It’s the night before we are supposed to hit the Timberline Trail, and the forecast is not good.

What a week before had been nothing but sun and blue and calm has all of a sudden whipped into a red flag warning for the western Cascades: dry, fire-prone conditions, no rain in sight and winds gusting up to 50 miles per hour. All the requisite agencies are pleading for people to stay out of the mountains. Prospective hikers are bailing on their trips, sharing their postponements on Facebook.

The four of us – myself, Will Armistead, Chris Gomez and Ryan Odegaard – already had to bail on this trip last year when early snow threatened to derail us. We have the time off now. We’ve done the training we’re going to do. We’re supposed to start at Timberline Lodge and head west, away from the worst winds for the first day.

And so we decide to go.

Despite the bowing trees and bending grass on the way up to the mountain, the unnatural hum of the generators powering the lodge – the power companies had killed the electricity to reduce the risk of fire – and the absolute ghost town that greeted us at Timberline on a day that normally would have been bustling, it was the right decision.

We set out just after 9:30 a.m. It was windy, sure, and there was a bit of tension in the air. But the trail, which runs 42 miles around Mt. Hood and includes some 10,000 feet of elevation gain, starts out easy. The wind was at our backs. And not 45 minutes into it, after we’d first cross paths with a friendly foursome who we’d leapfrog with over the next four days, it was still and peaceful. Red flag warning? Never heard of it.

As can happen on the Timberline Trail though – this was my third time doing it – we ran into other challenges that would pose their own obstacles. Gomez got some kind of stomach bug that chose to ride along with him from the second morning on. Some blisters set in and a few knees ached. The bugs were not insufferable, but they were annoying. The climb up from Ramona Falls to Bald Mountain was crushing; the one up from Cloud Cap to the trail’s high point near Gnarl Ridge just brutal.

But along with the struggles comes the glory that accompanies taking in Mt. Hood from all 42 miles of the Timberline Trail: the drop down into Zigzag Canyon, the side slog up to Paradise Park – which reminded me of my old friend, Oliver, and a gorgeous trip we had up there – Ramona Falls, Elk Cove, the coast down Gnarl Ridge, the final relief of the pavement and the cold beers in the lot at Timberline Lodge at the end of day four.

The Timberline Trail. Never the same trail twice. Always an epic adventure.