This North Shore farm includes a farm store, open daily; a hard cider bar, dessert bar, and food truck on weekends; some play options for kids; a bee observatory; a barnyard with chickens; and a variety of family-friendly events. Depending on the time of year, pick-your-own apples, peaches, and/or various berries may be available; check the website for updates. Mid-October is all about apples — around a dozen different varieties — and picking is generally available daily, although there may be pauses to allow fruit to ripen. Reservations are accepted two or three days ahead of time, depending on conditions, but walk-ins are welcome. Picking is available rain or shine.

Parlee Farms offers a robust pick-your-own schedule, usually starting around mid-June with strawberries and ending around late October with pumpkins and apples, with cherries, blueberries, and more in the middle. The 2021 season will tentatively end on October 24, but watch the website for updates. Hayrides are available some days; when they’re not, it’s a five-to-eight-minute walk to the orchard. Parlee Farms also has a farm stand, bakery, hay maze (closed for the 2021 season), tractor rides for kids (closed for the 2021 season), and farm animals to pet and feed.

The pick-your-own schedule at Andover’s Smolak Farms typically runs from around mid-June (strawberries) to Christmas (Christmas trees), with raspberries, blueberries, cherries, pumpkins, and more also on the roster in between. Facebook and the farm’s mailing list are the best places to get up-to-date pick-your-own information, rather than the farm’s website. Smolak’s bakery and farm stand are open daily, and there’s ice cream, too, available at its own stand in the summer and early fall and at the farm stand the rest of the year. There’s also playground and barnyard space, with animals including alpacas, pigs, fallow deer, and more. Check out the night hayride options, which include the opportunity to gather around a campfire and make s’mores.

This family farm — around for an astounding 12 generations — is one of the only dog-friendly spots on the list (leashes required, and dogs can’t go inside the farm stand). No reservations are currently needed for pick-your-own activities, which usually go until late October. Peaches, apples, and pumpkins are available in the fall, with strawberries, blueberries, and raspberries available earlier in the year. Find updates on the farm’s website.

Bostonians can find a Red Apple Farm stand — complete with mini cider doughnuts and lots of fudge — right within city limits, at Boston Public Market. But for pick-your-own apples and more, head out to Phillipston, which includes a farm store and a seasonal “brew barn” full of beer, cider, barbecue, and live music. The pick-your-own schedule for apples runs from late July to late October or early November, but there are other items available, too, including pumpkins, (dig-your-own) potatoes, popping corn, and more throughout October, with the potatoes stretching into November. Find weekly picking condition updates here.

Pick-your-own apple season is currently underway in October 2021, operating daily; watch for berries, peaches, nectarines, and more at other times of year, starting with blueberries around early July. After picking, head into the cider barn taproom for hard cider (and cider-based cocktails), sweet cider, and pizza.

Open daily for apple and pumpkin picking in the fall, Shelburne Farm also offers cider doughnuts, playground space, barnyard animal visits, hay rides, food trucks, and live music. Apple lovers will enjoy the huge variety available — over two dozen different apples as of mid-October 2021. Find an approximate picking schedule here, and find daily updates here.

Carver Hill’s pick-your-own season runs from July through October, with pumpkins, peaches, apples, tomatoes, cherries, beans, eggplant, corn, and more available at various times throughout the season. Customers are welcome to bring their own picnic to eat in the orchard, and the farm’s concession stand also offers hot dogs and some snacks.

This fifth-generation Framingham farm features pick-your-own berries, pumpkins, and flowers, depending on the season; pumpkin picking generally goes into November. There’s also a fall corn maze, a haunted hayride in October, and a very photogenic sunflower field. The farm stand is open from May through November; watch for cider doughnut sundaes. Don’t forget to visit the horses, sheep, chickens, and turkey.

The South Natick farm — and brewery, cidery, restaurant, and farm market — offers seasonal fruit picking as well as onsite dining and drinking (outdoors in the summer and fall, under greenhouse cover in the late fall and early winter). Current pick-your-own hours are daily except for Monday, from 10 a.m. until 5 p.m. Online reservations for picking are available but not required, although depending on the day, it might save you a few bucks; Lookout does recommend making dining reservations ahead of time, especially for weekends. Check the website ahead of time to see what varieties of apples (and/or other fruits, like peaches and pears) are available each day. Note that several parts of the pick-your-own experience are closed for the 2021 season, including the train and the barnyard play area.

Pakeen Farm has a bit of a limited schedule compared to other farms on this map; go there Thursday through Sunday during fall 2021, but note that some pre-pandemic activities are currently on pause, such as the cow train, mini maze, and farm animal viewing. There’s also no apple picking this year. There is, however, pumpkin picking running until around October, not to mention cider doughnuts. From Black Friday through mid-December, there are choose-and-cut Christmas trees (and more cider doughnuts). Find updates online.