Chicago

The Most Beautiful Fall Foliage within Driving Distance of Chicago

Let the leaf-peeping commence.

Tonya Kay/Shutterstock
Tonya Kay/Shutterstock
Tonya Kay/Shutterstock

As a wise hippie once said, “To everything, there is a season.” And that season, believe it or not, is already fall. Celebrate the earth’s resilient compulsion to keep on spinning despite all of our young decade’s peaks and valleys (OK, maybe just endless valleys) by scoping out the absolute best places to peep the leaves as they’re turn-turn-turning away. So take a break from stomping around the pumpkin patch and get in one last blast of glorious nature before Old Man Winter rears his ugly head. Here’s everywhere to see the Midwest’s breathtaking foliage bounty this fall.

Danita Delimont/Shutterstock
Danita Delimont/Shutterstock
Danita Delimont/Shutterstock

Illinois

Peaks mid- to late-October
Iconic: Perched on the southernmost tip of Illinois, Shawnee National Forest is well worth the journey for questing leaf peepers. The nature-lover’s destination is home to nearly 300,000 acres of lush oak and hickory trees, miles of sweeping hills, towering bluffs, and, most importantly, the Garden of the Gods, a 320-million-year-old collection of gargantuan sandstone formations and craggy cliffs offering epic technicolor views of the dense autumnal landscape below. For the ultimate vantage point, lace up your hiking boots and set off on the quarter-mile Observation Trail, a winding sandstone path that opens up onto one of the state’s most photographed panoramas. Take note of the interpretive signs posted along the way to gain insight into the area’s fascinating geological history.

Nejdet Duzen/Shutterstock
Nejdet Duzen/Shutterstock
Nejdet Duzen/Shutterstock

Lesser known: If small town charm is more your style, point your GPS in the direction of Galena, one of Northern Illinois’ most picturesque fall escapes. Amid the quaint shops, farm-to-table restaurants, intriguing historic sites, and top-notch wineries and distilleries, you’ll find Horseshoe Mound Preserve, a 1063-foot scenic outlook providing 360-degree views of the Mississippi River in all its colorful glory. If the weather cooperates, sights can stretch upwards of 50 miles in any direction and span a confluence of three different states. The park is accessible on foot via a handful of groomed, occasionally steep hiking trails or by driving up a short dirt road to the tippity-top and taking it all in from the comfort of your car.

The Morton Arboretum
The Morton Arboretum
The Morton Arboretum

Close to home: Those not wanting to leave Chicagoland for their foliage fix can chart a quick course to the 1,700-acre “tree museum” that is Lisle’s Morton Arboretum. Cruise through both the East and West Sides of the park, and be sure to get out and stretch your legs along the many chipped or paved trails and gentle mowed paths. We’re partial to the area around the West Side’s Lake Marmo, but wherever you go, you’ll be treated to the finest assemblage of fall scenery within many, many miles. This place ain’t exactly a secret, however, so schedule your visit mid-week or get ready to wait in line on the weekends. And to keep things safe, timed entry advance reservations are required for the time being.

Aeypix/Shutterstock
Aeypix/Shutterstock
Aeypix/Shutterstock

Indiana

Peaks mid- to late-October
Iconic: Ask any tried and true Hoosier the state’s best spot for autumnal gaping and they won’t hesitate to send you straight to Brown County State Park. The massiv-we’re talking upwards of 16,000 acres massive-pastoral mashup of undulating hills, broad vistas, and hidden gulches sits just outside of the equally delightful college town of Bloomington (pro tip: Upland Brewpub has your post-excursion nachos and barrel-aged beer needs covered). A paved 20-mile road traversing the richly forested environment invites hoards of drivers to soak up the scenery with minimal effort while a dozen hiking trails ranging from rough and rugged to easy and breezy provide adequate leg-stretching opportunities. Don’t leave without snapping a requisite selfie atop the park’s famous 90 foot Fire Tower.

Hank Erdmann/Shutterstock
Hank Erdmann/Shutterstock
Hank Erdmann/Shutterstock

Lesser known: For a more secluded leaf-viewing experience, hop off the beaten path and make a beeline 80 miles northwest of Indianapolis to Portland Arch Nature Preserve. Perched on the bank of the Wabash river, the 430-acre refuge is chock full of hickory, black gum, and sugar maple trees, creating a fiery inferno of vivid scarlet, gold, tangerine, and rusty brown hues that lasts deep into the season. The sandstone gorge, trickling creek, and eponymous natural rock bridge yield ample photo-ops, broken up by sundrenched prairies and dramatic cliff sides. Finish the day with a quick trip up to nearby Williamsport Falls, the state’s tallest waterfall, and dip your tired toes into the cool, refreshing waters.

Hank Erdmann/Shutterstock
Hank Erdmann/Shutterstock
Hank Erdmann/Shutterstock

Close to home: Many locals think of Indiana Dunes National Park as strictly a summer destination, but the park’s 15 miles of breezy Lake Michigan shoreline have plenty of appeal for fall spectators as well. With significantly fewer crowds and more room to maneuver, venture beyond the beach and get lost in the park’s 50 miles of trails, listening to the sound of the wind rush between the color-soaked trees at serene local spots like Miller Woods. The more exercise-challenged car-bound among us can also get a glimpse of the seasonal glory by cruising along Highway 12 or The Dunes and Lake Drive. And the best part? You’ll be back home in time to catch the new episode of Succession.

Boundless Images/Shutterstock
Boundless Images/Shutterstock
Boundless Images/Shutterstock

Michigan

Peaks mid-September to late-October
Iconic: The Mitten State is rife with natural wonders, sure, but Emmet County’s Tunnel of Trees is hands-down the most breathtaking way to immerse yourself in fall’s radiant splendor. The tree-lined 20-mile stretch of Route M-119 runs along Lake Michigan’s sandy shore from Harbor Springs to Sturgeon Bay, blanketing drivers in a sea of eye-catching color and crisp autumn air. And if 20 miles seems like too short a ride, don’t worry-there are plenty of excuses to stop along the way, including sand dune-strewn beaches, nature preserves with groomed hiking trails, century-old family farms, roadside stands, general stores, historic and architectural finds, and other curiosities worthy of a full day’s exploration.

SNEHIT PHOTO/Shutterstock
SNEHIT PHOTO/Shutterstock
SNEHIT PHOTO/Shutterstock

Lesser known: If the Tunnel’s congestion potential has you sweating, avoid the caravans and travel instead to the Keweenaw Peninsula where Brockway Mountain Drive presents an explosive nine-mile tour of the UP in all its shimmering exquisiteness. Start by rolling up to Brockway Mountain Lookout for a spectacular perspective of Lake Superior’s ice blue waters, then make your way down to Brockway Mountain Wildlife Sanctuary and keep your eyes peeled for Bald Eagles soaring high above the thick, jungle-like canopy of flamboyantly colored trees. Make sure to hit up Manganese Falls for a brief wade into the frothy life-giving pools before winding down the day by picking up a locally brewed sixer from Brickside Brewery and watching the mighty sun set over the historic Copper Harbor Lighthouse.

David A Yohnka/Shutterstock
David A Yohnka/Shutterstock
David A Yohnka/Shutterstock

Close to home: The Red Arrow Highway, stretching across a laid-back 21 miles of scenic Southwest Michigan coastline just across the Indiana border, is many things to many people: a beachfront hideaway, a boozy brewery and distillery tasting route, an easy escape when you just want to get the hell out of dodge. It’s also a more than worthy candidate for your foliage peeping excursion, stopping off at state parks like Warren Dunes and Grand Mere for dazzling colors after getting your fill of some excellent fall offerings in bottle form at nearby Journeyman Distillery and Tabor Hill Winery (apple cider is for quitters). On second thought-maybe take an Uber for this one.

Samloganphotography/Shutterstock
Samloganphotography/Shutterstock
Samloganphotography/Shutterstock

Wisconsin

Peaks mid-September to mid-October
Iconic: Buckle up and cruise over to Door County’s absurdly spectacular Coastal Byway for 66 full miles of leaf-peeping bliss. Highways 42 and 57 combine to lead travelers on a loop all the way from Sturgeon Bay to Gills Rock at the peninsula’s windswept northernmost tip, set to a backdrop of Lake Michigan’s crashing waves to the east and the calming waters of Green Bay due west. A diverse array of well-maintained state parks like Potawatomi, Newport, and Whitefish Dune add to the area’s fairytale appeal, as do historic lighthouses, u-pick apple farms, mom-and-pop cafes, and, of course, more awe-inspiring fall foliage than just about anywhere else on God’s scorching orange earth.

Jose Lejin P J/Shutterstock
Jose Lejin P J/Shutterstock
Jose Lejin P J/Shutterstock

Lesser known: A cluster of heavily wooded hills centered around a stunning 360-acre cobalt blue lake, Devil’s Lake State Park is one of the Badger State’s most cherished natural getaways-and, thankfully, it’s only about an hour’s drive from Madison. If all those bluffs and beaches aren’t enough to stoke your fall fire, keep the party going by exploring some of the surrounding leaf peeping-hubs like Gibraltar Rock County Park, known for its super steep peak and astounding views just across Lake Wisconsin, or jump over to the Merrimac Segment of the Ice Age Trail for some lowland adventuring.

Thomas Barrat/Shutterstock
Thomas Barrat/Shutterstock
Thomas Barrat/Shutterstock

Close to home: Locals know Lake Geneva can be an absolute zoo in the summer, but fall is a whole other animal. A miniature Door County-style experience awaits nature-seekers who steer clear of the still-bustling downtown in favor of lesser visited haunts like Bigfoot Beach State Park and Rustic Road 29. South Lake Shore Drive is an excellent foliage-packed alternative route between downtown Lake Geneva and the popular Abbey Resort, but pretty much nothing beats a sunny fall meander along the show-stopping 26-mile Geneva Lake Shore Path, extending across the length of the entire lake. Well, maybe a sunny summer day meander-but who’s keeping score?Want more Thrillist? Follow us on InstagramTwitterPinterestYouTubeTikTok, and Snapchat.

Meredith Heil is a Senior Cities Editor at Thrillist.

Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington PostThe GuardianCNN TravelChicago TribuneLonely PlanetVICEOutside Magazine and more. Follow @thejaygentile.

Chicago

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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