Start from 20 curated places around Winterset, IA, then choose the recommendations that fit your guests.
Restaurants & cafés
Montross Pharmacy
The county's oldest family-owned eatery, an old-fashioned soda fountain with swivel stools right on the courthouse square. Order a hand-dipped chocolate shake with the house-made cola; it doubles as a working pharmacy and gift shop.
Mi Pueblito Mexican Restaurant
A family-run Mexican spot in a historic two-storefront building on the square, with fresh chips and salsa and enormous portions. Ranked among the town's top restaurants, it is a share-an-entree kind of place.
Trails & outdoors
Winterset City Park
A wooded city park with trails, the Cutler-Donahoe covered bridge, Clark Tower, a hedge maze, and limestone bluffs, all walkable from downtown. A great low-effort alternative to the rural bridge loop.
Clark Tower Loop
An easy loop through the city park to the limestone Clark Tower, passing the covered bridge and the hedge maze along the way. The trail shares the park road with cars and has no sidewalk, so stay alert.
Things to do
Covered Bridges Scenic Byway
A self-guided driving loop linking all six historic covered bridges through Madison County's rolling farmland. Pick up the free map at the welcome center and plan a few hours; some bridges end on gravel, so skip it after heavy rain.
Madison County Historical Complex
A multi-building living-history complex on the edge of town, anchored by a limestone mansion and including a depot, schoolhouse, church, and a barn of antique farm machinery. The Victorian-furnished mansion is the crown jewel.
Landmarks & sights
John Wayne Birthplace & Museum
The restored four-room house where the actor was born, paired with a sizable museum of film memorabilia, costumes, scripts, and his last custom car. The house tour next door is the highlight; admission covers both.
Roseman Bridge
The most famous of the county's six covered bridges, a lattice-truss span that featured heavily in The Bridges of Madison County. Visitors still tuck handwritten notes into the interior beams, a tradition from the film.