Best Strawberry Picking in Boston and Summer Strawberry Festivals

Hollis Hill Farms photo courtesy of the Massachusetts Office of Travel and Tourism
Hollis Hill Farms photo courtesy of the Massachusetts Office of Travel and Tourism
5/12/24 - By Kelley Heyworth

Strawberry season is here, and that means it’s time to grab a bucket, round up the kids, and head to the fields! Sweet, juicy, and just the right size for little hands, strawberries are one of the most fun fruits to pick—and luckily, there are plenty of berry-filled patches near Boston ready for the picking. Whether they end up in a pie, a smoothie, or straight into mouths on the ride home, strawberries never last long once they leave the field.

We’ve gathered the best pick-your-own strawberry spots near Boston to help kick off the season. Just don’t forget to call ahead—some farms are still gearing up for the season, and berry availability can change faster than a toddler’s mood.

And when strawberry season winds down, be sure to check back with our Farm and Pick-Your-Own Guide for Boston Families for more fruity adventures, farm-fresh ice cream, and outdoor fun. Our Boston Summer Fun Guide has you covered for even more ideas to fill those long sunny days!

Make sure to check each farm's site before heading out to see if there are requirements for reservations or changes in hours of operation.. 

This post was originally published in June 2020; updated May 2025.

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About the Author

Kelley Heyworth
Kelley Heyworth is the regional editor for Mommy Poppins, covering Boston, Connecticut, and the rest of New England. She has covered parenting and health topics for nearly two decades, as an editor for Child Magazine and Fitness Magazines and a contributor to Parents Magazine, Mommy Nearest, and other national publications and websites. Previously, she was a writer and editor at Sports Illustrated and Philadelphia Magazines. A mom of three boys outside of Boston, Kelley also writes a blog, Happy Healthy Kids, and loves hiking, running, cooking, gardening, and spending time at beaches in Nantucket, Connecticut, and New Jersey with family and friends.