Travel

The Most Beautiful Fall Foliage within Driving Distance of Chicago

As socially distant as fun gets.

Brown County State Park
Brown County State Park | Rain0975 / flickr
Brown County State Park | Rain0975 / flickr

As a wise hippie once said, “To everything, there is a season.” And that season, believe it or not, is about to be fall. Celebrate the earth’s resilient compulsion to keep on spinning despite all of 2020’s peaks and valleys (OK, maybe just endless valleys) by scoping out the absolute best places to catch the leaves as they're turn-turn-turning away.

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.

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 and its colorful bounty. 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.

Brown County State Park
Brown County State Park | Dorothy Riley / Unsplash

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 massive -- 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.

Lesser known: For a more secluded leaf-viewing experience, hop off the beaten path and make a bee-line 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.

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, and general stores, historic and architectural finds, and other curiosities worthy of a full day’s exploration. 

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 glory. Start by rolling up to Brockway Mountain Lookout for a spectacular perspective on 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.

Devil's Lake State Park
Devil's Lake State Park | zenia / flickr

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.  
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. 

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.