#RAGBRAI · Family Adventures · Museums and History · South Central Iowa

Scouting RAGBRAI-2019: Winterset’s History of Good Times is RAGBRAI-Ready

Party like it’s 1899, Winterset! I think the youngsters on the far right would fit in with RAGBRAI just fine.

Winterset, IA: Madison County

Our first visit to this area was a fun one back in 2016. We had two hours to kill and we made it happen by packing in a lot of their beautiful City Park. You can click here to see what that was all about and then imagine all the great thing you can do in a full day, night, and morning. That’s our specialty when we scout towns on the RAGBRAI route and Overnight #3 gave us the uniqueness we were craving!

We had the pleasure of being hosted by some amazing folks, here in Winterset. Some of the meals and accommodations were complimentary.  The views expressed are always of our own. Let’s Gallivant this town!


Look out for the Pammel Park Road turn and shortly thereafter you’ll find the break you’re looking for.


I know some of you want to stop even more now!

The ride goes by many gravel roads and if there is going to be just one you take, you may want to give the path to Pammel Park Coffee Company as you get into Winterset. Not only is the coffee here roasted, brewed, and cared for by one of the state’s experts, it’s all done with a family business feel. Riders love rural Iowa, farms, and supporting locals. You can experience all of that with every slurp of their delicious brew. They take time to educate anyone on the origins of every bean that makes it’s way to Pammel Park and they can open up anyone’s pallet to a coffee world you may not have tasted before.


The town square of Madison is an historic one. Guess where this restaurant is located? Across from the northside of the courthouse! That’s me paying attention!
The high energy super food creations are in no shortage here. A generous portion of salmon over fresh greens, kale, cabbage, dried cranberries, sliced apples, sunflower seeds, shelled hemp seeds, chia seeds, flax seeds, and a side of orange-basil vinaigrette. That’s food fuel!
One of the best breaded pork tenderloins in the state and the folks at Northside Cafe aren’t afraid to tell you that.
The famous hot roast beef sandwich with plenty of gravy and mashed potatoes, and served wonderful hot.
The Caesar salad is fresh and they give you a healthy dose of chicken.
You want extra pickles? No problem. They have the hand patty express working in the kitchen to give you a supreme burger.
All behold the Buddha Bowl! Roasted broccoli, cauliflower, carrots, and chickpeas on quinoa with a Thai coconut curry. We had the option of chicken and devoured this healthy meal.

From comfort food to super food, Northside Cafe is creating the familiar and innovated dishes that many of us love. They are coming up with a special RAGBRAI menu with special high-carb and high-protein selections inspired by you, the rider. The site of something swimming in gravy is always an inviting one. This farm to table adventure will be open for 24 hours during RAGBRAI, so you have options literally all day and night in Winterset!

This was a hungry table of gallivanters and the Northside Cafe took care of all that! This was our table of guides for our entertaining visit to Madison County. From the head of the table working right is Ellen Wade, Linda Smith, Jared McDonald, and Sarah Reed!

Iowans love their local dairy bars and Winterset is no exception. This next Madison County icon is very easy to find when you catch yourself off the town square. I suggest you follow the crowd of both riders and locals to this next place.

This the Frostee treat you’ve been riding for!
Don’t call this a loose meat or maid-rite sandwich. Just ask for the beef burger and enjoy this town’s famous beefy masterpiece on a bun!
We love a big hug photo bomb and the ice cream counter behind the glass didn’t disappoint.
The time is now when it comes to recognizing the Pizza Burger as one of Iowa’s classic sandwiches. I won’t rest until this happens and Frostee’s is helping to make this happen.
And here’s the fun loving co-workers up close. People who enjoy their job have a way to make the food that much tastier.
The seasonal ice cream shop is known for having the famous fried cheese ball option and we take these staples seriously on The Iowa Gallivant
No matter what size of ice cream you order, the Frostee’s folks are going to fill it up full capacity!

Frostee’s is the go-to for the Winterset sweet tooth and famous sandwiches that people have been enjoying for decades. One thing we always say about towns we visit, is we always find reasons to keep coming back. The lunch break at Frostee’s is one of several reasons to head back to Winterset during your summertime road trips.

Directly on the town square and a Winterset treasure. The old fashion soda jerk is the refreshing way to step back in time during RAGBRAI.
Butter on everything, please. Double on my cinnamon roll!

When you have some supplies to pick up, make it a trip to Montross Pharmacy. And since you’re on RAGBRAI, get some of their homemade cinnamon rolls that the folks at the counter were talking up. Multiple people before and during our trip to Winterset told us that we had top by and we were happy we did.

Rest-up & Cool Down

The way we explored Winterset was a truly made historic by local historians, Linda Smith and Jared McDonald. If there is anything that Overnight #3 has is plenty of ways to take advantage of shady trees, air conditioning, and a break from the elements. And you can do all this by enjoying and supporting some of Iowa’s best local museums.


I wasn’t expecting what we would learn at the Iowa Quilt Museum. Before this day I recognized them as artistic barn decorations and precious family heirlooms for the most part. This place has another meaning. As you can see they have beautiful quilts on display and they eventually make it to our US veterans in honor of their service. Because of our Iowa travels, I have found a new appreciation for these thoughtful quilts.


The Madison County Historical Complex was very impressive. That is in no way enough of a description when it comes to this incredible collection of local history. There will always be something mind blowing when you visit these county museums and Winterset’s stands out with every turn, floor, and wall you encounter from the large piece of property it calls home. Stay tuned to The Iowa Gallivant because we’re going more in depth when it comes to this important museum.

If you know Iowa history, then you knew this one was coming for a Winterset trip! Welcome to the John Wayne Birthplace Museum!
The very long list of The Duke’s movies are forever etched onto the Winterset sidewalk. This is an amazing dedication by itself and we haven’t even made inside the museum yet!
Are you think what I’m thinking? You need some RAGBRAI souvenirs with one of the greatest actors in the universe’s history! When is the next time you’re going to back in Winterset? Get something from the gift shop and ship it back home or get those stocking stuffer ideas set. Did I just mention Christmas already?
Brian Downes is the executive director of this here museum, pilgrim. And he led me to what turned out to be my favorite display here. Paneling from the last scene of The Shootist, John Wayne’s last movie. I believe in the energy of certain places and this meant a lot to me. Come to Iowa for this one of a kind slice of history.
One of the main reasons why the blue collar culture loved John Wayne. He was very wealthy and stayed humbled his whole life. That meant owning a customized station wagon to drive around in. Yup. The car you picked up groceries in, drove to the Grand Canyon, and loaded up for baseball practice, is the same style The Duke enjoyed.
The actual buggy from one of his most popular and adored movies. Famous quotes from The Quiet Man popped in my head for the rest of the day after we were shown this in our private tour with Mr. Downes.
He did splurge a little and his yacht was just one of those luxurious items he loved. Only John Wayne would own a sea going vessel that the US Coast Guard would tie up to.
Replicas of famous guns from the Mr. Wayne’s iconic shootouts are in full and very shiny display.
From the days he was know as just Marion. Before his Hollywood created name of John Wayne, he was born here in the Morrison family. We learned that he liked his more iconic name much more. Marion Robert Morrison doesn’t scream out “sheriff of these parts.”
Ruth…. You have the floor! She has the knowledge of the birthplace home down as if she grew up in the house herself. These are the locals that make our travels so memorable. She was professional, educated, and kind, and all with a lot of spunk. You can tell that she loves and respects this house and you will too after hearing her interpretation.
The future John Wayne ate breakfast in this Winterset kitchen. Was he runny egg or scrambled kind of guy? I bet this facility’s talented group of guides could tell us.

The afternoon was spent looking for more of Winterset’s landmarks, history and places that many riders can enjoy and see for their own and possibly get some needed relaxation. All with that historical word again.

We realized that we were on the unofficial Dr. George Washington Carver trail during our scouting trips and Winterset was one of the towns he resided. In one of the alleys shaded by plush trees is this small park dedicated to the former resident of Winterset.
His inspiring story was a truly great American dream and Winterset has done a wonderful job of honoring Carver as the great man he was.
You may see the local Ben Franklin store owners walking the streets and watering the flowers that everywhere in Winterset and it goes with town pride you may feel yourself when you’re here.
You knew this was happening. The Bridges of Madison County have been the bread and butter of this area for many, many years. Its been a long time since they hosted RAGBRAI which means there’s thousands of riders prepping to see them again or for the first time.
Make the ride to Clark Tower and see the view of the river valley from one of the best vantage points in all of Winterset.
Even if you don’t make it to the John Wayne Birthplace Museum, you can still ride up and down his street.

Now, its time to really kick back and get some R&R at the Judge Lewis House Bed & Breakfast. If you’re looking for the farm-like atmosphere then let me direct you to our new friends, Mark and Kayla Hawkins who own this beautiful home.

Kayla was never too far away when we were enjoying this Madison County B&B. Wonderful hostess and with the genuine Iowa kindness and humor you want when you’re traveling to these scenic areas.
The second moment I knew I was going to love it here.
Hank was the official welcoming party and loves kids. Especially the big kid on the far right.

Kayla was absolutely awesome. Her attitude was one that encompasses the Midwest B&B culture and we loved every moment we spent at the Judge Lewis House. I stress that this is just a sample you’ll be getting of this B&B, because we’ll be bringing you an exclusive of this beautiful property down the road.

Each room decorated with its own charm and all with very comfortable beds. Blankets and quilts that make you feel that you’ve been coming here your whole life.
Kayla and I enjoying the parlor. As you can see it’s decor is perfectly matched with the small town setting it embraces.


They weren’t joking when it came to the chickens. Many chores to be done inside and outside of the Judge Lewis House.

From the moment of checking into this B&B to the time we had to say goodbye, we were swept up into positive energy felt here. Making your reservation at the Judge Lewis House is a good idea to have and RAGBRAI riders have done so as you can imagine. That’s not stopping the Hawkins’ from hosting some campers on their lawn. This shows that their hospitality extends to special events such as the one coming to town in July.

Hot Belgium style waffles with fresh strawberries, whipped cream, and bacon was the morning welcoming committee. A sidekick of endless coffee was close by.


You are about to see one of the most niche, artistic, and endless shops you will see on the entire route. This is the definition of re-purposed. This is 1st Avenue Collective.


Remember what the title said, right. This town is getting RAGBRAI ready!


The owners of the old Madison County Jailhouse turned 1st Avenue Collective have made it into a Winterset destination that handcrafted enthusiasts would adore. And not just them. Anyone seeking that perfect gift created by local artists and crafters.
Sandra makes unique jewelry you know that can find a good spot during your ride. They are even making specialized pieces made from old bicycle spokes. That’s dedication to the RAGBRAI legions!


Yes, this was hand made. Yes, they can ship this and other materials anywhere!


This is what I call vision. A true artistic wonderland of hand crafted gifts, jewelry, paintings, wine, cookware, cards, rugs, and A LOT more! They work hard with talented artists to bring you the inventory you see before you. And how’s this for a story! The dog you see is Luna and she was raised in a prison supplying therapy for its inmates. When adoption time came, Luna found a home in the jailhouse. She was so familiar with the settings she made herself at home under one of the cots. That’s a story you may never hear again. That is until you get to this jailhouse in Winterset.


Just outside of town is the next Iowa winery you need to know about. Best way to get to know them is by stopping in and making Covered Bridges Winery your new best friends during RAGBRAI.


A large and inviting tasting room that fills with countryside sunlight. Are you imagining your group making a long pit stop here yet?
This plate is 100% everything that I could eat everyday and not balk one bit. To be presented a charcuterie plate like this is about as close to a perfect afternoon I can think of.
And then Covered Bridges winery outdid themselves and finished off the presentation with a glass of LaCrescent and all the citrus notes you could want on a hot July day.
Needing something even more refreshing? Have that adult inspired slushy and get to cooling off in style.
Meet Kevin and Kevin! The masterminds behind Covered Bridges Winery!

Iowa wines are making a name for themselves in the wheelhouse of great and enjoyable varietals. Covered Bridges Winery hits all the right notes and they use 100% of their own grapes to make these wines shine. This is Iowa wine making at its finest. Let me take that further. This is wine making at its finest. The Hawkeye State grows many things in our vast agricultural industries. You can put a winery in Winterset on the list of hardworking growers that are coming up with a world class bottle of wine that’s going make your glass sing.

RAGBRAI Date Night

We’re back to the square and yet another historic building in Winterset. The Iowa Theater’s marquee is lit up year-round and we showed up on Way Back Wednesday!

The lure of the small town movie theater is gaining speed all over the state as many of them are renovating their facilities. The Iowa Theater has the state of the art systems that can rival any modern day cinema when it comes to the quality of your entertainment. You know what they don’t have here? Price gauging! Watch the video below and see why this place is where you need to travel to just for a movie. During RAGBRAI and all year long!

There is no hiding it. We were shown a slice of Winterset that seriously showed off some of the aspects of Madison County that could go overlooked. Would I travel here just for the movie theater? Yes. Just for the winery? Yes. Just for the county museum? Yes. Just for the B&B we stayed in? Yes. Just for the old jailhouse? YES! This all before we got to all those covered bridges I’ve heard about.

Thank you to Ellen Wade, Linda Smith and little Hazel for helping coordinate such a memorable trip to Madison County. You sure no how to pack in a huge amount of your proud city in just 24 hours!
Be sure to like RAGBRAI-Winterset on Facebook and see everything else Overnight #3 has to offer this July!
Be sure to like the RAGBRAI Facebook page to keep up on all the info for this year’s route!

You need to click here and bone-up on our coverage of RAGBRAI-2019!

We haven’t even told you about what we saw near Van Meter! stay tuned as we show one of Iowa’s bison herds VERY up close.

You need to click here and bone-up on our coverage of RAGBRAI-2019!

3 thoughts on “Scouting RAGBRAI-2019: Winterset’s History of Good Times is RAGBRAI-Ready

  1. Well done article! I’m from Winterset and haven’t been to all those places! Anxious to go now! There is another winery (Madison County Winery on the St. Charles road) and a beautiful Cidery (hard cider) just about a half mile north of the Covered Bridge Winery. Too much to see in a day.

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