Plan a Perfect Day at the Mountain

Mount Hood is made for wintry thrills—and relaxation. Just follow our five-step route to alpine bliss.

1. Spend the day frolicking about at Skibowl, where 65 runs, a vertical drop of 1,500 feet, and the most black-diamond runs of any resort in Oregon draw enthusiasts on the hunt for untouched powder stashes.

2. When those quads begin to burn (believe us: they will), drop into Skibowl’s midmountain Warming Hut, where the remedy for your pain lies in a Spaten Optimator, sipped by the stone fireplace along with a bowl of steaming Hungarian goulash. 

3. Repair to Timberline Lodge, Oregon’s Cascadian masterpiece of soaring lobbies, brawny beams of Douglas fir, and towering stone fireplaces. Take your pick between a hostel-style bunk room, a private corner room, or a “fireplace guest room,” where Timberline’s aesthetic shines with handcrafted rugs and stone hearths. From $125/night.

4. Once you’re settled, order yourself a hot buttered rum and get thee to the roomy outdoor hot tub, where you can watch the evening flakes fall as silence settles over the mountain.

5. Come nightfall, set forth on a moonlight snowshoe tour with Mt Hood Adventure, on which an expert will lead you on a trek for up to six miles through snow-blanketed terrain, guided only by Hood’s alpenglow and the twinkling stars.

Glide Silently Through Oregon’s Wilderness

Ever since 19th-century miners first strapped 12-foot wood planks to their feet, cross-country skiing has been the way to travel through the Northwest in winter. For beginners and Olympic biathletes alike, we scouted the best spots to shuffle and skate your way through Oregon and Washington’s snowy forests, mountains, and meadows. 

Teacup Lake

On wide trails groomed three to four times a week, cruise flat beginner loops from 1 to 8 kilometers, zip down Wahoo Gulch, or prove your Nordic chops by marching 4,000 feet up the 1 km Screamer Hill, until Hood’s peak feels close enough to touch. Access: Park at Teacup Lake Sno-Park off Highway 35. Sno-Park permit required.

White River

Away from the crowds, climb a gentle 800-foot slope through the piney forest alongside White River, pausing to savor views of the White River Glacier as you journey beneath its shadow. Cruise back along the open snow beside the river.  Access: Past Government Camp on Highway 26, take the Highway 35 to White River West Sno-Park. 

Old Man Pass

Unlock Washington’s primitive trails in the shadow of Mount St. Helens. Near Indian Heaven Wilderness, meander through a dense forest on the 7.4 km loop, burn through the 16.4 km Hard Time (despite the name, this trail is relatively flat, and offers unforgettable views), or link Trails 157 and 159 for the ultimate challenge, a 15 km uphill trek past striking views of St. Helens. Access: Take State Route 14 to the Wind River Highway to a junction with Forest Road 3055. Washington State Sno-Park pass required. 

Worship the Sun on the Klickitat Trail

In Chinook, Klickitat means “beyond.” That’s your first clue that this rails-to-trails path in Lyle, Washington—on the dry, eastern side of the Gorge and only an hour and a half from Portland— offers an escape from sopping winter rains. It’s also gorgeous. Stretching 31 miles, the route wanders among rugged canyons and valleys of the Columbia Hills where perky wildflower displays arrive by February. The first few miles provide the perfect introduction, with close-up views of the wild and scenic Klickitat River, where winter runs of chinook salmon (and mild weather) draw flocks of sunbathing bald eagles. Access: State Route 14, just west of SR 142, in Lyle, Washington 

Play House for the Weekend on Mount Hood

When wanderlust extends beyond the chairlift, head for one of these overnights. 

Snow Bunny: Less than an hour from Portland sits the Swedish Stuga—a local version of the cottage that’s an emblem of Scandinavian relaxation—surrounded by acres of forest. Within its red clapboard walls (made with eco-friendly materials), you’ll find Nordic-inspired luxury in the form of old-growth Douglas fir floors, an antique wood-burning stove, and a big claw-foot bathtub. Beyond a footbridge, acres of private land peppered with trails and miles of Mt Hood National Forest await. From $150/night 

Cross Countryman: Oregon and Washington boast more than 50 recreational rentals. These cabins and lookout towers—aka alpine tree houses—come with all the essentials: mattresses, woodstoves, solar-powered lights. Some require a trek via snowshoe, but the payoff is worth it. The view from atop Clear Lake Butte lookout, for example, boasts unobstructed degrees of Timothy Lake and miles of snow-dusted Douglas firs with Mount Hood’s craggy summit looming in the distance. From $30/night, fs.fed.us

Nanook: Self-guided tour outfit Cascade Huts’off-road bike routes transform in winter into miles of snowshoe and backcountry ski routes. Three minimalist lean-tos, loaded with propane heaters, kitchen supplies, and zero-degree sleeping bags, are your respite from the blustery climate at 4,000 feet. An easy trek to the first hut is perfect for beginners, while experienced backcountry skiers can plan their own routes with GPS coordinates from the Cascade Huts team. $150/night, cascadehuts.com

Outfit Yourself for the Soggy Glory of Winter Biking

For cyclists, winter separates the women and men from the girls and boys. Wet. Dark. Cold. In a word, fantastic. Glossy asphalt and the perfect excuse for a brandy beckon. A good jacket goes a long way. So for the glorious, character-building months, consider upper-body options with Portland connections and not too much sweat-inducing bulk:

• Nau: The Hokkaido Blazer (men, $475) makes stately wool waterproof with blended nylon and spandex. The Tripoly Hood (women, $268) combines recycled polyester and organic cotton and includes a snap-off hood.
• Showers Pass: The Amsterdam Jacket(men, $200) comes fleece-lined and herringbone-patterned, perfect for a chic commute. The Rogue Hoodie’s (women, $160) three waterproof layers mean you usually need only a T-shirt underneath.
• Rapha: The Women’s Rain Bomber ($390) offers snazzy tailoring and reflective details for those dark rides home. The Hooded Rain Jacket(men, $390) features a hood that can be rolled away and fastened in the collar.

Stop Grousing About the Weather and Get Outta Town

There is this strange and wonderful place in Portland called an airport. They even nicknamed the city after it: PDX. Consider it a magical transporter machine, like the one on Star Trek, only real and staffed by folks eager to scan your body and carry-ons. With 240 flights departing daily, slipping off to beat Stumptown’s gray-sky blues is as easy as 1-2-3. Trust me: I’m a flying fanatic who’s logged 100,000-plus air miles annually for years. Here are some of my go-to winter getaways:

1. PALM SPRINGS After a long cultural drought, this storied desert sun spot is hip again. Downtown shopping action is still best along North Palm Canyon Boulevard. The venerable Sherman’s Deli remains a popular nosh stop. Best of all, it’s just a quick two-and-a-half-hour hop away on the daily Alaska Airlines nonstop flight. 

2. BOSTON Nostalgic for real winter weather? Try a Nor’easter with a foot of snow and subzero temps. In the Back Bay, I shop hard on Newbury Street then hunker down at The Lenox near Copley Square, a slightly tatty tourist favorite, or, if I’m feeling flush, the Mandarin Oriental. Lunch at Neptune Oyster Bar in the North End is a must, followed by cannoli at Mike’s or Modern on Hanover Street. 

3. ARUBA As a determined sun worshipper and frequent-flier-miles accumulator, I’m fine with the 12-hour, multi-segment trip on American or Delta Airlines to spend a long weekend in the southern Caribbean sun—and earn close to 10,000 miles for my trouble. You can’t go any farther without running smack-dab into Venezuela. There’s a new Ritz-Carlton along the exquisite white sand Palm Beach. In nearby Noord, I love Café 080 for Dutch snack food. And Dr. Coco’s brightly decorated cart is a mandatory stop near the airport for fresh-from-the-source coconut water.