One of the Best Day Trips from DSM. And It's Only 40 Minutes Away

Have you been to Winterset lately? Honestly, I can't think of a better day trip this close to DSM. And yes, I'll tell you where to eat. Here's a great one-day itinerary.

Greetings! I’ve found that my articles on nearby travel destinations are some of the most read and shared posts I write. Here’s another!

I’ll also tell you about a great thing to do on August 10. Plus, tell me where you’d like me to go next—what Iowa (or Iowa-adjacent) spot would you like me to report on for my next travel story?

But first, here’s Winterset. Really, stay with me—it’s a lot better than when I (and maybe you) went last, and well worth a visit!

More Than Bridges, Believe Me

I’m not sure exactly how long it’s been since my last visit to Winterset—maybe 12 years?—but it wasn’t a great trip. The town square felt in flux, like it could tip in either direction, and the restaurant I’d made the drive to visit was not worth writing about. At one point, I talked to the proprietor, who crabbed about how bad business was and then asked me if I wanted to be an investor in the place. Go figure. The place has long closed, btw.

These days, Winterset is a very happy place, complete with the kind of vibrant small town square you hope to find, but rarely do. Throw in the lovely parks and countryside, and I cannot think of a better day trip that’s this close to Des Moines. Bookmark my little guide for a joyful trip as summer comes to a close and as road-trip-perfect autumn days loom on the horizon.

Here’s an itinerary for a one-day visit:

10 a.m.: A Morning Hike (Complete with a Covered Bridge)

Winterset's 76-acre City Park rivals any park in Des Moines for its offerings. Where else will you find a covered bridge, a hedge maze, vintage stone shelters, bocce courts, a skate park, a 2.3-mile loop hike to a stone tower, and more? All photos by me unless otherwise specified.

Head to City Park. Conveniently, one of Winterset’ famed covered bridges was moved to this expansive 76-acre park in 1970. That means you don’t have to travel gravel roads to get to one (of course, some folks will think part of the charm of visiting covered bridges is traveling gravel roads to get to them). Poke through and around this bucolic park, which includes the circa-1870 Cutler-Donahoe covered bridge, gracious limestone picnic shelters, a hedge maze, bocce courts, and a skate park. If you wish, hike a 2.3-mile loop hike to Clark Tower, a limestone tower built in 1926. It offers views of the Middle River Valley. You can also drive to the tower.

A 2.3-mile loop hike takes you to this stone tower. You can also drive. Photo attribution.

👉 Alternate: If you want to be more away from it all—and visit a bridge that’s actually in the country—go to the nearby Pammel State Park. I visited the Nature Lodge there for a meeting, but didn’t have time to explore the park itself. Here’s an overview, with a downloadable map that includes hiking trails. The historic Roseman Covered Bridge (prominently featured in the film The Bridges of Madison County) is approximately 6 miles (a 14 minute drive) from this park.

Lunch: Pack a Picnic or Dine at Urban on the Square

Salmon BLT, chicken club. I appreciate alternatives to the usual fries, including garlic green beans and sweet potato fries. At Urban on the Square.

I can rarely resist a picnic, especially in a vintage stone shelter, like those in City Park. But I certainly dined well at Urban on the Square. It’s owned by Dave and Jean Thompson, who also own Urban Grill in Urbandale and other well-known spots in the metro area. We had handsomely presented, well-prepared salmon BLT and chicken club sandwiches.

👉 Tip: Urban on the Square is not open in the evening; when asked about this, a manager mentioned they were having a hard time finding enough staff to keep the standards high. They may well open evenings in the near future, but plan on daytime dining for now.

Afternoon: Museums + Shopping on the Square

Note that the museums are open seven days a week, except some holidays; however, many shops are closed on Sundays, and a handful have limited hours (such as Thursdays through Saturdays).

The county courthouse is the jewel in the crown of the town square; the Iowa Quilt Museum is housed in a former J.C. Penney store.

• The John Wayne Birthplace & Museum. Tour the modest four-room home where John Wayne was born and visit the museum, with memorabilia from movie posters, to set pieces, costumes, and props. A movie theater shows a John Wayne documentary.

• The Iowa Quilt Museum: Housed in a former J.C. Penney building, this museum honors the art of the American quilt through rotating exhibits of historic and contemporary quilts.

Historic buildings on the Winterset square; many have fascinating historical markers outlining the history and former occupants of each building. It's like an outdoor museum of 20th century small-town life!

• Shopping on the Winterset Town Square: Not only are most of the late 19th/early 20th century buildings in great shape, many are filled with eclectic shops that are well worth poking into. A few examples: Harvest Creek (candles, books, crystals, antiques, gifts, etc.), Quest Haven Books and Comics (which also includes games and a super soda bar), Spoons Full of Sugar Boutique (clothing, jewelry, salvage furniture), and custom jeweler b. shannon designs.

The Iowa Theater in Winterset shows first-run movies and, on Thursdays, Hollywood classics. The interior view was taken from the balcony during an Iowa Writers' Collaborative event.

Reasons to Stay Longer … or Even Spend the Night

It might seem silly to spend the night in a town that’s only 40 minutes away, but there are a few reasons to linger here. If you’re the camping type, both City Park and Pammel State Park offer campgrounds. Because we were in town for an Iowa Writers’ Collaborative retreat and function, we stayed at the modern and cheerful Cobblestone Inn and Suites just outside of town.

Why stick around? The beautifully restored Iowa Theater is also a small-town jewel. They screen first-run movies on weekends and Hollywood classics on Thursday nights. I watched the documentary Storm Lake, a special screening held for members of the Iowa Writers Collaborative and their guests.

There’s real pleasure in sitting in this vintage, narrow, high-walled theater, with its velvet curtain glowing under soft light, hearing the buzz of everyone catching up before the show. There’s also something moving about watching a film the way your grandparents’ generation did. And honestly, I think movies hit differently in a place like this; the experience feels more intimate and more communal. I loved it!

If you want to catch a quick dinner beforehand, check out The Drift, also on the square. While I wouldn’t call this a destination restaurant, the welcome was warm, and the flatbreads and impressive selection of beers on tap hit the spot.

If it’s still summer, head to Frostee’s, just off the square (near the Iowa Theater) for some ice cream at this cute and quintessential small-town ice cream shop.

Where Should I Go Next?

Help me decide my next destination. Which area/town/city would you like to know more about. Note—don’t vote for something that’s your favorite spot already; rather, vote for something you’re curious about!

Also, feel free to offer other suggestions in the comments section!

By the way, you can find all previous travel stories right here. These include trips to K.C., Omaha, Keosauqua, Kansas City, Dubuque/Upper Mississippi, Iowa City, Itasca State Park (MN), Door County (WI), Minnesota’s North Shore, plus road-trip-worthy restaurants in Mason City, Fertile, and Cedar Rapids.

That’s a lot of really useful information, with no hype: I’m totally candid at every turn. To remain free from conflict of interests, I never take freebies! If you’d like to help support my work, please consider a paid subscription.

I’ve Got Your August 10th Afternoon/Evening Planned for You

Wolf Wolf Green = two guitars and a ukulele playing acoustic rock and blues. Catch us at the Iowa Distilling Company in Cumming, this Sunday, from 3 to 5 p.m.

The Iowa Distilling Company in Cumming is a nice spot to pop in for a late-Sunday- afternoon libation—especially this Sunday, when our trio Wolf Wolf Green will be playing. Dave Wolf (aka my husband, Mr. Sportcoat) and I, along with Mark Green, play acoustic rock and blues, including covers, originals, and B-side favorites you’ve forgotten but love to be reminded of. Come on out for a drink or two.

When: August 10, 3 to 5 p.m.
Where: Iowa Distilling Company, 4349 Cumming Ave.
What: Music. Cocktails and a limited selection of beer + Music
Cost: No cover!

P.S.: This handsome barroom does not serve food; however, you can bring in your own if you’d like. Cheese, nuts, crackers, charcuterie, Casey’s pizza—whatever. If you, like me, need to eat when you drink, they don’t mind a bit!

While you’re in the area, after the place closes down at 5 p.m., why not swing on by The Ciderhouse Restaurant at Wilson’s Orchard, a stone’s throw away, and enjoy a pizza on their patio? Here’s the review I wrote a couple weeks ago.

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