If “go big or go home” is your battle cry, immediately add the Katy, the longest developed rail trail in the country at 240 miles, to your bucket list. A good portion of the Show-Me State stretch, which practically spans the width of the 24th member of the U.S., follows in the footsteps of Lewis & Clark’s 1800s expedition as it winds along the mighty Missouri from Machens to Boonville before shooting south and ending near the shores of another of Missouri’s best water features, Lake of the Ozarks. Some geography—grassy fields, wooded groves, tall limestone cliffs, undeveloped riverbanks—would sill be familiar to the explorers. Stone tunnels and historic bridges aren’t the only reminders of the K-T’s past life in locomotion (the Missouri-Kansas-Texas Railroad, which was nicknamed K-T, or Katy). Restored depots, crossing signals, and other equipment remnants, and even the occasional passenger car pop up here and there.
When the clock strikes wine o’clock, be sure to be near Augusta or Hermann, a hamlet steeped in German-American heritage that can be reached using a three-mile connector bike path, as they make up a bulk of the developing Midwestern wine country. If you prefer antiques to vintages, drop by Rocheport.