Like most kids who grew up in the '90s, I watched Nickelodeon until my eyes were bloodshot. I was naturally obsessed with classics like Doug and The Adventures of Pete & Pete, but the one show I didn't expect to capture my attention was Wild & Crazy Kids. The skateboarding and surfing scenes in this reality program, where children competed in physical challenges, were cool enough on their own, but the true jaw-dropper to an 8-year-old Ohioan had to have been the snowboarding. I grew up in the middle of the snow belt, and until that point the concept of shredding a mountain in a fluorescent Body Glove T-shirt with the sun shining was entirely foreign to me. Where was this place where everyone was tan and blissfully unprepared for the elements?

The answer: Big Bear Mountain in Southern California.

“California is for surfers,” I thought to myself as I looked at a map. Then a light bulb went on. What if somebody tried to snowboard and surf in the same day? I shelved the idea and moved through my life wondering if it would ever be possible. Then I moved to Oregon in 2013 and visited Mount Hood on a hot day that summer, shocked to see Timberline still crawling with skiers and snowboarders and knew this was the place to give it a shot. Two years later, I learned to surf and memorized every twist and turn of the 150-mile stretch of Highway 26 between the mountain and the ocean.

If you time it right, hitting Timberline Lodge and Ski Area (27500 E Timberline Road, Government Camp, 503-272-3311, timberlinelodge.com) in the morning and a popular surf spot like Short Sands Beach or Indian Beach near Cannon Beach in the afternoon is a breeze. I did just that in early April, and the following itinerary is a good way to enjoy both spots with minimal snags (traffic, refueling) along the way.

8:30 pm the night before: Anyone who’s been to a real ski resort like Aspen or Tahoe knows that Government Camp, Mount Hood’s de facto ski village, is a charming shantytown in comparison. The upside of that is lax enforcement of car-camping rules, which means parking and crashing overnight to get a jump on snowboarding the next day is easy. Head up the hill past most of the businesses in the middle of Government Camp, find a cluster of crusty old vans obviously on the same mission and drop anchor.

10 pm the night before: Walk to Charlie’s Mountain View for a few tallboys of Rainier and some spirited conversation with the locals.

8:15 am: Roll through High Mountain Cafe for a breakfast burrito and coffee. As the only quick, early morning meal option in town, it has perfected the art of serving massive portions to hungover dirtbags who spent the previous night in their vehicles.

9 am: Purchase a lift pass and take the first chair up from Timberline. It wasn’t quite the bluebird day I’d hoped for on my visit, but all of the lifts were running. For plebs like me who’d rather be derping around the woods on West Leg rather than going all the way up to Palmer Glacier, this was a huge bonus. I’ll take fat, wet snowflakes over bone-dry conditions and bombing the glacier under a blinding sun any day. But if you’re stoked to ski or snowboard on the Fourth of July, it’s amazing this option exists and definitely helps make Oregon such a magical place.

12:15 pm: Snowfall turned into rain, and it was time to pack up. Per the advice of Martin Schoeneborn, co-owner of Up North Surf Club, I checked the SwellInfo app for that afternoon’s surf conditions. Short Sands was projected to have another set of solid waves rolling late that day, but the hike in and overload of tourists made it a questionable bet for such a compressed schedule. Ultimately, your goal is to get off the mountain and into the water before the tide is out and the sun goes down. I opted for Indian Beach instead, which was forecast to have slightly smaller, choppier waves, but it promised to be a quicker trip with less tromping through the woods.

12:45 pm: I stopped in Welches for a beer and an avocado and turkey wrap at Wraptitude, a quaint little hippie cafe that’s decked out in decades-old Burton and Dakine ads, prop snowboards bearing Budweiser and Corona logos, and a fake thatched roof that slopes over the bar.

2 pm: Traffic from drivers merging on and off of Interstate 405 north and Highway 26 near downtown was already backed up all the way to the Southwest 4th Avenue exit. Welcome (back) to Portland!

3:45 pm: I finally made it to Indian Beach. It was cold, overcast and windy, which was almost exactly what I expected. A few couples in sweats wandered around the parking lot, taking selfies with the craggy edge of the coast in the background and jumping back in their cars. A guy in a truck with Idaho plates stopped to ask, “What’s wrong with you?” as I wriggled into my suit. I told him about my grandiose dream to snowboard and surf on the same day, and he wished me luck with a sidelong glance. I expected him to drive off, but he sat there idling for a few more minutes. This was not the vibe I needed before diving face first into 50-degree salt water.

4 pm: I stood on the beach, board in hand, and considered the stupidity of this adventure. The waves were a violent torrent of knee-high whitecaps, with very few clean breaks in sight. I saw a rideable wave in the distance, maybe 15 yards into the ocean, but swimming out there was certain to be a huge pain in the ass. I didn’t come all that way to succumb to adversity, though, so I plopped my board into the shallow water and started paddling.

4:30 pm: I finally made it to a calmer spot past the break. But trying to ride back to shore was difficult. With each attempt, the swells were quickly subsumed by rough water near the shore. If I were a more competitive person, not catching a wave on this day would’ve been a real bummer. But I’m not that kind of person. I head in.

Appreciating the effort rather than getting hung up on achievement is an innately Oregon trait. Though I’ve often felt like a carpetbagger in the six years I’ve lived in this wonderful state, being able to smile at the memory of shivering in the chaotic waters of the Pacific Ocean is something I’ll always cherish. All in one day, I snowboarded, surfed and immersed myself in the epic scenery of Highway 26—a feat not possible in most other places.