The Small City In Iowa With World-Famous Covered Bridges And A Passion For Cute Small Businesses

Travelers, you might not realize that Iowa is an underrated gem with much to offer. The Hawkeye State is home to one of the best destinations for wine lovers in the Midwest and one of the most unique roadside stops in America. Iowa is also full of quaint towns, such as Winterset in Madison County. Located less than an hour drive from Des Moines, Iowa's capital, Winterset has a population of less than 6,000 people. Despite being a small city, Winterset has gained widespread fame for its picturesque and historic covered bridges. Madison County has six covered bridges and five can be found in Winterset.

However, the town also has a number of charming small businesses and eateries to enjoy. This includes Montross Pharmacy, a nostalgic spot with a gift shop, soda fountain, and lunch counter. There's also Petite Cafe. The adorable white brick building is the place to go for java and pastries. For unique finds, shop at White Cottage Market or Harvest Creek. Are you a DIY enthusiast? Check out Piece Works Quilt Shop. At The Drift, you can dine on flatbreads, sandwiches, wraps, and salads, while sipping on specialty libations.

Nevertheless, Winterset's crown jewels are its covered bridges. They were the subject of the movie "The Bridges of Madison County." In 1995, Clint Eastwood directed and starred in the film alongside Meryl Streep. It was an adaptation of Robert James Waller's book by the same title, which was published in 1992. Notably, Oprah Winfrey loved the novel so much she featured Winterset's Cedar Bridge on "The Oprah Winfrey Show" in 1993. Needless to say, they are a must-see during your time in Winterset.

Winterset's landmark structures date back to the 1800s and are spread throughout the town. The bridges include the Cedar, the Cutler-Donahoe, located at Winterset City Park, the Hogback, Holliwell, and Roseman Covered Bridge (pictured). In fact, the last two can be seen in the movie. That said, if you want to visit these landmarks, Viator features a personal guided tour of the covered bridges of Madison County. All but the Cedar are included in this two-hour, all-ages activity, which is provided by the Madison County Chamber of Commerce in Winterset. Its building on E Jefferson Street is the starting and ending point of the excursion. Likewise, per the Viator listing, a personal vehicle is needed. During the tour, attendees will gain historical insight of the covered bridges, snap photos, and more.

This activity has a 4.5-out-of-5 rating, with several reviewers saying that the experience is worthwhile because of the insight shared by local guides. The personal guided tour of the covered bridges of Madison County is offered daily with various departure times. As this is an outdoor activity, consider booking in spring or early fall when Winterset has its mildest temperatures.

Winterset hosts the Madison County Covered Bridge Festival in October, which should be added to the list of the best celebrations held during the fall in Iowa. If you're looking for more attractions in Winterset, the John Wayne Birthplace Museum and the Iowa Quilt Museum should be added to your itinerary. If you need a place to stay, the Cobblestone Inn & Suites is ranked as the best hotel in town on Tripadvisor. Note that the closest major airport to Winterset is Des Moines International Airport.