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I've picked peaches in past years at both Brooksby Farm and Cider Hill Farm. Brooksby Farm is right by the North Shore Mall and very close to 128, and has farm animals, which the kids enjoy.
Cider Hill has a few animals as well, and their cider donuts beat the pants off of Brooksby Farm's. They also offer more than one variety of peach to pick, which I enjoyed. However, it's a bit of a hike, especially from Arlington.
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nashoba valley winery offers pyo peaches.
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It may still be a bit early for good peaches - I think of this month as more blueberry time, but you could check out the following places:
http://www.mass.gov/agr/massgrown/pea...
