Portland’s Worst Day of the Year Ride & More Winter Fun

Night skiing at Mt. Hood Skibowl—sometimes in the shadow of fireworks—is a popular activity with Portland-area thrill-seekers.
Night skiing at Mt. Hood Skibowl—sometimes in the shadow of fireworks—is a popular activity with Portland-area thrill-seekers. Mt. Hood Territory
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This time last year, Oregonians collectively wondered where all the snow went. Temperatures around Portland rarely dipped below freezing, ski resorts reported snowpack levels far below average, and scattered rain showers were about the only precipitation most of us saw in early 2015.

Fortunately, 2016 is off to a more promising start for winter sports enthusiasts. Thanks to colder temperatures and heavier precipitation, all of Oregon is enjoying far more snow than at this point last season. The question on Mount Hood is no longer, “Which lifts are open?” Rather, it’s, “How many runs can I fit in today?”

But enjoying winter in Portland isn’t exclusively reserved for the ski resorts: The snow also brings a proverbial avalanche of adrenaline-pumping fun that can be found far from the slopes. Do you want to ride fat bikes through snow-capped peaks near Bend? Explore the Mount Hood backcountry on a splitboard? Test your mettle in bone-chilling water? These ideas should provide excellent inspiration for winter adventures in Portland.

1. Take the (Polar) Plunge.

Polar Plunge events have become popular winter festivals throughout the United States and Canada in recent years. Special Olympics BC

Polar Plunge events, in recent years, have become fun, frigid ways to raise money for important causes. Brave souls can join the fun locally when the frosty fundraiser takes place on February 27 in Portland. Portland’s Polar Plunge will raise money for Special Olympics Oregon.

Participants will wade, run, jump, walk, and crawl into the Columbia River at Broughton Beach, near Portland International Airport, where water temperatures aren’t expected to top 40 degrees.

But there’s more to the Polar Plunge than a quick, icy dip. Would-be participants must raise at least $50 for Special Olympics Oregon before taking the plunge, and registration includes a long-sleeve T-shirt, bowl of soup, and a beach party that includes live music, food, and activities. Athletes looking to up the ante can walk or run a 5K before plunging, as well.

2. Go for a snowy spin on a fat bike.

Fat biking has become an increasingly popular winter pastime in Central Oregon in recent years. Jereme Rauckman

Given its reputation as one of the country’s best year-round outdoor adventure hubs, it’s no surprise that Central Oregon hosts a handful of outstanding fat biking trails. Newbies can tackle the Tumalo Falls trail for a relaxing ride with a nice payoff, but Dutchman Flat, adjacent to Mount Bachelor, promises an all-day experience for more adventurous riders. The sno-park provides 19 miles of cross-country ski trails and 150 miles of groomed snowmobiling routes, giving riders plenty of room to play while enjoying stellar views of Bachelor, Tumalo Mountain, and more.

3. Give splitboarding a shot.

Splitboards can be taken apart to form ski-like parts (useful for ascending slopes); they are then reattached and can be used as snowboards for the trip down. donchili

Can’t decide between skiing or snowboarding? Luckily, you don’t have to: Splitboarding combines cross-country skiing with snowboarding to give adventurers the freedom to explore backcountry forests and remote wildernesses. On the way out, boarders use two ski-like halves of a detachable snowboard to ascend a slope or trail; at that point, they reassemble the board and snowboard back down.

Luckily, nearby Cascade volcanoes (including Mount Hood and Mount Rainier) provide plenty of outings for aspiring splitboarders. It’s not without risks—boarders should be familiar with their backcountry surroundings and undergo avalanche training before heading to the mountain—but for some, it means seeing unusual terrain far from crowds.

4. Get outside on the Worst Days of the Year.

The Worst Day of the Year Ride takes cyclists—many of them costumed—throughout Portland. Good Sport Promotion

The Worst Day of the Year Ride fits well within the “Keep Portland Weird” motto: While the rest of Portland stays warm and snuggled up with their sweethearts inside, thousands of cyclists don costumes, ride around town, and enjoy a post-ride beer at a local brewpub. (Fun fact: While it was initially scheduled in February to reflect Portland’s cold, wet, and rainy winters—inspiring the name of the event, referring to the nasty weather—the ride usually lucks out with mild temperatures and minimal rainfall, other than when snow and ice shut down the city and forced a cancellation in 2014.)

Cyclists can choose from two courses, both of which start at Lucky Lab’s brewpub on Southeast Hawthorne Boulevard: The 15-mile urban course heads into Northeast and North Portland before returning to the inner Southeast brewpub. The 42-mile Challenge Course, on the other hand, follows the urban course through Northeast and North Portland before crossing the St. Johns Bridge, tackling the West Hills, and turning back toward town in Hillsboro.

Not to be outdone, the Worst Day of the Year Run encourages runners and walkers to brave the elements, don costumes, and check out the gorgeous Edgefield grounds (part of the regional McMenamins empire)—all in early February (Feb. 6, to be exact).

Runners or walkers will tackle two, 1.55-mile laps on packed gravel around Edgefield’s golf course, making a complete 5k. The route features views of the nearby Columbia River, and registration includes a custom finisher medal, free beer for costumed participants, homemade soup from McMenamins, an indoor post-race party, and more.

5. Go night skiing.

Night skiing at Mt. Hood Skibowl is a popular wintertime activity among Portlanders. Mt. Hood Territory

Want to watch the sunset over a wintery horizon in Portland? Stargaze from Oregon’s most iconic mountain? With a handful of night skiing options on Mount Hood—and suitable snowpack—now you can.

Mt. Hood Skibowl is perhaps the most popular night skiing destination among Portlanders. Home to nearly 1,000 acres of terrain, Skibowl hosts what it calls the largest night skiing area in the United States: Thirty-four lift runs have lighting and remain open until 10 or 11 pm nightly, giving skiers and snowboarders the chance to traverse the wooded areas in a whole new way.

A couple of other spots also let night owls get their skiing fix. Mt. Hood Meadows offers 140 acres of night skiing Wednesday through Sunday, and Timberline Lodge remains open late on Friday and Saturday evenings.

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