Think the Midwest is all cornfields and flat highways? Think again. From remote gravel adventures to lakeside loops and wine-country rail-trails, this region is a two-wheeled playground hiding in plain sight. Whether you're chasing solitude or small-town charm, here are five unforgettable bike trips in the Midwest, including one unscripted ride that throws out the itinerary and lets instinct lead the way.

‍

‍

1. The Driftless (Wisconsin)

Carved by glaciers that never came, the Driftless Region delivers steep climbs, winding descents, and wide-open views that feel like a secret worth keeping. Lost Travel’s Lil’ Drifty ride takes full advantage of the terrain—mixing gravel backroads, remote campsites, riverside trails, and the kind of unexpected detours that become stories you tell for years. It’s part bikepacking trip, part social experiment, and fully off-script.

‍

2. Katy Trail State Park (Missouri)

Stretching 240 miles across the state, this rail-trail is ideal for long-haul cyclists looking for mellow grades, river scenery, and wine stops. Riders pass through a mix of farmland, forests, and charming towns with plenty of campgrounds and B&Bs along the way. It’s a perfect blend of comfort and countryside.

‍

3. Cuyahoga Valley Towpath Trail (Ohio)

Running through a national park, this 87-mile trail is a favorite for weekenders. The smooth path parallels the old Ohio & Erie Canal, with options for detours to waterfalls, scenic overlooks, and local cafes. Ride in spring for wildflowers or autumn for peak foliage.

‍

4. Paul Bunyan State Trail (Minnesota)

The Midwest’s longest continuously paved trail cuts through northwoods, lake country, and resort towns. Stop in Bemidji for a lakeside lunch, or camp along the shorelines. Ideal for a relaxed summer adventure or colorful fall getaway.

‍

5. M-22 Scenic Ride (Michigan)

Wind along the Lake Michigan shoreline on this iconic 116-mile loop. Dunes, lighthouses, and hidden beaches line the road, along with small towns and local food stops. It's a cyclist’s dream if you love open roads and waterfront views.

The Midwest might not brag about its beauty but maybe that’s what makes riding here feel so raw and real. These five routes offer more than just scenery. They give you freedom, connection, and a few surprises along the way. Ready to ride off-script? Start with Lil' Drifty. You bring the bike. We’ll bring the adventure.

‍