The Best Apple-Picking Trips You Can Take From Boston

We’re on the verge of the most wonderful time of the year in New England -- and what better way to celebrate than to head out for a produce-picking road trip? Pack your favorite fall flannel and hit the road to any of these local farms for prime apple season. It’s sure to be high up on your list of actually fun things to do.

Belkin Family Lookout Farm

South Natick
How far is it: 30-minute drive from Boston
Even though it’s considered one of the oldest farms in the country, Lookout Farm is still kickin’ with a plentiful selection of the crispiest and sweetest apples around. The farm keeps things modern too, with a taproom offering craft ciders and beers for a post apple-picking cooldown. 
Price of a small bag: $14; $17 admission

Dowse Orchards

How far is it: 30-minute drive
With over 50 acres of land and more than 20 varieties of apples to choose from, Dowse Orchards is a go-to if you’re looking to fill up on fresh fruit this fall. Their roadside farmstand, operated for more than 60 years, lets you stock up on all your seasonal favorites including sweet, homemade cider.
Price of a small bag: $16

Brooksby Farm

How far is it: 35-minute drive
Brooksby Farm grows just about every fruit and vegetable you can possibly imagine. From squash to pumpkins to our favorite, apples, this homey haven has all of your seasonal cravings. The famous bakery also whips up some of the tastiest baked goods around, featuring apple cider donuts, muffins, and monkey bread. 
Price of a small bag: $10

Boston Hill Farm

North Andover
How far is it: 35-minute drive
This 12-generation, family-owned and operated farm holds fall festivals every weekend beginning Sunday, September 15, through the end of October. Festivals include live music, a petting zoo, and no shortage of apple and pumpkin picking. Another perk? The farm is dog-friendly so there’s no need to leave anybody behind -- just make sure to bring a leash. 
Price of a small bag: $20

Connors Farm

How far is it: 40-minute drive
For maximum fall activities, head to Connors Farm for autumn-inspired attractions and prime apple picking views. If you’re down for a challenge, try the flashlight maze any Friday or Saturday night in October or Halloween night -- which falls on a Thursday this year.
Price of a small bag: $11, $10 admission on weekdays and $15 on weekends

Shelburne Farm

How far is it: 45-minute drive
If you’re looking for something outside of the standard Red Delicious and McIntosh, Shelburne Farm grows more than 80 different kinds of apples. If that isn’t tough enough of a decision, the farm’s Apple Shop, housed in an antique 19th-Century barn, has a selection of homemade goods from cider donuts to fudge for you to contemplate devouring.
Price of a small bag: $20

Smolak Farms

North Andover
How far is it: 45-minute drive
Smolak Farms is yet another ideal destination for avid apple pickers. Something to keep in mind for next year, the annual Whim Dinner Series. It’s a lantern-lit, farm-to-table dinner prepared by notable New England chefs -- with the weekly series closing out on August 28, featuring Chef Stephen Coe of Matadora. If you’re disappointed you’re missing out, there are a whole herd of animals (including alpacas) at the farm to cheer you up during the rest of the season.
Price of a small bag: $20

Westward Orchards

How far is it: 45-minute drive
Celebrating its 100th harvest this year, Westward Orchards offers a wide pick-your-own-fruit selection against a picturesque backdrop. The orchard puts local farms first through its community support and both homegrown and locally produced items. What’s not to love? 
Price of a small bag: $19

Nashoba Winery

How far is it: 1-hour & 10-minute drive
For this weekend excursion, be sure to enlist in the help of a designated driver. Nashoba Winery offers both apple picking and daily wine tastings. Enjoy stunning views at the property’s J’s Restaurant and outdoor patio -- because we all deserve to treat ourselves from time to time. Your DD will have their day.
Price of a small bag: $20

Carlson Orchards

How far is it: 45-minute drive
Carlson Orchards takes pride in its premium orchard -- and filling everyone in on what exactly they’re picking. To better educate yourself on apples, Carlson Orchards takes you through its varieties with descriptions on the farm’s website. What’s best for a pie? No need to guess because this place has you covered. There’s also a six-pack of its famous hard cider, Oak Hill Blend, calling your name.
Price of a small bag: $20

Honey Pot Hill Orchards

How far is it: 50-minute drive
The beloved Honey Pot Hill Orchards has all of your fall favorites wrapped into one special. For $18 per person, enjoy the farm’s fun pack, which includes a picking bag, hayride, cider donut, candy apple, hayride, apple cider guzzler, and entrance to the farm’s little hedge maze. We recommend the investment for your next family-fun outing.
Price of a small bag: $20

Russell Orchards

How far is it: 50-minute drive
This 120-acre, family-owned and operated farm is a one-stop-shop for all things fall. Between the 10 varieties of apples available for picking and the barnyard, bakery, produce store, and wine tasting room, Russell Orchards provides something for everyone in your group.
Price of a small bag: $20; $4 admission

Parlee Farms

How far is it: 50-minute drive
This pick-your-own-farm not only has a wide variety of apples to choose from, but an option to cut your own flowers through late September. Another plus to making the trip out? The farm’s Mary’s Country Kitchen and Bakery serves up homemade baked goods. A bag of donuts and fresh cut flowers? That’s one way to win someone’s heart.
Price of a small bag: $25

Red Apple Farm

How far is it: 1-hour drive  
You’ve probably caught a whiff of Red Apple Farm’s apple cider donuts at the Boston Public Market, but now’s the time to take a trip to the source. With walking trails, farm animals, hay rides, and, of course, those fresh apple cider donuts, you’ll feel confident in your decision to drive out this weekend -- and maybe the next.
Price of a small bag: $22

Still can't get enough? Check out our guides to the best apple picking and orchards to visit in New York and New Jersey.

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Jillian Hammell is a contributing writer, with an endless list of fall activities in her que. Follow her on Twitter and Instagram