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Road Trip Idea: Leaf Peeping and Breweries in the Midwest

BY: Editors | Sep 25, 2017

If you're itching for a great road trip idea, your first thoughts probably aren't of the Great Plains. But 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. So here's the plan: take off a week or two and follow this autumnal Midwest road trip to cross off all your seasonal activities at once.

Pro Tip: Since the route for this road trip idea 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.

Directions above are approximate. We recommend turning on the "avoid highways" feature for the most scenic route!

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.

Where to eat: Rosati's Pizza, which serves up classic Chicago-style pies
Where to stay: The Ridge Hotel in Lake Geneva

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 | Winterset, 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 is sure to lower one's heart rate and stress levels.

Where to eat: Rodell's Smokehouse, where you can fill up on barbecue
Where to stay: Des Moines Marriott Downtown in Des Moines

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 | Mississippi River, 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.

Where to eat: The Mark Twain Brewing Company for pub-friendly bites and a pint
Where to stay: Hannibal Inn in Hannibal, MO

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 | 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.

Where to eat: Pan D'Olive for a Mediterranean spin on hearty casual fare
Where to stay: Moonrise Hotel in St. Louis, MO

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.

Where to eat: Amish Acres, which lets you dine on a real Amish farm
Where to stay: Waterford Estates Lodge in South Bend, IN

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 classic Midwest 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.

Where to eat: Kalamazoo Pizza Company, which fans call a "hidden treasure"
Where to stay: Four Points by Sheraton in Kalamazoo

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.