This is a suggested self-guided tour for seeing highlights of Madison County in a half day with your own transportation.

The times are approximate, based on your own pace and interests.


  • 9:00 am – Start the day at Madison County Chamber of Commerce’s Welcome Center, located at 73 Jefferson Street in Winterset’s town square, to pick up a free map of the locations of the six covered bridges in the county, as well as their other attractions. The Welcome Center is also where you’ll find public restrooms, souvenirs and locally-made products, including bottles of wine from all three of Madison County’s wineries. If you skipped breakfast, be sure to pick up an apple fritter from The Bakery Unlimited (119 John Wayne Drive) before you head out. See more restaurant options here.
  • 9:30 am – Arrive at City Park in Winterset (enter at the corner of 9th Street and South Street). Walk across the Cutler-Donahoe Covered Bridge, stroll through the English Hedge Maze (and see if you can find the hidden sundial), then hike or drive the two miles roundtrip to Clark Tower (one of Madison County’s best photo ops).
  • 10:00 am – Visit Holliwell Covered Bridge, featured in the movie The Bridges of Madison County. Be sure to walk down to the edge of Middle River for a great view!
  • 10:30 am – Visit the Roseman Covered Bridge (where Robert first sought directions from Francesca in the movie, and where Francesca requested her ashes be scattered), and stop in the gift shop (open in May through the summer, Fridays-Mondays, 11 am to 6 pm).
  • 11:00 am – Explore Winterset’s fantastic shops along its historic town square, especially local favorites Pine Creek Ltd, Madison County Mercantile, Angel Wings & CT. Don’t miss 1st Avenue Collective where you can shop for handcrafted items in the county’s old jailhouse! See more great shopping destinations here.
  • 12:00 pm – Enjoy a true Midwest lunch at the Northside Café (61 E. Jefferson Street), such as a huge Pork Tenderloin or the Hot Beef Sandwich, or choose one of their specialty salads if you prefer lighter fare. If you still have room for dessert, be sure to order their blueberry crisp or a slice of homemade pie. See more restaurant options here.
  • 1:00 pm – Tour the only museum in the world dedicated to Hollywood legend John Wayne. The John Wayne Birthplace & Museum (205 S. John Wayne Drive) honors Winterset’s own in grand style.  Be sure to pose with the full-size John Wayne bronze statue out front.
  • 2:00 pm – Depart Winterset, stopping on your way out of town to pick up a refreshing soft-serve cone or Cyclone at Frostee’s (101 E. Green Street).


*Based on the results of a community-wide tourism survey conducted in May 2016 by the Madison County Chamber of Commerce.