You Could Win $1,000 For Skiing All Day at This Vermont Resort
Ever wanted to earn cash and ski your heart out?
Killington, Vermont, has just the thing for you. On May 16, 2026, the ski resort is hosting The Superstar Showdown, a bell-to-bell "downhill endurance event."
The premise is straightforward. The man and woman who ski the most vertical on the famed Superstar Glacier take home $1,000, plus a new pair of skis or a snowboard. Prizes for 15 and under, 60 and over, and best dressed are also on offer.
The entrance fee is $10. All proceeds go to the Mount Holly Conservation Trust, an organization dedicated to preserving the character of Mount Holly.
What's more, Killington's hosting the event alongside Madison Ostergren and Jim Ryan, two of skiing's best-known rippers. If anyone's mastered skiing bell-to-bell, it's them.
Here's their pitch.
The 2026 POWDER Photo Annual is here! Look for a print copy on a newsstand near you, or click here to have a copy shipped directly to your front door.
https://www.youtube.com/shorts/9S_WNh3uHDQ
Ostergren and Ryan won't just be attending. They plan to film an episode of their web series, the Jim & Mads Show, too. Previous outings include high alpine excursions and skijoring.
So, you might get a cameo if you show up.
More importantly, though, you'll get to see the duo ski in person. Earlier this year, POWDER caught them in action at the Sun Valley Stampede and let me tell you: Ostergren and Ryan can ski like nobody's business. I'm not sure I knew what carving was until I caught them blitzing down the Stampede course.
For Killington, the Superstar Showdown reaffirms the resort's status as one of the Northeast's best-known springtime haunts. Killington's season regularly extends into May or even June. The Superstar trail has long been the hub of this late-season activity, so it only makes sense to host an event there.
"From first chair to last, we're in for a day-long showdown on the infamous Superstar Glacier," the description for the Superstar showdown reads. "Only the strongest will make it bell to bell and earn the title of Superstar Showdown Champion."
If you think you have what it takes, you can head over to Killington's website and register.
Related: My Quest for the Ultimate Ski Boot Nearly Ruined Skiing for Me
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This story was originally published April 22, 2026 at 6:14 AM.