Mid West Motorcycle Tour

Self-Drive Tour 8 Days / 7 Nights
Tour Map
  • 1050.0 mi = 1680.0 km
  • Summer, Spring, Fall
  • 30.0 - 90.0°F = -1.1 - 32.2°C

For 8 days, EagleRider’s Mid West Motorcycle Tour will guide you on an unforgettable journey around Illinois, Missouri, and Wisconsin. Be prepared for a great ride as you tour Route 66 on your Harley from Chicago to Springfield and into St. Louis. You will cross the Mississippi River and head towards Milwaukee to visit the birth place of Harley-Davidson! Be sure to take a tour of the Harley-Davidson’s Capitol Drive power train operations while you are there. Your self-drive tour will end as you take a scenic cruise along the shores of Lake Michigan back into Chicago. EagleRider’s Mid West Motorcycle Tour is the perfect adventure for every motorcycle enthusiast!

Tour Itinerary

Arrive at Chicago International airport and transfer to your hotel. Overnight.
This morning you will pick up your motorcycle and your ultimate American roadtrip can begin. Parallel to I-55, the legendary Route 66 began its run here, cutting through the state before running all the way to the Pacific Coast – you will get a glimpse of it, as some old-time diners and other Americana still stand. Stop for some great pictures at the Gemini Giant in Wilmington, the Polka Dot Diner in Braidwood, the Old Log Cabin in Pontiac and visit some great old gas stations en route to Springfield, the Illinois state capital. Here, Abraham Lincoln honed his legal and political skills. Overnight.
Around Springfield you can discover some of America’s most significant historic sites: Lincoln Home National Historic Site, New Salem Historic Village and the Dana-Thomas House by Frank Lloyd Wright. Continue south and ride along Route 66. You might want to stop at Cahokia Mounds, the site of the largest prehistoric Indian civilization north of Mexico. The nearest town to the Cahokia Mounds is Collinsville, a pleasant little place that’s famous for its 170-foot-high world’s largest catsup bottle! You cross into Missouri and ride over to the old Chain of Rocks Bridge – it’s the world’s largest pedestrian and biking bridge. Head to St. Louis, where you overnight.
Today’s trip will take you north of St. Louis, for a stop in Hannibal, Missouri, boyhood town of author Mark Twain. Then it’s back across the Mississippi River to Illinois. You head to Galesburg, home to America’s poet Carl Sandburg, who immortalized Chicago as “the city of big shoulders”. Visit Seminary Street Historic District, which is one of the Midwest’s success stories in downtown restoration and revitalization. Overnight.
From Galesburg take Hwy 74 up to Moline, a quaint little town. Here, you cross the Mississippi River and continue your ride up north on Hwy 67, along the Mississippi, all the way up to the neat little town of Galena, just a few miles short of both Iowa and Wisconsin in the far northwest corner of Illinois. This place has changed little since its 19th century heyday. Thanks to its sheltered location, only a few miles up the Galina River, it was a major port of call for Mississippi River steamboats. You head to Madison, Wisconsin, where you overnight.
History books record that Madison was little more than a wooded, mosquito infested swamp when it was selected to the political nucleus of the Wisconsin Territory in 1836. Today this stimulating, youthful metropolis is one of the most beautifully set cities in the US. You ride just over an hour west on Hwy 94, towards Milwaukee – a must for every Harley rider, since this is where Harley Davidson was born and reborn! You should begin in the suburb of Wauwatosa with a free tour of Harley Davidson’s Capitol Drive powertrain operations. See displays of flatheads, panheads, knuckleheads and shovelheads, as well as H-D photos and memorabilia solicited for the archives. Wrap up the day the way locals do: digging into a bratwurst, sitting in the stands at a game, hanging out in the historic Third Ward or on Water Street. You overnight in Milwaukee.
This morning you might want to check out Milwaukee's other institution – Solly’s Coffee Shop. Since 1936, locals and savvy travelers have been settling in at Solly's '’ horseshoe counters, where Milwaukee waitresses serve up hearty breakfasts, buttery sirloin burgers, and hand-scooped malts served in a steel can. Enjoy a scenic ride along the shores of Lake Michigan back to Chicago, the largest and most exciting of the Great Lake cities. Chicago has a skyline to rival any city’s, a gamut of top-rated museums, restaurants, cafes, and innumerable bars and nightclubs that pay homage to the city’s strong jazz and blues heritage. Upon arrival in Chicago it will be time to return your motorcycle and transfer to your hotel. Overnight.
Today your exciting trip will end with your departure flight back home.
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