The Best Apple-Picking Trips You Can Take From Chicago

An apple a day keeps the winter at bay…

Edwards Apple Orchard
Edwards Apple Orchard
Edwards Apple Orchard

This time last year, many of us weren’t too thrilled that summer was coming to a close, leaving the sweater box hidden beneath the bed well into the winter months as an act of collective resistance. And who could blame us? This year, however, keeping up with the calendar hasn’t been much easier, but nature’s clock keeps on tickin’, and harvest time is upon us once again. Year-round outdoor activities remain a global godsend, so dust off your boots, kiss your Crocs goodbye, and enjoy one of autumn’s staple events: good old-fashioned apple-picking.

While you’re at it, no orchard sojourn is complete without indulging in some apple cider donuts, apple cider, apple fritters, apple compote, apple pie, apple butter, apple wine, apple brandy… you get the picture. Thankfully, these standout area farms have you covered on all things apple, in addition to non-apple offerings like petting zoos, tricky corn mazes, and more. Press pause on your work-from-home routine for a day and head out to one of these top pick-your-own palaces, all located a short drive from Sweet Home Chicago.

Door Creek Orchard
Door Creek Orchard
Door Creek Orchard

Door Creek

Cottage Grove, Wisconsin
How far is it: 2.5 hour-drive
Making the trek out to the Dairy state will be worth it as soon as you catch sight of this quaint orchard’s vast selection of modern and heirloom varieties. That’s 90 different types of apples to be exact, and you’d be hard-pressed to find that much diversity elsewhere. Although small, this delightful farm is extremely meticulous about integrating sustainability practices, including beehives for pollination and rare Chocolate Welsh Mountain Sheep for keeping the soil rich and fertile. After you get your picking fix, take a moment to soak up the scenery by meandering through the rolling fields, serene prairie, and lush woodlands. Also, check out their fellow orchardist Eliza Greenmans’s ugly apple blog if you want to educate yourself on the wonders of blemished fruit.
Cost: Admission is free; U-pick starts at ~$12 per 1/2 peck bag

Edwards Apple Orchard

Poplar Grove, Illinois
How far is it: 90-minute drive
Along with 50,000 apple trees, this family-run and environmentally conscious operation also grows raspberries and pumpkins (u-pick available), and has been perfecting their stellar apple cider donut recipe over the last 30 years. After you’ve picked your bounty of autumn beauties and ginger golds, head over to the Cider Cellar for pulled pork sandwiches and sweet treats like homemade fudge and warm apple pie. They also hawk a variety of specialty food items like spicy jams and sweet salsas.
Cost: Admission is free; U-pick prices vary

Goebbert's Farm - Pingree Grove
Goebbert’s Farm – Pingree Grove
Goebbert’s Farm – Pingree Grove

Goebbert’s Pumpkin Patch & Apple Orchard

Pine Grove, Illinois
How far is it: 70-minute drive
This lively all-season farm thinks of everything when it comes to providing an eclectic and exciting harvest experience, with pig races, pumpkins slides, magic shows, and a carousel. Oh-and singing chickens (?). All the perks, including apple picking, of course, are included in their Fall Festival price. In addition to the curious list of attractions, the Farm Stand provides a cornucopia of autumn’s best, including crunchy green beans, squash, and sun-ripened berries.
Cost: Admission runs $17 – $20 per person; U-pick prices vary

Honey Hill Orchard

Waterman, Illinois
How far is it: 90-minute drive
This pastoral Dekalb County destination is chock full of 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 charming country store, wagon rides, and picturesque 1880’s converted apple barn only add to the allure. Check out the harvest schedule to keep tabs on what deliciousness awaits.
Cost: Admission is free; U-pick runs $9 per 1/4 peck bag

Apple Holler
Apple Holler
Apple Holler

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 drive 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-pick nature walk through the 78-acre orchard and hardwood forest.
Cost: Admission is free; U-pick runs $15 per 1/4 peck bag

Photo courtesy of Goebbert's Pumpkin Patch & Apple Orchard
Photo courtesy of Goebbert’s Pumpkin Patch & Apple Orchard
Photo courtesy of Goebbert’s Pumpkin Patch & Apple Orchard

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 (AKA chicken pot pies, homemade egg salad sandwiches, Chicago dogs) and make sure to save room for the ideal sugary finish: a square of fresh, velvety fudge and an ooey-gooey hand-dipped caramel apple.
Cost: Admission runs $10 per person (includes 1/4 peck bag)

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 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.
Cost: Weekday admission is free ($6 per person on weekends and holidays); U-pick runs $15 per 1/2 peck bag

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 with a steady stream of cider donuts, fruit pies, caramel apples, homemade fudge, and more. Come hungry.
Cost: Admission runs $12.99 per person (includes 1/4 peck bag)

All Seasons Apple Orchard
All Seasons Apple Orchard
All Seasons Apple 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 your stomach grumbling? The Country Kitchen has your chicken tenders and cheeseburger needs covered and for a quick fix, a concession stand hawks kettle corn, donuts, and sweet apple cider slushies. Cornhole boards, giant mazes, a petting zoo, and a 10-acre pumpkin patch are on hand to keep things interesting.
Cost: Admission starts at $11 per person (includes 1/4 peck bag)

Stade’s Farm & Market

McHenry, Illinois
How far is it: 80-minute drive
There’s much more to this northwestern Illinois favorite than apples. Depending on the season, enterprising pickers can diversify their loads 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 so much 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.
Cost: Admission starts at $10 per person (includes 1/4 peck bag)

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Meredith Heil is a Senior Cities Editor at Thrillist.

Elanor Bock is a contributor for Thrillist.


Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or…

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions…I think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary is a drinks expert and writer. His first cocktail book, Drink What You Want, is available now, and his next book, Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.


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