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Known locally as “Devil’s Boot Cave,” this natural overhang carved in sandstone resembles the shape of a boot and stretches roughly 25 feet deep and wide, near Marthasville. Once used as a pioneer shelter and noted by local schools for nature trips, the site offers a little geological curiosity beside the trail—a hands-on reminder of Missouri’s limestone landscape and early frontier life. Great for a quick stop and photo op!

The Medford Trailhead for the Rock Island Trail offers ample parking, drinking water, and toilets. This is the best place to fill your water bottles for many miles, not matter which direction you're headed.

Big Creek is a picturesque stream that crosses the Rock Island Trail under a well built foot bridge. The shaded bench invites you to rest and enjoy the sound of running water and wind through the trees.

On the practical side, the Rocheport Trailhead for the Katy trail provides an excellent access point. There is plenty of parking, benches, and restrooms. There is a restaurant right next to the trailhead as well.

Rocheport is know to be a peaceful escape with its scenic Katy Trail, charming bed and breakfasts, award-winning winery, and quaint shops. Founded in 1825, the town retains its small-town charm, inviting visitors to explore its hills and bluffs, enjoy local dining, and discover artisan galleries. With a variety of activities and events, Rocheport provides a perfect spot for a weekend getaway or day trip, where you can stroll through town, taste local wines, and immerse yourself in the beauty and history.

take the time to stop and enjoy the view while crossing the bridge

One of 3 major highway bridges over the Missouri between Weldon and St Charles, MO. The KATY trail through here is as smooth as concrete and the scenery is beautiful!