Circumnavigating Mount Hood

Danielle Chmelewski

One of my goals for 2020 was to dive into the world of mountaineering, but then COVID-19 hit and the world halted. I had plans to summit Mount Hood in Oregon and instead, I found happiness and adventure in my local Pennsylvania trail system. By the end of summer I needed something bigger, but it was hard to navigate what was safe and what was not. Flights were deeply discounted, but still at risk of being cancelled.

I took a risk and booked a flight to Portland, Oregon in August, planning to stay for five weeks to work remotely and spend every weekend finding new outdoor adventures. Staying this long in my own Airbnb in the green & spacious southeastern neighborhood, enabled me to feel safer and give me the space I needed to explore.

I thought, “Well, if I couldn’t summit – I want to at least do something epic around Mount Hood.” In steps the Timberline Trail. According to the All Trails app – a 41.4 mile loop with 10,341 feet of elevation gain and a stunning variety of landscapes and views. I met up with a couple of my friends in Portland and we picked a date and planned for three days, two nights.

We left the city around 7am on Friday, August 28. Everyone must have had the same idea – the parking lot at Timberline Lodge was already pretty full when we got there. We passed at least 10 cars of people, trunks open, gearing up and finalizing their packs. Some young skiers were even gearing up, which surprised me for the middle of the summer. One of the lifts was still running, supplying a tiny patch of snow for athletes to still train in the off season.

One final lodge bathroom break, an obligatory “before” picture, and we were off.

One river crossing, two river crossings, three river crossings while coinciding with the famous Pacific Crest Trail. An easy 10 miles mostly downhill in the morning brought us to Ramona Falls, a popular 120 foot cascading waterfall on the upper Sandy River west of Mount Hood. It was the perfect place to stop and rest for lunch.

Since it was a shorter trip and we weren’t too worried about pack weight, my trail mates did not mess around with food and went full out fancy. We were armed with fancy sausages, crackers, mini babybell cheese wheels, 8 avocados, a jar of Nutella, peanut butter, and chocolate. Best decision, hands down.

Exhausted after our day’s 17 miles, we had to head a bit off trail to find a camping spot. Thankfully we snagged a gorgeous opening where we could set up a tent and two hammocks. As we cooked our dinner, Mount Hood put on a sunset show for us. Growing more and more stunning as its peak quickly melted from golden orange, to pink and purple. The moon rose to the right of mountain through the pines but stayed low, so it didn’t drown out the stars above us. After a night full of storytelling and laughs, I crawled into my hammock, thankful for its coziness in the chilly 40 degree air, looked up at the stars and went to sleep tired and happy.

Within our first mile the next morning, we looked out across a vista that revealed stunning views of Mount St. Helens, Mount Rainier, Mount Adams, and the Three Sisters in the distance. My stoke was super high this morning. After a night under the stars, with good friends, lots of laughs, and warm oatmeal with freeze dried fruit, my energy was renewed and I was feeling on top of the world.

I started losing track of the number of river crossings. None were too intense, but did involve some careful calculations about whether you could jump or just take off your shoes.

We meandered through an incredible section of the trail just after McNeill Point that overlooked the remnants of the Dollar Burn fire, which ravaged north side of the mountain in 2011. With pearly white tree trunks still standing with no limbs, the forest floor offered bright green grasses and purple Fireweed flowers in stark contrast, showing evidence of the power of self-restoration. Walking across the ridgeline, we had views of Mount Hood to our right and the vast Cascades bobbing in and out of clouds on our left.

Another 17 miles on the second day had my knees screaming on the sandy downhills.

Our second night we tucked ourselves into a tall tree canopy next to Newton Creek. The wind that night woke me up. I felt my hammock sway and looked up to see the canopy shadows moving ominously like swaying giants. A little unnerved, I reminded myself that I looked for dead trees around me before setting up. I watched, nervous but mesmerized until I could no longer keep my eyes open.


Our final day, I struggled to get out of my hammock. My body felt wrecked. But I taped up my toes, popped a few Advil, ate my oatmeal and tried to bring some movement back into my joints for the last eight miles.

The last two miles was an exposed uphill in the middle of the days heat. I got a second wind from seeing Mount Hood at a different angle almost every mile. Every viewpoint was stunning. I settled into my uphill rhythm, not breaking stride – using my poles to counterbalance my steps. There’s something extremely satisfying about powering through a long uphill, finding your rhythm in your breath and stride. I will take it any day over a short, steep downhill!

Our final stretch to the Timberline Lodge parking lot had me smiling from ear to ear. We walked past a father and his little boy playing with remote control cars. We watched as one got stuck and the other pushed him out of a ditch – we all cheered together. 

There was a lot to cheer about that day. We finished a difficult 40+ mile trail, circumnavigating the mountains I had dreamed of summiting this year. And although I didn’t summit, I’m even happier that I got to see Mount Hood from every angle before doing so. And boy, she doesn’t have a bad side.