Fall in the midwest will quickly banish any notion that the region’s topography makes for boring drives. A day trip from Chicago holds a world of possibilities, from covered bridges to lakeshore views — all enhanced by the blazing colors of fall. Waterfalls, marshes, harvest fields, and more provide entrancing backdrops for the best photos of the season.
Red Arrow Highway
Drive around Lake Michigan’s shoreline for miles of roads lined by exploding fall foliage, plus beach access so you can see double with red, orange, and yellow trees reflected in the brilliant blue water. Galien River County Park offers one of the best autumn vistas — cross the 300-foot Canopy Walk to the 60-foot Marsh Overlook Tower for a prime photo spot with a backdrop of brilliant fall colors.
Illinois River Road
Want your fall colors with a side of waterfalls? Take the Illinois River Road — a national scenic byway offering a breathtaking array of fall foliage — to Starved Rock State Park for a unique vantage point on autumn’s best displays. Tumbling waterfalls embraced by halos of orange and yellow leaves are practically begging to be photographed, while rock formations provide natural frames for the mustard- and ochre-colored foliage. Tough to beat.
Shawnee Hills Wine Trail
You’ll need a DD for this one, but it’s worth it. Dotted with wineries in tiny towns, the Shawnee Hills Wine Trail offers plenty of comparison points for the crimson of cabernet vs. falling leaves. Head south from Chicago to wind through the tree-lined two-lane road punctuated by the epitome of Midwestern small towns. The vineyards (and their fruits) are an added visual and gustatory bonus.
Parke County, Indiana
A southeast drive will take you to Indiana’s Parke County, which boasts over 30 covered bridges — especially aesthetically pleasing when bordered by fall colors. Harvest fields fill the gaps between bridges, offering more quintessentially fall photo ops. If you want to really go all in, time your trip to coincide with the Covered Bridge Festival in Rockville, where you can peruse craft vendors and take home some homemade apple butter from a Quaker community.
Door County Coastal Byway, Wisconsin
Encompassing some of the best of this iconic Wisconsin fall destination, the Door County Coastal Byway includes 66 miles of curving roads with seemingly endless stretches of colorful trees on either side. The towns dotting the route call to mind New England clapboard and steeples, offset by the most Instagrammable fall colors. If you want to extend your drive, continue on the zigzagging Route 42 for more fiery fall color views.