It’s autumn, and if you live in the Midwest, that means you can breathe in the crisp air, smell the burning leaves, and satisfy your aching desire to go to an apple orchard. Here’s the plan: take off a week or two and follow this Autumn Midwest road trip to cross off all your seasonal activities at once.

Since our road trip is in the general shape of a circle, this itinerary can begin at any stop. Simply go to the top of the list once you finish. For now, let’s start with ...

Weston’s Antique Apple Orchard, New Berlin, WI

For many Midwesterners, visiting an apple orchard is the quintessential autumn activity, and Weston’s is one of the region’s best, with more than 100 apple varieties and hilltop views of the surrounding countryside. Sample one of Weston’s heirloom apples, such as calville blanc d'hiver—a 400-year-old French cultivar— and the old church apple, which is grown solely on Weston’s farm. You may want to take home a hard cider as a souvenir.

Head west on I-94, grab a beer in Madison, then drive on Highway 151 through surprisingly scenic western Wisconsin til you reach the Iowa border and Des Moines, Iowa’s handsome capital. Go a little farther south to the bucolic...

Bridges of Madison County, IA

Before the bridges of Madison County were the setting for a Clint Eastwood–directed film, they were the setting of a best-selling book. But before that they were . . . well, bridges—but awfully charming bridges that date back to 1870. Vivid autumn foliage makes the six remaining bridges an even better photo op, and spending a little time in this laid-back part of the country tends to lower one’s heart rate and stress levels.

Jump onto I-80, make a quick pit stop at the University of Iowa campus in Iowa City, and head towards the Mississippi River to drive down...

Great River Road, IL/MO

The Great River Road along the Mississippi River feels like one of the country’s most distinctly American roads, passing by numerous riverside overlooks, small downtowns, and even Mark Twain’s boyhood home (in Hannibal, MO). Many day-trippers converge on the route during the fall, enjoying colorful foliage on one side and the sight of the Mighty Mississippi on the other. On the way down, feel free to dart off the path to visit one of the many wineries scattered on both sides of the border.

Follow the Great River Road south as the Illinois-Iowa border becomes the Illinois-Missouri border. Before you come to St. Louis, you’ll take a...

Haunted Tour of Alton, IL

Cooler temperatures and rattling winds can give a town a spooky vibe, so there’s no better time to visit Alton, Illinois, and its famous haunted tours than the fall. Choose one of the town’s many guided tours and brace yourself during visits to limestone mansions, a haunted sanitarium, and a 180-year-old penitentiary that once housed Confederate POWs during the Civil War.

Take I-70 east through endlessly flat Illinois, spend a little time in Indianapolis, and then drive north on Highway 31 until you reach...

Rise n’ Roll, Middlebury, IN

The delectables of Rise n’ Roll Bakery, a small chain in the Indiana Amish Country, are so beloved that even Chicagoans are willing to make the two-hour drive for its pastries. The flavors of autumn are well-represented here—indulge in some cinnamon-caramel donuts and crunchy pecan pie, and then take home some apple butter, corn relish, and pecan pumpkin butter.

Head north on Highway 131, cross into Michigan, and follow the signs to Kalamazoo. There, you’ll toast your trip with a few drinks at... 

Bell’s Brewery, Kalamazoo, MI

Cheers to a wonderful trip at Bell’s Brewery, which MLive.com calls “the granddaddy of the Michigan brewery scene.” The brewery’s Eccentric Cafe always has 30–40 brews on tap, with many you likely won’t find in the stores. To complement a brisk autumn day, try the Rye Stout, the candy-apple-tinged Harvest Ale, or the chocolately Hell Hath No Fury Ale.

If you’re continuing your trip, merge onto I-94 along Lake Michigan and take it through Chicago. Consider stopping and taking advantage of the world-class attractions in the Windy City, but keep following I-94 into Wisconsin en route to New Berlin.

Photo: Beer 2 by Kate Borkowski under CC BY-ND 2.0