The Best Apple-Picking Trips You Can Take From Chicago

A little taste of normalcy.

All Seasons orchard
Courtesy of All Seasons Orchard

2020 has been quite the doozy. Professional athletes are trapped in bubbles, the beaches are closed, we haven’t shaken a stranger’s hand in months, an actual tornado touched down in Roger’s Park, and a trip to the grocery store requires a full beekeeper get-up. But if there’s one thing we can rely on, it’s that the seasons will continue to change, and when they do, the trees will fruit once again. So grab your best mask, respect social distance protocols, and celebrate this tiny, meager taste of normalcy this autumn by visiting one of these outstanding pick-your-own apple orchards, each located within driving distance of our fair city.

Honey Hill Orchard

Waterman, Illinois
How far is it: 90-minute drive
This pastoral Dekalb County destination is chock full with seasonal attractions, tasty treats like pies and cider donuts, and, of course, plenty of farm-fresh apples. Depending on the time of year, visitors can (literally) pick from 25 different varieties including coveted heirlooms like winesap and cortland. The quaint country store, wagon rides, and picturesque 1880’s converted apple barn only add to the charm. Check out the harvest schedule to keep tabs on what deliciousness awaits.
Price of a small bag: $9.50

Apple Holler

Sturtevant, Wisconsin
How far is it: 75-minute drive
This sprawling fruit-filled oasis sits just over the Wisconsin border near Racine and is well worth the trek up to cheesehead territory. Lush apple and peach trees dot the verdant landscape, offering pickers an incentive to load up from early July through late October (peep the full bounty, including 30+ apple varieties, here). If you venture up, make sure to clear your calendar for the day -- it’s all but impossible to resist a restorative, post-picking nature walk through the 78-acre orchard and hardwood forest.
Price of a small bag: $15

Royal Oak Farm
Royal Oak Farm | Courtesy of Blue Chair Stories

Royal Oak Farm

Harvard, Illinois
How far is it: 95-minute drive
Lose yourself in the country’s only apple tree maze, a breezy one and a half mile stretch of trails bursting with nine varieties of u-pick apples, a climbing tower, games, and other open-air curiosities. Afterward, hit the Country Kitchen’s sunny porch for some good old fashioned home cooking (chicken pot pie, homemade egg salad sandwiches, Chicago dogs) but make sure to save room for the ideal sugary finish: a square of fresh, velvety fudge and a ooey-gooey hand-dipped caramel apple. 
Price of a small bag: $13

County Line Orchard

Hobart, Indiana
How far is it: 60-minute drive
Indiana might not be the first Midwestern state that leaps to mind when planning an apple picking adventure but this inviting 40-acre expanse has been out here proving naysayers wrong for years. Stuff your bag with 25 different mouthwatering varieties, ripening between early September and late October, then settle in for a socially distanced outdoor picnic complete with pulled pork, juicy brats, and a refreshing cider slushie to wash it all down. Afterwards, work off your lunch with a mind boggling trip through the corn maze or feed your inner hippie with a stroll through the overgrown sunflower patch.
Price of a small bag: $1.79/pound

Jonamac Orchard

Malta, Illinois
How far is it: 75-minute drive
Head due west out of Chicago and a little over an hour later you’ll pull up on this 105-acre family-owned beauty, home to over 20,000 blossoming apple trees and 30+ apple varieties plus a corn maze and bustling cider house (yes, that means there’s hard stuff, too). Grab a sixer of bright, effervescent and JonaSMACK dry hopped cider to fuel your apple-hunting expedition and set out to discover mother nature’s riches. Looking for something in particular? Sign up for text alerts on Jonamac’s markedly impressive website and they’ll ping you whenever your prized fruit is ripe for the picking.
Price of a small bag: $15

Kuipers Family Farm

Maple Park, Illinois
How far is it: 65-minute drive
Pumpkins, sunflowers, Christmas trees, and, most importantly, apples abound at Wade and Kim Kuipers’s year-round family-friendly fun fest, stationed just a stone’s throw from Chicago’s western suburbs. Over a dozen varieties of the beloved autumnal cruncher takes center stage from mid-August until late-October and availability is updated weekly via a handy hotline (815-827-5200 Ext. 1). An onsite eatery provides sustenance in the form of hot dogs, burgers, sandwiches, and the like while the orchard’s bakery beckons visitors with a steady stream of cider donuts, fruit pies, caramel apples, homemade fudge, and more. Come hungry.
Price of a small bag: $10.99

All Seasons Orchard  donut machine
Courtesy of All Seasons Orchard

All Seasons Orchard

Woodstock, Illinois
How far is it: 70-minute drive
Upwards of 15,000 fruit trees, heavy with different types of shiny apples and luscious pears from late August to mid-October, welcome fall day-trippers to this upbeat Woodstock escape. All that picking got you hungry? The Country Kitchen has your pulled pork sandwich and cheeseburger needs covered and for a quick fix, a concession stand hawks kettle corn, donuts, and sweet apple cider slushie. Cornhole boards, giant mazes, a petting zoo, and a 10-acre pumpkin patch are on hand to keep things interesting.
Price of a small bag: $14

Stade's Farm & Market

McHenry, Illinois
How far is it: 80-minute drive
There’s much more to this pastoral northwestern Illinois favorite than apples. Depending on the season, enterprising pickers can diversify their load here by piling on a whole slew of other freshly harvested produce from raspberries and strawberries to pumpkins, tomatoes, and sugar snap peas. Throw in an entire “Farmtractions” theme park -- carousel, kiddie train, water wheel, tractor lift, swing ride, corn maze, and tons more -- and you’ve got yourself one heck of a Saturday afternoon. Pro tip: Follow Stade’s on Facebook for the latest on what’s popping.
Price of a small bag: $10

Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.

Meredith Heil is a contributor for Thrillist.