Tours in the Midwest

If you think the entire Midwest is pancake-flat, you’ve got another thing coming. The middle of America is a prime cycling destination with hundreds of miles of rail trails, paved cycling paths, and empty country roads — not to mention some incredibly vibrant communities large and small. A tour in the Midwest can take you through rolling farm country, along meandering rivers, and next to pristine lakes (including a few particularly “Great” ones), and — yes — up and down more hills than you might expect! 

2020 Great Lakes - Inn to Inn
2020 Great Lakes
Jun 06, 2020 - Jun 16, 2020

Inn to Inn. Enjoy incredible scenery and some of the best riding you can imagine on this inn-to-inn adventure. You’ll enjoy great riding with minimal gear and the added luxury of a roof over your head and a warm bed each night. Coupled with the route’s moderate terrain and manageable daily distances, this trip makes an excellent choice for beginners or for those wishing to enjoy more time out of the saddle during their vacation.

2020 Intro to Road Touring - Wisconsin
2020 Intro to Road Touring - Wisconsin
Jun 14, 2020 - Jun 19, 2020

Self Contained. As the experts on self-contained bicycle travel, we’d like to share our knowledge by offering our Introduction to Road Touring (IRT) course. Two days of open-air, informal campground discussions — including the classic panniers vs. trailer debate — will be followed by a fun, four-day tour in and around West Bend, Wisconsin.

2020 Lake Superior South Shore
2020 Lake Superior South Shore
Aug 16, 2020 - Aug 27, 2020

Self Contained. Join us on a tour of the Keweenaw Peninsula, the northwestern-most part of Michigan’s Upper Peninsula. The Keweenaw Peninsula is on Lake Superior, one of the largest freshwater lakes in the world, making it a place of rugged beauty and breathtaking vistas.

2020 Route 66: Chicago to St. Louis - Van
2020 Route 66: Chicago to St. Louis
Aug 29, 2020 - Sep 05, 2020

Van Supported. The phrase “Route 66” evokes visions of the Great American Road Trip. Today the bicycle is the vehicle of choice for many looking to get their kicks on the Mother Road across the Prairie State.

2020 Katy Trail - Inn to Inn
2020 Katy Trail
Sep 12, 2020 - Sep 19, 2020

Inn to Inn. There might not be a trail in the U.S. better suited for a relaxed ride than Missouri’s popular Katy Trail. Car-free, virtually flat, and featuring a crushed-limestone surface, the trail dishes up plenty of towns and attractions (and ice cream stands) along the way to keep things interesting. This tour is perfect for any wanderer who enjoys meandering through small towns and stopping to smell the roses.

2020 Great Lakes Relaxed
2020 Great Lakes Relaxed
Sep 19, 2020 - Sep 26, 2020

Fully Supported. We’ve incorporated the quiet roads and pleasurable riding of Michigan’s Upper Peninsula into our popular relaxed tour format.

Tour Team Top Picks

2020 Great Divide Canada I
2020 Great Divide Canada I

Self Contained. Ride the Great Divide’s spectacular Canadian section and see why Outside magazine called it one of “The Best Backcountry Adventure Trips in America.”

2020 C&O Canal/GAP - Spring
2020 C&O Canal/GAP - Spring

Self Contained. This spring, you won’t need to worry about traffic as you ride your hybrid or mountain bike some 330 miles on hard-packed, gently graded gravel and dirt trails from the heart of the nation’s capital north to Pittsburgh, Pennsylvania.

Ragin' Cajun Country
Ragin' Cajun Country

Fully Supported. Bicycle through the heart of Cajun Country and partake of all the food, music, and culture that Acadiana has to offer. On this relaxed tour you can enjoy jambalaya, crawfish pie, and gumbo, and you’ll find that the spicy cuisine of southern Louisiana is complemented by its mellow terrain.