.

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