Fall Road Trips from Chicago You’ll Love

17 December, 2025 Sadia Jabeen 3 Comments 1 category

The air becomes crisp, pumpkin spice appears everywhere, and the flat metropolitan landscape of Chicago calls out for a burst of nature’s most colorful display: the wonderful autumn color palette. The best way for Chicagoans to respond to this call is to pack up the car, head to a cider mill, and embark on a fall road trip from Chicago.

The Midwest truly shines in September and October, presenting a rainbow of reds, oranges, and golds that are only a tank of petrol away. Forget the rush of the city for a weekend (or even a day!) and immerse yourself in the natural beauty of the neighboring states. From rugged canyons in Illinois to picturesque lake towns in Michigan, here are 6 of the best, most unforgettable fall road trips from Chicago that promise breathtaking foliage and charming small-town appeal.

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1. Door County, Wisconsin: The Cape Cod of the Midwest (4.5-5 Hour Drive)

Door County, a picturesque peninsula expanding into Lake Michigan and Green Bay, is also sometimes referred to as the “Cape Cod of the Midwest.” In the fall, its maritime beauty is enhanced tenfold by dazzling, burning foliage. The drive up is easy, but once there, you’ll be tempted by stunning possibilities.

The Must-Do Drive: Take the famous Highway 42, which winds beautiful past villages like Fish Creek, Ephraim, and Sister Bay. This route provides spectacular views of the bay with a colorful canopy.
Best Foliage Viewpoint: Peninsula State Park offers the best foliage views. The Eagle Trail offers stunning views of the lake and its colorful islands below. Don’t miss the gorgeous lookout tower for a breathtaking autumn view.
The Vibe: Charming seaside villages, cherry orchards (yes, you can still find products in the fall!), lighthouses, and traditional fish boils. Door County is the quintessential Midwest fall getaway.

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2. Starved Rock State Park, Illinois: A Local Gem (1.5-2 Hour Drive)

You don’t have to cross state lines to enjoy a spectacular display of fall color. Starved Rock State Park, a hidden gem along the Illinois River, is one of the most accessible and impressive fall road excursions from Chicago. The park is known for its impressive sandstone canyons, pure walls, and seasonal waterfalls, which are attractively contrasted by the fiery autumn leaves.

The Must-Do Hike: Follow the trails leading to popular canyons such as St. Louis Canyon and French Canyon. Trails leading through the cliffs and river valley provide the best views of the vibrant colors.
Fall Viewpoint: The Starved Rock Tower, which offers a breathtaking panoramic picture of the Illinois River winding through the raging forest.
Tip for the Road: Visit the adjacent Matthiessen State Park for more canyons and less crowded trails, making your fall road trip from Chicago a double-header of natural beauty.

3. Leelanau Peninsula & Traverse City, Michigan: The Wine Trail Getaway (5-6 Hour Drive)

For a truly immersive long weekend getaway, travel north to Traverse City and the Leelanau Peninsula. This region seamlessly blends natural beauty and refined pleasures, making it a wonderful fall road trip from Chicago for couples or groups. The vineyards, noted for their Riesling wines and cool-climate varieties, turn golden, creating a nearly European vibe.

·       Must-Do Drive: The M-22 Scenic Byway provides breathtaking views of Grand Traverse Bay and Lake Michigan, with rolling hills covered with fiery autumn leaves.
·       Hiking the trails at Sleeping Bear Dunes National Lakeshore offers the best fall views. The climb up the dunes provides breathtaking views of the turquoise lake set against the orange-and-red coastline forest.
·       Local Treat: Stop at one of the many wineries along the Leelanau Peninsula Wine Trail for a tasting with a view.

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4. Galena, Illinois: Historic Charm and Rolling Hills (3-3.5 Hour Drive)

Galena is a charming city that has retained its 19th-century character, making you feel like you’ve stepped back in time. Nestled in the hills of northwest Illinois, its historic architecture, charming Main Street, and surrounding countryside make for a scenic fall getaway from Chicago.

·       A must-see: Stroll along Galena’s historic Main Street, lined with stylish boutiques, art galleries, and restaurants.
·       The ultimate fall spectacle: Enjoy a drive along the winding roads surrounding the city, or visit Horseshoe Mound National Park for panoramic views of the Tri-State region (Illinois, Iowa, and Wisconsin) in full bloom.
·       A must-do: Visit a local apple orchard or vineyard to sample the harvest. Galena’s unique blend of history and nature makes it the perfect destination for a fun and easy weekend getaway.

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5. Brown County State Park, Indiana: The “Little Smokies” (4.5-5 Hour Drive)

If you crave breathtaking, mountain-like scenery, Brown County is the perfect destination. Known as the “Little Smoky” of the American Midwest, this county is home to Indiana’s largest state park and is renowned for its lush, colorful foliage that blankets its rolling hills. This area is one of the most spectacular fall road trips from Chicago, offering a chance to witness the vibrant autumn colors.

·       A Must-Have Drive: Enjoy driving along the scenic roads within the state park, which offer numerous stops and stunning photo opportunities.
·       The Best View of Fall Colors: The observation tower atop the park’s highest point provides a 360-degree panoramic view from 90 feet above the vast forest ablaze with fall hues.
·       Atmosphere: The nearby city of Nashville, Indiana, is a charming, art-themed town, ideal for browsing its unique shops and enjoying a cozy dinner after a long day of hiking.

6. Sagatuck and Holland, Michigan: Art, Dunes, and Fall (2.5-3 Hour Drive)

The neighboring towns of Sagatuck and Holland offer a shorter and more scenic option, combining stunning Lake Michigan shoreline views, a vibrant arts scene, and vibrant forest colors.

·       Must-Have Activity: Climb the 282 steps at Mount Baldehyde Park in Sagatuck for breathtaking views of the Kalamazoo River, Lake Michigan, and the surrounding dunes adorned with fall foliage.
·       Best Fall View: Stroll through Sagatuck Dunes State Park or visit the Windmill Island Gardens in Holland, which look stunning surrounded by autumnal leaves.
·       Sagatuck is an artist haven with its art galleries and trendy boutiques, while Holland offers a touch of Dutch heritage. This autumn road trip from Chicago is an easy and fun trip, perfect for a quick weekend getaway.

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Planning Your Perfect Fall Road Trip from Chicago

To get the most out of your Midwest adventure, plan ahead. Peak color usually occurs from late September through mid-October, though this can vary wildly each year. Monitor regional foliage reports to time your trip perfectly. Whether you choose a short, sweet day trip to Starved Rock or a longer escape to Door County, these fall road trips from Chicago offer a stunning break from the city, proving that the Midwest is a world-class destination for autumn beauty. Which of these breathtaking destinations will be your first stop this fall?

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3 Replies to “Fall Road Trips from Chicago You’ll Love”

rainbow evening says:

January 6, 2026 at 4:18 am

windmill likes in Netherland

Reply
rainbow evening says:

January 6, 2026 at 4:18 am

lovely windmill…. like in Netherland

Reply
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