FREESKIERNewsAPR 23, 2026

Madison Rose and Jim Ryan to Host Superstar Showdown at Killington

On May 16, the Jim & Mads Show heads to Killington, Vermont to find the most diehard skier on the East Coast. Register today for the Superstar Showdown vertical challenge.

Superstar Showdown Killington Vermont

Featured Image: Courtesy of Killington Resort


Madison Rose Ostergren and Jim Ryan are heading to Killington, Vermont, in search of the most die-hard skier around. On May 16th, the Jim & Mads Show will be hosting the Superstar Showdown. The concept is simple: log the most vertical feet on the iconic Superstar run from 8 A.M. to 4:30 P.M., and you win. 

But it gets better. There's a $1,000 cash prize for the winning male and female rider, as well as a new pair of skis (or snowboard), prizes for both 15 and under and 60 and over divisions, plus awards for the best dressed. It goes without saying, but the champion will also receive unlimited bragging rights and dangerous amounts of pride.

You'll need to register for the event to participate, and there are only 150 spots available, so don't delay. There's a $10 registration fee, with all proceeds going to the Mount Holly Conservation Trust, which seeks to preserve and protect wild spaces around Vermont.

Killington Superstar Showdown

At its peak, the Superstar Chair offers 1,200 skiable vert, meaning you'll have to put your legs through an absolute gauntlet to secure the championship title. Will it be tough? Yes. Worth it? Without a doubt.

Even more so, as the pair will be filming an episode of the Jim & Mads Show during the event. The top finishers will likely get their shot at the big screen, and by big screen, we mean YouTube. If you've been searching for a spotlight to showcase a few righteous turns, this is your chance. Bring your friends and soak up the last few turns of the season in style at Killington.