Story & Photos // Jake Sullivan
December 21, 2025
Ever since Killington announced its decision to break away from POWDR Corp and become independent, rumors about the return of Rails 2 Riches have been circulating town. For years, some of the biggest names in East Coast snowboarding gathered under the lights at the bottom of Highline - in the shadow of Killington Peak - putting it all on the line in hopes of securing a giant check just before the holidays. Rails 2 Riches was more than just a rail jam; it was a rite of passage for many snowboarders.
At times, it felt like we were getting a firsthand look at the future of our sport. Nineteen years ago, nearly to the day of this article, Lucas Magoon won the second annual Rails 2 Riches. This marked the beginning of one of the most dominant rail jam careers in snowboarding history. I don’t recall many details about that event. What I do remember, though, is that there were almost as many people at my apartment in Rutland for the after-party as there were at the rail jam that night. Random people were showing up to our house, just for a chance to hang out with the 17-year-old prodigy, now known as Gooner.
Lucas Magoon and Niko Cioffi - Rails 2 Riches 2006
Our culture thrives on moments like these. Years later, we will remember a cold night when we watched in awe as an unknown snowboarder completely took over an event. We will proudly say we were there the night “so-and-so” made their mark on our world. However, as Rails 2 Riches faded away—lost in the shuffle of corporate restructuring and changes in ownership—it felt like there was a void in our local scene that might never be filled again.
Connor Kelly - Switch Front Board
A lot of us were skeptical when we first heard about Killington’s plan for Deck The Rails. “Why not just bring back Rails 2 Riches?” was a common theme I heard on barroom stools and in snowboard tuning shops. But as details rolled in, and news of the $20k cash purse moved from rumors to reality, the tone quickly changed.
Rosey and Garceau - Crowd Hype Kings
And let's be honest: events are only as strong as the people behind them. The moment I heard that longtime Darkside collaborator Mike Garceau would be hands-on with Deck the Rails, any skepticism I had disappeared. While Garceau didn’t create Rails 2 Riches, he took it and transformed it into the marquee East Coast event it became. Last night’s Deck the Rails felt just as impressive. Throughout the day, I kept thinking, “Killington is so back.”
True to form, a day before the event, we experienced torrential rain followed by a nearly 30° drop in temperature, giving the KParks crew anything but ideal conditions during the event build. But as they always do, the team powered through the brutal weather and provided a setup that further echoed the legitimacy of the rail jam. Multiple lines, a wall ride, a crazy tube to dfd combo - the setup was big, unique, and worthy of such a large cash purse. Shoutout Park Crew for doing such an excellent job.
Cali Carlson - Front Board
Darkside’s crew came out in force for the event. Gomez, Cali, Fern, Connor Cav, Connor Kelly, Hagen, and the newest addition to the squad, Austin Esposito, threw down all day during qualifiers and all made it into the finals. KSA General Jay “Rosey” Rosenbaum was on the mic alongside Garceau, both of whom were hyping up the crowd and running a proper show.
Newest Darkside Team Rider Austin Esposito
Gomez - Layback Front Board
Some standout moments were - Fern ollieing off the kink rail lip over the fence and out of the venue, Gomez reminding everyone that style is still the most important part of snowboarding, Connor Cav taking a few of the hardest slams of the day and getting up like it was nothing, Austin lacing tricks so casually on the waterfall rail that he made it look like a flat bar, and Connor Kelly putting on a clinic doing some of the heaviest tricks and gaps the setup would allow. In the end, Gomez and Fern tied for 3rd, Austin landed in 2nd, and Connor Kelly won his second rail jam in 7 days with an undisputed first-place finish. On the women’s side, Cali held it down for the second weekend in a row, lacing heavy tricks on every feature and finishing in 2nd.
When the judges can ride as well as these three, you'd better be on point.
It was a huge night for the Darkside crew. Thanks to everyone involved in the event. Shout out to Tucker, Ryan and Joey for judging what had to be one of the most difficult finals to call in recent memory. Garceau and Rosey for keeping the long day entertaining and exciting. And, last but not least, Park Crew, KMS, and Killington Events staff for hosting such a fun contest. As for the return of Rails 2 Riches? We don’t have any idea yet, but we do know we can’t wait for next year’s Deck The Rails!
Deck The Rails 2025 Photo Gallery
