Plan a Winery & Brewery Tour of Madison County, Iowa

Covered bridges and the John Wayne Birthplace might be what Madison County, Iowa, is known best for, but the hidden secret?! They have an abundance of great wineries & breweries to enjoy! After spending a weekend in their beautiful countryside recently, we can safely say that you and your special someone need to plan a winery & brewer tour of Madison County, Iowa.

*Special thanks to the Madison County Chamber of Commerce for arranging samples, food, and accommodations for our visit. All thoughts and opinions are 100% authentic and our own. For more details, please check out the Disclosure Tab.

Madison County, Iowa

Madison County is located in southwest Iowa, about 30 minutes from West Des Moines and offers beautiful rolling landscape. It is a booming community, but not overpopulated, so we’re sure you’ll enjoy the opportunity to slow down, relax, and enjoy your visit. Winterset is the county seat and the hub of all activities (and very centrally located), so it’s a great place to book a room and make it your home base for your trip.

Getting There

Madison County is easily accessible by both car and plane. Fly into the Des Moines International Airport, if needed, and rent a car to make the short drive!

If you’re traveling by car….

• Des Moines, Iowa – 40 minute drive time
• Minneapolis, Minnesota – 4 hours, 1 minute drive time
• Chicago, Illinois – 5 hours, 20 minute drive time
• Kansas City, Missouri – 2 hours, 38 minute drive time

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Easton ‘s Bistro

One of the most unique features of visiting Madison County & Winterset is partaking in a meal or two by private chef, Easton. We were treated to a private 4-course meal by Easton during our stay. We dined on delicious foods like blue cheese stuffed peaches, wrapped in prosciutto and baked. YUM! For our main course, Easton prepared Sous Vide Wagyu New York Strip, sautéed asparagus, and roasted baby red potatoes. All of it was amazing and it was evident that this is Easton’s passion!

Thankfully, Easton was able to accommodate my gluten allergy completely and without fuss. For dessert, he prepared us the most amazing dark chocolate crème Brule! Crème Brule is one of my favorite desserts and this version took it to a whole new level and was simply melt in your mouth perfection!

If a private dinner isn’t your speed, Easton cooks for the Bistro where he serves up lunch during the week days and breakfast on Saturdays!! Need a custom charcuterie board for snacking?! He can do that too! In fact, we quickly learned there isn’t much Easton can’t do.

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What to Visit – Covered Bridges

No trip to Madison County is complete without a tour of the covered bridges. 6 of the original bridges are still available to explore. Several of them were featured in the Hollywood hit, “Bridges of Madison County” with Clint Eastwood & Meryl Streep. My personal favorite were Cedar & Holliwell. Holliwell is actually the longest of the bridges, which spans 110ft over the Middle River. Most of the bridges are on several miles of gravel roads, so be prepared for that, but it’s definitely worth the drive to walk across the bridges, enjoy the views, and think about the history those bridges have seen!

Where to Visit – John Wayne Birthplace & Museum

The only thing more famous in Madison County than the covered bridges is John Wayne. Actor John Wayne, born Marion Morrison, was born in Winterset back in 1907 and even though he and his family moved away just a few short years later, his roots to Winterset have always been deep. Now, in the heart of downtown Winterset, you’ll find his birthplace and a museum dedicated to telling his story. Tour the exhibits, which feature authentic costumes, a car, wagon, and several movie set items plus a movie highlighting his acting career. Whether you’re a movie buff, love western movies, or just enjoy learning about American icons, you’ll enjoy a visit to the John Wayne Birthplace & Museum!

What to Visit – Wineries & Breweries

We know what you’re thinking….”my husband isn’t going to enjoy driving around looking at covered bridges”, but we do think they’ll enjoy trying out all the wineries & breweries in Madison County, which is a reason to plan your tour of Madison County today! Local wineries & breweries have been popping up all over Madison County for the last decade and that’s why it’s a great place to enjoy many of them!

1st Down Brewing

One of the newest breweries in Madison County is 1st Down Brewing Co. The owner took a leap of faith in the past year to open this brewery and we think he’s off to a great start! This is also the only brewery in downtown Winterset, which makes it walkable when staying at Winterset Wonderland! 😉 Not only is the building he’s chosen for his brewery is beautifully renovated to maintain the history, but the beer is cold and delicious! We highly recommend the Blind Side: Blackberry Wheat! We fell in love and are kicking ourselves that we didn’t bring any home to enjoy at a later date!

Covered Bridges Winery

Located north of Winterset on Highway 169, in a beautiful building with sweeping landscape, you’ll find Covered Bridges Winery. What started as a hobby over 10 years ago, has turned into a successful winery in the countryside of Iowa with several wines winning many awards over the years! Here, you can enjoy wine by the glass or flight of samples. They also offer a little bit of everything from a dry red to a sweet rose type wine. We recommend starting with a flight to decide what you like, but we also think you can’t go wrong with a glass (or bottle) of Holliwell Bridge! (And yes, we enjoyed this one so much we did bring a bottle home to enjoy later!)

The owners are not only dedicated to developing quality wine, but making your overall experience a memorable one. They offer meat & cheese boards, but also have a full set of events including wine & yoga and live music events.

Madison County Winery

Head East out of Winterset and travel across the rolling countryside to Madison County Winery. Tucked into the hillside is a quaint winery with a fun vibe. Outside they offer a large variety of seating including picnic tables, tables & chairs, fire pits, bags games, benches, and more. Inside you’ll find casual seating along with high top tables & chairs. Of course, pick a glass of wine (or a local brew if you aren’t a wine fan) or do a sample tray! Summer Blond & Pink were favorites of ours!

In additional to wine & beer, they participate lots of local events and offer live music and snacks! It’s a great spot to spend a couple of hours on a sunny afternoon!

More Options

Our weekend didn’t allow to visit all the brewery and winery options, but if you want to add on, you can also visit Big Rack Brew Haus and Winterset Cidery

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Where to Eat – Local Options

Don’t worry, on your winery & brewery tour of Madison County, you’ll have great options to soak up the alcohol. Winterset and Madison County definitely do not lack for local options for delicious meals!

Beans & Beignets

Earlham, is a town of about 1400 people located northwest of Winterset and downtown, you’ll find Beans & Beignets. Located in a beautiful historic building, this is a coffee shop, ice cream shop, and a spot for lunch or dinner. Several years ago, the community came together and decided to rehab this dilapidating building and find someone to move a business in and they did a great job with the finishes. They achieved maintaining the history of the building and new modern finishes too giving it a bright and comfortable feeling that is very warm and welcoming.

Now, owner Nina opened this local spot to cultivate relationships and community. The menu offers a great variety of items. For breakfast, pick from items like egg sandwich, French toast, and breakfast burrito. Lunch and dinner offers adult grilled cheese, salads, shareable plates, and more! Of course, beignets are also on the menu. Finally, it’s a great spot to grab a coffee, ice cream treat, or a sundae!

During our visit, I picked gluten-free toast (yes, YAY for gluten free options) and a fruit & yogurt parfait. The toast was great. I know that seems simple, but gluten-free bread is hard to find and maintain and they did a great job at it. The parfait was HUGE with vanilla yogurt and lots of fresh fruit with a sprinkling of granola. T opted for the breakfast burrito and it was stuffed to the brim with scrambled eggs, breakfast potatoes, cheese, and meat!

A great vibe, delicious food, and super friendly people make Beans & Beignets a “must stop” when visiting Madison County!

The Drift Taproom & Restaurant

Another great, conveniently located spot in Madison County is The Drift Taproom & Restaurant in downtown Winterset. Located across from the courthouse, The Drift is housed in yet another beautiful historic building. In fact, It’s so historic that its not allowed to have open flames so no grill or fryers allowed. But, that didn’t stop the owners from coming up with a delicious and creative menu.

I loved the renovations that had been done to the building where The Drift calls home. They did a great job of showing its history, but adding modern touches. The menu not only features flatbreads, salads, appetizers, and a variety of sandwiches, but they also boast over 20 Iowa beers on tap. They also offer an extensive cocktail menu including a Honey Old Fashioned and a Mulberry Mule.

During our visit, I was super excited to see that they not only offer a gluten-free flatbread crust, but also gluten-free bread for their paninis and sandwiches. T picked their Roast Beef Panini while I opted for one of my favorites, the Reuben. Of course, they take their Rueben to the next level with homemade 1000 Island dressing and fresh corned beef! T raved about his panini too saying that it had great flavor with bread that wasn’t too crunchy (a pet peeve of his). It was all well balanced and delicious. We both also picked side salads and they were generous sizes with lots of fresh veggies!

Whether you’re looking for lunch, dinner, Sunday brunch, or a spot to meet some friends for a drink, the Drift is a great pick!

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More Things to Do During Your Tour of Madison County

You might be exhausted, but there’s still so much more to do!

• Drive through Winterset City Park and check out Clark Tower with it’s amazing views!
• Make sure to walk the square in downtown Winterset and check out all the local shops & boutiques
• Enjoy murals and historic photos on the buildings in downtown Winterset
• Get ice cream from Frostee’s!
• Check out the Madison Freedom Rock near the John Wayne Birthplace & Museum.

Planning a tour of Madison County is a must. Men and women alike will enjoy all the local wineries & breweries. Visiting the historic covered bridges and more will make for a fun and relaxing weekend! Who’s ready to plan?!

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