New England is a truly idyllic place during autumn, with its chimneys seemingly emitting apple crisp-scented smoke plumes. And the best part? Boston is right at the heart of it all, surrounded by a regional landscape dotted with apple orchards. Apple picking around Boston usually takes up an entire afternoon, filled with all sorts of autumn adventures dreamed up by the orchard folk – from corn mazes and hard cider tastings to deep-fried apple delights, hayrides, petting zoos, pick-your-own sunflowers, and even apple cider slushies. Whether it’s picking your own apples or looking for more ways to enjoy the stunning fall foliage in New England, these orchards are both entertaining and beautiful.
Lookout Farm
Belkin Family Lookout Farm
South Natick, MA
Distance from Boston: 30 minutes
Despite being one of the oldest farms in the country, Lookout Farm still shines with a plentiful supply of the crispiest and sweetest apples around. They’ve kept things modern with The Lookout, an outdoor dining escape offering a menu of craft ciders and beers for a post-pick cool-down, along with their farm market stocked with honey, fruit preserves, fresh-picked fruit, pumpkins, and their signature hard cider.
Connemara House
Topsfield, MA
Distance from Boston: 35 minutes
Part wedding venue, part apple orchard, Connemara House’s lush grounds are simply breathtaking. With over 10 apple varieties, this estate is not just a pretty sight – it could be the perfect spot if you’re hoping to pop the question in a memorable fall meadow.
Dowse Orchards
Sherborn, MA
Distance from Boston: 35 minutes
With more than 50 acres of land and dozens of apple varieties to choose from, Dowse Orchards is a go-to destination for enjoying a fall fruit feast. Filled with all the seasonal favorites, including sweet homemade cider, this roadside farmstand has been operating since 1778. Keep an eye on their Facebook page for updates on apple availability.
Brooksby Farm
Peabody, MA
Distance from Boston: 35 minutes
From squash to pumpkins and, of course, apples, this cozy hideaway has all your seasonal cravings and decorative touches covered. They also offer a Fall Fairytale Trail, hayrides, and campfire s’mores events. Their beloved onsite bakery whips up some of the tastiest treats, including apple cider donuts, whoopie pies, loaf cakes, muffins, monkey bread, and more.
Boston Hill Farm
North Andover, MA
Distance from Boston: 40 minutes
This 12th-generation, family-owned and -operated farm has all the fruit and fall harvest goodies you need, with both apples and pumpkins available for picking. In addition to picking your own treats, the farm stand offers a long list of deli offerings, produce, fresh baked goods (from hand pies to croissants), ice cream, honey, jam, and plenty more to add to your seasonal grocery list. And don’t forget to visit the adorable sheep, goats, chickens, and rabbits.
Connors Farm
Danvers, MA
Distance from Boston: 40 minutes
Connors Farm takes fall activities to the next level with a Putnamville Railroad ride, apple and pumpkin picking, a farm market, a variety of food options, and its iconic corn maze. For the adults, Connors Farm is also home to HYSTERIA, a walking trail that takes you on a terrifying journey through the woods as you encounter some of the farm’s spooky characters. But if you prefer something a bit friendlier, there’s also an after-dark flashlight maze that guarantees no unexpected scares.
Carlson Orchards
Harvard, MA
Distance from Boston: 45 minutes
Carlson Orchards is proud of its premium acreage and is committed to sharing with you what the talented farmers are harvesting and when. For example, do you know which apples are best for pies versus apple sauce? The farm offers an apple variety tutorial to help you plan your apple haul. Grab six-packs of the farm’s locally loved hard ciders, or head to The Cider Barn for a cider-sipping session. Enjoy hard ciders on tap, zero-proof options, Harvard Harvest Slushies, and plenty of food choices.
Smolak Farms
North Andover, MA
Distance from Boston: 45 minutes
For 50 years, this family farm has been one of the most popular fall destinations for New Englanders. While the pick-your-own apples and pumpkins draw in the local crowd, Smolak Farms also has an ice cream stand, bakery, and even an animal area that often steals the show.
Honey Pot Hill Orchards
Stow, VT
Distance from Boston: 50 minutes
Founded in 1926, beloved Honey Pot Hill Orchards has been welcoming visitors to their picturesque farm for years for pick-your-own apples, peaches, blueberries, and other small crops. If you’ve been waiting all year for your favorite variety, you can check the apple ripening schedule. The farm also has hayrides to and from the orchard, a Big Green Monster maze, a hard cider tent, and a petting zoo with goats, rabbits, pigs, and miniature horses.
Russell Orchards
Ipswich, MA
Distance from Boston: 50 minutes
An orchard with its own wine-tasting room? Yes, please! This 120-acre, family-owned and -operated farm is a treasure trove for all things fall. The orchard offers over 20 apple varieties for picking, along with a barnyard, farm store, and bakery. The apple cider donuts are made fresh throughout the day, so be prepared to be greeted by the euphoric scent of fried apple and cinnamon goodness.
Tougas Family Farm
Northborough, MA
Distance from Boston: 50 minutes
With almost every kind of fruit available for pick-your-own, Tougas Family Farm doesn’t disappoint in the DIY fruit-picking department. There’s also a popular barnyard, playground, and farm kitchen to keep you entertained after you’ve picked apples in the fields. Tougas Family Farm goes all out on the autumn vibes with fall-themed ice cream treats, including an Apple Breakfast Sundae featuring a warm apple fritter, cinnamon bun ice cream, fried apples, and caramel.
Carver Hill Orchard
Stow, VT
Distance from Boston: 1 hour
If you want to quickly drive through the countryside on your way to a hidden orchard oasis, consider Stow’s Carver Hill Orchard the perfect backdrop for picking up a bountiful supply of fresh produce. We’re talking about everything from squash, zucchini, late-season blueberries, peaches, and pick-your-own apples. There’s even a snack window with fall-themed treats like apple crisp, sundaes, and apple cider slushies.
Red Apple Farm
Phillipston, MA
Distance from Boston: 1 hour
You may have smelled the delicious apple cider donuts from Red Apple Farm at the Boston Public Market, but now it’s time to visit the source. Not only will you find rows of trees heavy with a variety of different in-season apples, but you can also pick your own sunflowers while you’re there. The farm also has a taproom and restaurant called Brew Barn on site if you’re craving local craft beer and brick-oven pizza.
Woodstock Orchards and Bakery Barn
Woodstock, CT
Distance from Boston: 75 minutes
Take a day trip to the rolling hills of Woodstock and stock up on Mcintosh, Cortland, Empire, Macoun, Jonagold, and over 20 varieties of other apples. The family-run farm offers pick-your-own apples throughout its orchard and a variety of fresh produce in its Apple Barn. The farm also has a Bakery Barn onsite that serves all kinds of homemade sweet treats using the farm’s fresh and seasonal produce. Get some freshly ground peanut butter, maple candy, or just-baked apple turnovers.
Buell’s Orchard
Eastford, CT
Distance from Boston: 75 minutes
This 100-acre, family-owned and operated orchard (established since 1889) has become one of the largest cider producers in Connecticut. Double down on the Autumn nostalgia with pick-your-own apples and pumpkins. Refuel with some warm apple cider donuts after picking versatile apple varieties like Jona-Gold, Cortland, and Mutsu. Looking for a shortcut through the pumpkin patch? Hop on the hay wagon.
