Mount Hood’s Timberline Lodge is one of Oregon’s busiest tourist attractions in summer. It’s even more crowded during the winter ski season. Janell and I like to visit in November.

The weather is a magnificent gamble during Hood’s offseason. Once a blizzard buried our car. Sometimes rainstorms shake the building. Often there’s enough sunshine for the last hike of second summer. In November, rooms are always available at the lodge. Even at half price, they’re not cheap. But what a place to stay!

Timberline Lodge Credit: William L. Sullivan

The hotel began as a make-work project during the depths of the Great Depression. But by the time President Franklin D. Roosevelt dedicated this elegantly rustic hotel in 1937, it had become a grand expression of Northwest art.

As you drive up to Timberline Lodge from Government Camp, the forest dwindles to a few spindly firs and then gives way to tundra. When you reach the gray-shingled hotel you may well be above the clouds. Building anything at this elevation would be a challenge. Building a hotel was a monumental task.

Roosevelt had been looking for monumental tasks during the Great Depression. The hotel project employed 7,250 Northwest workers. As you climb the stone steps and enter the carved front door, you’ll see their labor-intensive handiwork everywhere. Ahead of you rises the massive hexagonal hearth, with three fireplaces on each floor. Its 92-foot-tall chimney required 400 tons of native stone. Look behind the fireplace to find a display about Timberline’s past.

As you walk up the stairs, run your hand over the banister’s carved animal figures — a sleeping bear, a beaver and an owl — polished by the hands of countless visitors. In the lobby, six massive ponderosa pine pillars support a gargantuan roof.

We brought teenage grandkids on our most recent November visit. They glanced at the colossal architecture and asked, “Where’s the pool?”

Timberline’s iconic weathervane motif was copied from a Camp Fire Girls handbook. Credit: William L. Sullivan

In fact, Timberline’s pool is reason enough to book a room. Completely rebuilt in 2024, the main pool is of modest size but the adjacent hot tub is enormous, surrounded by snowy trees and a panorama from Mount Hood to the Three Sisters. In that steamy bath you want it to snow, with flakes melting in your hair.

The kids swam themselves almost to sleep. In the morning I was able to lure them on a hike.

When Timberline Lodge opened in 1937, hiking trails were among the attractions devised to entertain guests. During the Depression, it wasn’t at all obvious that people would come to a fancy hotel on a mountain. 

St. Bernard dogs serve as tourist-friendly mascots. Credit: William L. Sullivan

And so, while the hotel was under construction, the Civilian Conservation Corps built the Timberline Trail, a 40-mile loop around Mount Hood. Realizing that most hikers would need five days to complete the circuit, the CCC crews built four small stone shelters along the route. The idea was that people hiking around the mountain might stay four nights in the huts, but that they would probably have to stay two nights at Timberline Lodge.

I took the kids on the easiest, most beautiful half-mile section of that trail, from the lodge to the White River Canyon. To find it, walk up past the right-hand side of the lodge on a service road for 0.1 miles. Then turn right on the Timberline Trail, which here is also the Pacific Crest Trail.

There is no sign, but the trail is lined with a row of rocks. The path crosses a gully filled with snow and then ambles out along a ridge beside a gigantic gorge with stunning views of Mount Hood. If you keep going you could circle Mount Hood — or end up in Mexico — but a viewpoint after half a mile is a good turnaround point.

This little hike was enough for my granddaughter Jasmine. She was ready to return to the pool. My grandson Brendan, however, wanted to climb Mount Hood. I diverted him to a more reasonable goal: the Silcox Hut, at the top of Timberline’s original Magic Mile chairlift.

The early managers of Timberline Lodge thought their guests might be convinced to go hiking in summer, but what could they do in winter? The answer was to install a mile-long ski chairlift — the first of its kind in America. Skiing was considered such a novelty at the time that the King of Norway was invited to come demonstrate the strange sport for Timberline guests.

The Silcox Hut is the stone building that served as the Magic Mile’s upper terminus from 1939 to 1962. Restored as a chalet in 1992, the hut now offers overnight bunks for groups of 12 to 20. It’s especially popular with wedding parties. If you rent the hut, Sno-Cats will haul your group a mile uphill from Timberline Lodge. A chef is sent along to prepare your meals. At 7,000 feet elevation, the place is a miniature Timberline Lodge, with a view to die for.

As you hike from Timberline up to the hut, you’ll meet people carrying snowboards and climbing gear. Mount Hood has become one of the most frequently climbed snow peaks in the world, and this is the most popular route to the summit. Hood has been scaled by a double amputee and a woman in high heels.

Klindt Vielbig trekked to the top in 1964 with a gibbon named Kandy. A typical ascent from Timberline to the summit takes seven hours, but Gary Leech set a still-unmatched record by dashing up in just 85 minutes.

When the Magic Mile chairlift opened in 1939, the Silcox Hut housed an engine and turnaround wheel. In those days, the single-passenger chairs crept uphill so slowly that the ride took 11 minutes. In 1962, the old lift was replaced by a double-seater a few hundred yards to the west. That lift was replaced in the 1990s by a high-speed lift with four-passenger chairs. Meanwhile the Silcox Hut became a snow-filled ruin, abandoned for decades. Finally a volunteer group restored it to its present splendor. They hired a blacksmith to forge chandeliers and replacement hardware in the Timberline tradition.

The Silcox Hut, a mile uphill from Timberline Lodge. Credit: William L. Sullivan

My grandson is 15. He marched up the old road to the Silcox Hut without puffing. Then he wanted to glissade back to Timberline. Actually, that wasn’t a bad idea. Just west of the hut is a gully that has snow all year. In winter machines fill it with snow and groom it into half-pipes for snowboarders. In November it’s a relatively safe chute for teenagers to boot-ski downhill a mile.

That afternoon the clouds hid the mountain and the temperature dropped. Tired from the day, the kids did homework by the lobby fire. They had seen Timberline’s fireplaces on TV. Every Christmas, a popular program on Oregon Public Broadcasting is a live video of the crackling hearth fire at Timberline. While kids tear open presents, families all over Oregon tune their TVs to the cozy fireplace.

When Christmas actually arrives, Timberline Lodge will be booked solid at peak season prices. The lobby will be packed with people clonking about in ski boots and snow gear.

If you want the place to yourself, do what Janell and I have learned works best: Risk the weird weather of November.

Portions of this column first appeared in William L. Sullivan’s 2014 book “Hiking Oregon’s History.”

William L. Sullivan is the author of 27 books, including “The Ship in the Ice” and the updated “100 Hikes” series for Oregon. Learn more: OregonHiking.com