South of Boston/Plymouth is filled with enticing pick your own (PYO) Farms

PYO Produce: High-bush blueberries and choose-your-own Christmas trees
Season: Blueberry picking in July and August, when berries are ripe, call before coming; hours subject to change.
Hours: For picking, 7 a.m. to 1 p.m.

PYO Produce: Strawberries (June), blueberries (mid-July to August), raspberries (mid-August to September), peaches (mid-July, August), apples (September to October, picking Thursday to Sunday, only), pumpkins (October, from the field on weekends only, from the pile every day).
Hours: PYO is Tuesday through Sunday, 8 a.m. to 4 p.m., by reservation only, made two days in advance. 8-9am is for people ages 60 & older. Retail store is open 9am - 5pm every day.
Also: Farm store sells produce, honey, jarred items, annuals and perennials, vegetable plants; donut barn. Check website for latest information on festivals.