Visit This Cute Iowa Town for Idyllic Photo-Ops, Alpaca Hikes and Hollywood Stardust

In the classic 1995 film The Bridges of Madison County, based on the novel by Robert James Waller, Clint Eastwood plays a photographer who treks to Iowa to shoot historic covered bridges—and instead finds Meryl Streep. (If only we were all so lucky.) The movie sparked global interest in Winterset, a sweet town with a well-preserved town square that’s a great day trip from Des Moines or weekend getaway from the Kansas City metro. The Madison County Covered Bridge Festival in October is a popular time to visit, but here’s how we’d spend a day in Winterset, any time of year.

9 a.m. Start with Carbs

An intoxicatingly sweet aroma and a sign in the front window advertising apple fritters—two solid reasons to start your day at The Bakery Unlimited. It’s the kind of place where you might overhear locals trading town gossip while you peruse the donut case. They sell all the classics, plus novelties like a maple donut with a full strip of bacon on top. Another great morning option is Petite Cafe, a tiny slip of a bakery serving pastries such as ham and cheese croissants and berry danish, as well as breakfast burritos and grab-and-go lunches. (Don't miss their iced honeysuckle latte.)

9:30 a.m. Walk in the Park

You can't go to Winterset without seeing at least one of Madison County’s iconic covered bridges. Perhaps the most convenient is the Cutler-Donahoe Bridge in City Park.  After snapping a photo of the picturesque span, walk along the trail to see Clark Tower. Dedicated to pioneer settlers of Madison County, the limestone, castle-like tower has a winding staircase you can climb. (Want to see all the bridges? The welcome center offers a handy map.)

11 a.m. Pick a Museum

Winterset was sprinkled with stardust (or perhaps with True Grit?) long before Clint and Meryl waltzed into the town’s lore: John Wayne, aka The Duke, was born here. At the John Wayne Birthplace & Museum, learn about the actor’s humble roots and cultural impact on a tour of the one-bedroom house his parents rented, about a block from the center of town. The museum is packed with an extensive collection of artifacts, including costumes, set props and fan mail. Alternatively, visit the Iowa Quilt Museum, where rotating exhibits—four each year—highlight the art and craft of quilting.

1 p.m. Stop for Lunch

Run by a husband-wife team and open for lunch only (and breakfast on weekends), casual Easton's Bistro sits just a block off the square. Peek into the open kitchen, chat with other diners at the communal seating—and don’t skip out on the pillowy and locally legendary cheesecake. Another lunch option (but you have to go early, as they close at 1 p.m.) are the grab-and-go items at Petite Cafe.

2 p.m. Stroll the Square

Be sure to stop and admire the historic Madison County Courthouse, capped by a striking dome (pictured above). It was built in the 1870s at the exact geographic center of the county, and like several of the town's buildings, it's listed on the National Register of Historic Places. Nearby, browse antiques (and also flavored coffee and crystals) at Harvest Creek. Brick Road Books is a new addition to the square; get lost in their collection of historical fiction, biographies, fantasy and cookbooks. If you’ve visited the Iowa Quilt Museum and your fingers are itchy to stitch, pop into Piece Works Quilt Shop for your next project’s supplies. 

4 p.m. Sip Local Wine

For happy hour, head to the tasting room at Covered Bridges Winery, one of eight stops on the Heart of Iowa Wine Trail. Their wines are made with Iowa-grown, French-American hybrid grapes and span the sweet white Edelweiss, punchy Francesca’s Folly rosé, or State Fair gold-winning Rattlesnake Red. On Saturday evenings in the summer, come out for Music at the Winery, featuring up-and-coming Iowa artists.

6 p.m. Stay for Dinner

At The Drift on the town square, string lights hang over a patio nestled between two brick buildings. Sip on a craft cocktail inspired by the town, and dig into dishes like popular mushroom and goat cheese flatbread or flaky white-wine chicken pot pie. 

8 p.m. Save Room for Ice Cream

Stroll around the square and order a (family-friendly) nightcap from Frostee's, a quintessential ice cream stand just a block away from the courthouse. Choose among cones, sundaes or Cyclones, and don’t be surprised if there’s a line—while Frostee’s serves up frozen treats, it’s one of the hottest places in town. 

Explore More

Winterset has two standout farms that aren’t open daily—but are absolutely worth visiting or even planning a trip around. The first is Rusty Stars Alpacas, where on Saturdays, visitors can hang out with the herd or even get matched with a hand-picked alpaca (think of it like a personality test) for a country hike. The second is Pepperharrow, a cut-flower farm that hosts periodic U-pick events, lavender field dinners and workshops; if you sign up for an event, check out their bespoke farm shop, selling lavender soaps, tea, candles and more.

If you’d like to take a hike in the area, visit Pammel State Park, where woodlands converge with the rural landscape along a limestone ridge.

Spend the Night

For a memorable stay in the area, check out the Covered Bridge House, a serene farmhouse just a short drive outside of town. It was constructed by the Eli Cox family, who actually built many of the area’s bridges, so it’s the perfect full-circle place to stay after exploring the area.