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Winston County Gravel Cup had its inaugural event last year and is gearing up for round two. Through beautiful valleys and heroic gravel roads, the event carries an old cigarette branding theme and promises a full flavored event.

This year's event takes place on September 24, 2022 and has a 40, 60, and 100 mile option. Learn more about the event on their website or follow them on instagram. The event is organized by Paul Reardon , Jacob Ellefsen, and Luke Schuttenhelm

Interview with race coordinator, Jacob Ellefsen:

Let's start with the cigarette branding. What's that all about?

That is kind of what it has evolved into a bit. I must credit fellow ride organizer, Luke Schuttenhelm, with the creation of the ride’s name.

The race itself takes place in Winona and Houston County, so he mashed those together with some inspiration from days of NASCAR past and the Winston County Gravel Cup was born.

The cigarette portion is what grabbed people's attention, we even had an old Winston gas station sign show up on race day and gave away a ton of old Winston memorabilia.

It’s hard to take yourself too seriously with inspiration like that. Ultimately, we want riders to have fun. Whether racing at the front or beer stops every 20 miles.

We’ve made the route, but you make the ride.

This is your 2nd year, right? What were the highlights of year 1?

The biggest highlight for us was the overall success.

For year 1, we literally organized the ride in 4 months. No small task considering everything that goes into planning a ride, but at the end of the day it was all worth it.

Everyone finished safely and there was not one face without a smile.

Secondly, there was one rider that was a highlight for all those that rode with her… Nellie Rice, who embodied the very spirit of the event.

This was her first ever gravel event and on top of that, she chose the 100-mile route. Even showed up with fake cigarettes! She was so determined to finish, and it took her 10 hours and 52 minutes.

"She finished dead last but seeing that feeling of accomplishment on her face was an emotional moment for us as organizers. Riders like Nellie are really what makes all the time spent organizing the ride worth it."

What are the roads and gravel in "Winston County" like?

Well, when we don’t have the grader go through, they are the definition of hero gravel.

Last year unfortunately we had a stretch of road that was graded during the ride, but that’s just the way it is sometimes.

Luckily, everyone was able to find the humor about it

We are extremely fortunate to have such great roads to host the ride on. Pair that with the challenging climbs and spectacular views… It makes for quite an experience.

Why did you start this race?

We started this race to share the amazing riding that the Houston, MN area has to offer. The town itself exists in this weird space where it’s the destination for many riders from nearby La Crosse and it’s at the end of the Root River Trail when most riders turn back. It was really a well-kept secret for those that ventured out that way.

Secondly, we wanted to bring people together to enjoy and share in this rad experience and that’s the remarkable thing about the culture of gravel. In the end, everyone enjoys a beer together, whether they are racing for first place or simply trying to finish.

I see you have picked some charities to benefit. Why are those charities important to you?

We wanted to give back to the community that was so gracious to host us.

The Houston Nature Center and International Owl Center both provide great environmental education programs.

Additionally, the Houston Nature Center offers amazing amenities to cyclists such as showers and camping. Both locations are funded mostly by donations, and we wanted to help by donating to and promoting these community staples for our first year.




Plan a New Gravel Adventure

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