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