This is episode 3 of a 5-part exclusive series, presented by Caldwell Collections and Matador Network. Learn more.

ARRIVING AT THE PARKING LOT on Thompson Pass felt like reaching the light at the end of a very long tunnel — after all, five days on the ALCAN Highway from Revelstoke is no small feat. Yancy and I pulled in late night in a sideways blizzard to the mountain pass we would call home for the next three weeks. We decided to come a week early to feel out the snow and lay some fresh tracks before the tailgating madness began. Emerging from the camper the next morning, I kept an eye on my brother’s face as his eyeballs widened, seeing snow-caked mountains rising 4,000 vertical feet straight from the parking lot. “H-o-l-y Shiiit,” he exclaimed.

Tailgate Alaska is held at the base of the Worthington Glacier, the closest possible parking to world-renowned powder turns. By means of touring gear, snowmobile, and helicopter, people of all walks of life migrate to Valdez, AK each spring to rip some classic Alaskan terrain on either side of the Richardson State Highway. Tailgate Alaska, now in it’s fifth year, has grown to almost 500 people from a small diehard crew of five guys dreaming big and not afraid to share the wealth. Weathering all conditions, meeting new people, enjoying the scenery/beer, learning about snow safety, and of course, getting into big lines, is what Tailgate is about.

With 3 heli operations within 15 miles, getting on the schedule for an unforgettable day is easy. For the more cost-efficient scenario, bring your snowmobile and you will not be disappointed with how many long pow laps you will log, sometimes when the heli can’t even fly.

Yancy and I met up with many good friends who’d made the pilgrimage to AK, and the good times started flowing, as did the free Alaskan Amber beer. You know you’re in the right place at the right time when seasoned big mountain riders tell you at the nightly bonfire that they just rode the best spine or chute run of their entire life. Powder is usually plentiful, but beware of waking to boiler plate backside turns the next morning — the wind can howl across the Chugach! Even with 500 people, though, the Alaskan terrain is so vast and abundant that the thought of it getting tracked out is not a concern.

After five days of bluebird powder, another storm rolled in to hit the reset button just in time for the “King of the Hill” Freeride World Championship event, put on by Tailgate Alaska. Low and behold, I picked a technical line to ride that had sheltered powder inside a nook on Python Peak, rode it clean, and took home the championship title and samurai sword. I was stoked that my peers voted my line as the winning run, as it always feels good to come out victorious knowing your fellow riders approved.

Our crew awoke each morning not knowing what the winter wonderland of the Chugach Mountains would bring. But as all good things must come to an end, the Tailgate lot dispersed in a flurry as another heavy storm socked in…and another legendary Alaskan event was about to unfold a short 160 miles to the north. The energy of Arctic Man was calling, and good friend Nate Holland promised powder in the Hoodoo Mountains.

Words and photos by Wyatt Caldwell; video by Yancy Caldwell.

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Home sweet home. Not a bad place to park for three weeks...that is, if you don't mind the sound of helicopters and snowmobiles every morning.


Here's a view of the famous zone called "The Books" due to its bookshelf-style ramps. It's a risky 16-mile sled ride each way...better not get caught in the quick-building fog.


Sledding in Alaska is humbling to say the least. Vast mountains present dangerous crevasses, meaning picking the right route of travel is a must in order to access the goods.


Yancy getting his mind blown 3,000 feet to the valley floor, in an area known as Loveland.


The harbor at Valdez has some classic maritime history, as evidenced by a graveyard of ships lining the marina. If wrecks could talk, these would have some tales to tell. The Kingfisher is only taking the winter off, and will return to the water after the spring snow melt.


A day out with H20 heli was part of the "King of the Hill" Freeride World Tour. "Just another run in the Chugach."


Yancy amping on his super loose run down the Tiger's Penis spine. His first AK heli run!


Yancy and I pause to shoot a time-lapse and take a breather after hiking Python Peak, behind us.


The evening light creeps up the Python as we race to hike the ridge at sunset. Feeling lucky to be in the right place at the right time.


I managed to take home the W and the samurai sword along with women's champ and Japanese ripper Yoko Nakamura.