Photo: Train passing Hermann, Missouri

A train chugs past river bluffs outside Hermann, Missouri.

Photograph by Mary McClain, My Shot

Pop. 2,717
GPS: 38°42'N, 91°26'W

A Missouri-style nod to Europe's cycling-and-wine culture, Hermann has the country’s longest rails-to-trails track, a new bikable bridge, and the Tour of Hermann Bike Race—stoked by seven wineries nearby.

PLAY

First, get inspired: Hermann, MO Area Cycling keeps a blog with a roster of great routes in the area, varying in lengths between 20 miles (32 kilometers) and a whopping 103 miles (166 kilometers) (www.hermanncycling.blogspot.com). Next, rent some wheels at the Hermann Ride, Rest & Go Bicycle Shop, centrally located on Schiller Street ($15 a day; +1 573 486 9170). Now, pedal on and enjoy!

EAT

The historic Cottage Restaurant, set on 6 acres of walkable trails and stunning views of pastoral Hermann, is an experience in itself. With emphasis on all things local, the restaurant uses ingredients from Hermann’s farmer’s market and displays resident artists’ work in its dining room (www.goodfoodfineart.com).

SLEEP

The Captain Wohlt Inn, a stately 1886 home turned B&B, has cozy suites, fresh-made breakfasts served on the brick patio, and a convenient location in the historic district ($80, www.captainwohltinn.com).

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