Baxter Cochennet of Heelclickers Photography

The Winston County Gravel Cup

Whether you choose the 20-, 40-, 60-, or 100-mile route, you will not be disappointed with the unique experience this ride will provide. Mainly gravel, with only a touch of pavement, you will travel through wooded lanes, challenging climbs, and open valleys to discover this area's incredible views.

This ride is whatever you make of it... Whether you choose to set a personal record or a personal goal to finish, all riders of all skill levels are welcome to join us on September 23rd. If you want to race, go nuts. We will be timing the event. If you want to go for a fantastic ride with friends, go nuts. This is about having a good time.

Unfortunately, we aren't offering refunds for this event. 

General Rules:

  • You are in charge of yourself. 100%! This is an unsupported ride.
  • You must register for the event. You will be added to the list. The list will be posted.
  • Everyone must wear a helmet.
  • Be prepared for anything. Weather. Mechanical issues. Hydration. Food.
  • Keep the course clean. LEAVE NO TRACE.
  • Be respectful and uphold all traffic laws. Communicate with other riders. Ride safely and use good judgment.
  • We are here to have fun, don't be an asshole. This event is put on by volunteers, who donated time and money. Be nice to them. Be courteous to all other road users (Cars, Trucks, ATV, and Tractors).






New for 2024, hoping to get more people on bikes. Riders can expect fewer elevation gains which means fewer hills but with the same great views.
11 am start
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40 - LIGHT

Our most popular route last year. The majority of it is on gravel roads, touching pavement only in a few sections. Over 2,000 feet in elevation gain throughout this route. Even if this is your first gravel adventure or a seasoned gravel racer, this route gives each rider a Minnesota Nice mix of what the Winston is all about. This route consists of two major climbs and two descents. The beautiful Perkins Valley descent is breathtaking as you work your way to the finish line.
10 am start
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60 - MILD

The sweet spot. This route shares many of the same roads as the 40 route. We do throw in an additional descent and major climb on the 60. Over 4,000 feet in elevation gain throughout this route. Expect to turn up the endurance for this one compared to the 40.
9 am start
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The Winston County Gravel Cup, the big boy. Over 6,000 feet in elevation gain throughout this route. This route shares many of the same roads as the 40 and 60 routes. Expect a few more difficult climbs for this one, the 100 route will test your endurance abilities. Expect to be on the bike most of the day, be prepared. Challenge accepted?
7 am start
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