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! 

Great Lakes
Great Lakes

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.

Great Lakes Relaxed
Great Lakes Relaxed

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

Intro to Road Touring - Wisconsin
Intro to Road Touring - Wisconsin

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 will be followed by a fun, four-day tour of the West Bend, WI area.

Katy Trail
Katy Trail

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.

Northern Tier
Northern Tier

Van Supported. The Northern Tier has been the location for great bike adventures for a quarter of a century, following a wonderfully diverse cross section of the North American continent. Between Bar Harbor, Maine, and Anacortes, Washington, lie places of extremes for you to discover.

Ohio to Erie Trail
Ohio to Erie Trail

Inn to Inn. Ride the Ohio to Erie Trail and connect the Ohio River on the Ohio/Kentucky border with Lake Erie to the north. This great 8-day tour will cover one of the longest continuous bike paths, also designated as Ohio Bike Route 1.

TransAm Express Westward
TransAm Express Westward

Van Supported. This take on a classic route should entice people who love riding trail systems. By riding the entirety of the C&O Canal Trail and Great Allegheny Passage in the east and Katy Trail in the Midwest before meeting up with the famed TransAm Trail in Colorado, this tour will have over 500 miles of bicycle paths and should be an experience of a lifetime for anyone looking for a transcontinental ride.

TransAm Westward
TransAm Westward

Self Contained. Thousands of cyclists have pedaled the 4,253-mile TransAmerica Trail and will tell you they captured a lifetime's worth of memories along their tour. For many traveling cyclists who haven't yet experienced the TransAm, it remains the holy grail of American bicycle tours.

Tour Team Top Picks

Florida Keys
Florida Keys

Van Supported. Get a second dose of summer with this Sunshine State ride. You can smile wide as you ride knowing you're enjoying 300 miles of sunny, warm weather!

Great Allegheny Passage
Great Allegheny Passage

Van Supported. Enjoy a long weekend of car-free riding on one of Pennsylvania’s most popular rail trails. Exchange the bustling urban center of Pittsburgh for the rolling highlands of Ohiopyle State Park and southern Pennsylvania’s vital river systems. Witness the history of the area’s once thriving coal industry, and the great push for conservation and preservation that has taken its place.

Hawaii 3 Island
Hawaii 3 Island

Inn to Inn. Maui, Molokai, and Lanai: three of Hawaii's most beautiful islands and the setting for an unrivaled bicycle travel adventure. This unique tour features a ferry and a small plane to bring together these three Hawaiian islands into a single bicycle tour.