A Quick, Handy Guide to Chicago’s Best Fall Drives

Plus: three great destinations to make ‘em worth your weekend

By Moira Lawler

A Quick, Handy Guide to Chicago’s Best Fall Drives
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12 September 2017

Mourn summer’s end for too long and you’ll miss fall.

And no one serves up fall like the Midwest.

Best place to take it all in? From the road, of course.

So we mapped out three of the area’s most photogenic fall drives, along with where to stay and what to do once you get to your destination.

Before you start planning, you’ll wanna reference this map that tracking peak fall foliage around the country. Otherwise, get your road-trip playlists ready.

Michigan: Traverse City to Northport to Glen Arbor
Best time to go: End of September to early October

You’re committing to a long road trip, but if it’s glorious fall colors you’re after, there’s no better place in the Midwest (or in the country, really: USA Today readers named it the country’s best scenic autumn drive in 2015). Start in Traverse City and hop on M-22, which hugs the eastern edge of the Leelanau Peninsula. Head up to Northport and come down the highway along the Lake Michigan coast. Don’t miss the stretch between Big Glen and Little Glen Lakes: the fiery oranges and scarlets are why you came.

STAY: Call the Traverse City area your home base, specifically one of the two spacious homes that make up Lakemore Retreat. The houses share a hot tub and fire pit — the perfect finish to a crisp fall day.

EAT: As you head north on M-22, take a detour over to Tandem Ciders. Sample a few ciders at a picnic bench, and pick up a growler of their popular hard cider the Smackintosh for later. Once back in Traverse City, stop for dinner at the 26-seat The Cooks’ House. And save room for a slice at Grand Traverse Pie Company.

Wisconsin: Madison to Spring Green to Dodgeville
Best time to go: Early October

Head northwest out of Madison via US-12. When you pass through Sauk City, turn left onto WI-60, which follows the Wisconsin River into Spring Green. From there, you’ll want to make your way over to Highway 23. Pass over the river, and stop to check out Frank Lloyd Wright’s Taliesin home. Continue south to Dodgeville. You’ll drive through Wisconsin’s Driftless area, which means picturesque hills, ridges and valleys.

STAY: Peniel School #9, a 100-plus-year-old schoolhouse turned Airbnb you’ll want to move into. Or, if you’ve got a full car, opt for a larger house on a hill in nearby Blue Mounds.

EAT: Start the day with a cup of coffee from the much-hyped Bradbury’s Coffee in Madison. Later, hit up Bob’s Bitchin’ BBQ in Dodgeville for the best cheese curds around and, clearly, some bitchin’ barbecue.

Michigan: Indiana Dunes to New Buffalo to Tryon Farm
Best time to go: Mid-to-late October

This one here’s your closest option: you can get to the dunes in under an hour from the city. Stop at the 1933 World’s Fair Century of Progress Homes. Time it for October 14th, and you can tag along on one of the National Park Service’s tours. Afterward, head east on Highway 12 and follow The Dunes and Lake Driving Loop. But instead of turning around after the Beverly Shores neighborhood, head toward New Buffalo.

STAY: If you’re looking to make a weekend out of the drive, Tryon Farm is the place to do it. Peruse Airbnb for available rentals (for instance: 1, 2, 3), all of which offer modern, sustainable farmhouses tucked away in the woods.

EAT: For lunch, grab a piled-high Reuben from David’s Delicatessen in New Buffalo. While you’re up there, pick up some prepared foods and cheese from Whistle Stop Grocery to snack on at the house later. The next day, head back into Michigan for a cardamom-cinnamon-almond coffee cake from Harbert Swedish Bakery. There will be a line. Trust it will be worth it.

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