Solo on the Timberline Trail

The Timberline Trail around Mt. Hood spans just over 40 miles—specifically 42 miles—with a cumulative elevation gain of about 8,000 feet. At the beginning of 2024, I decided this would be my big physical achievement for the year, and I committed to tackling it solo. Kaylyn appreciated the ambition but decided that three days and two nights on the trail, living out of a backpack, wasn’t quite her ideal weekend—understandably so!

My pack weighed in at about 35 pounds, filled with everything I’d need for three days of hiking, including food and essentials. Kaylyn dropped me off at Timberline Lodge at 7:00 a.m., and with a mix of excitement and nerves, I set off on the trail counterclockwise. The morning greeted me with fierce winds that tested my resolve right from the start. By nightfall, thundershowers rolled in, adding a dramatic flair to my first night on the trail. Despite the elements, I remained undeterred—there’s a certain thrill in embracing the unpredictability of nature.

The landscape around Mt. Hood is nothing short of breathtaking. Rugged ridgelines, lush alpine meadows, and glacial river crossings kept my senses engaged, my spirit uplifted, and my thirst quenched. Each turn of the trail offered a new vista, a reminder of why I love spending time in the wilderness. Hiking solo gave me the space to reflect, think critically about my approach to challenges, and truly connect with the environment around me.

Mindfulness became a key part of the journey. Without the distractions of everyday life, I found myself attuned to the subtle sounds of the forest, the changing light as the sun moved across the sky, and the rhythm of my own footsteps. I was reminded of the value of planning and preparation as I navigated tricky sections of the trail and managed my energy over long stretches of challenging terrain.

The experience wasn’t without its difficulties. There were moments when the weight of the pack and the relentless elevation gain tested my physical limits. But those challenges only reinforced my determination and dependability—traits that are as essential on the trail as they are in my professional life as a Customer Success Manager. Just as I coach clients through complex projects, I coached myself through moments of doubt, relying on creativity and problem-solving to push forward.

• Day 1 – Timberline Lodge to Cloud Cap Campground
  14 miles

• Day 2 – Cloud Cap Campground to Ramona Falls
  19 miles

• Day 3 – Ramona Falls to Timberline Trail
  9 miles

There’s something transformative about solo backpacking. It’s an adventure that demands both physical endurance and mental resilience. But it also rewards you with a profound sense of accomplishment and discovery. Standing high up on Gnarl Ridge with Mt. Hood towering above, I felt a deep sense of balance—the perfect harmony of effort and reward, solitude and connection.

Completing the Timberline Trail solo was more than just a personal milestone. It was a journey that encapsulated my values of adventure, mindfulness, and persistence. It reminded me that success isn’t just about reaching the destination but also about the lessons learned and the growth experienced along the way. Here’s to finding success and discovery around every bend!

Where were we…?