Timberline Trail

With COVID still in full effect, we knew 2021 wouldn’t be a good year to try to reschedule our Haute Route trip that got cancelled last year, so for our family vacation we planned another road trip since we had so much fun on our trip to Colorado last year. But this year we planned the trip around including Tessa since we missed her so much last time. Destination: Oregon!

Our original itinerary had us driving up to Portland, then doing the Timberline Trail. Afterwards, we would drive to Bend and work remotely for a few days before beginning the Three Sisters Loop, then head home. But, what’s the saying? You plan, God laughs? Wildfires were everywhere, but were especially active in Northern California with the massive Dixie and Caldor Fires having a wide-reaching impact on air quality. And then Jon pulled his quad while playing softball, so we really had to adjust our plans to allow him to heal up a bit more.

Plan B had us starting with a weekend camping with friends, which was great! Then, on Sunday, we hit the road for Oregon. We found an inexpensive spot to camp near Weed, CA but the air quality was SO bad. Not a great place to be camping, but we were just going to sleep then hit the road again. I ended up feeling a bit sick for a few days afterwards, I think due to so much smoke exposure unfortunately.

On Monday we reached Oregon. Before we had adjusted our plans, we had booked a room at the historic Timberline Lodge. It was meant to be a reward for completing the Timberline Trail, but it ended up being a reward for driving to Oregon. We still thoroughly enjoyed our stay however, since we had been camping for the last three nights. The beds were SO comfortable. After so much driving, we just enjoyed the hotel, especially the outdoor space with the views of Mount Hood.

On Tuesday it was back to work. We drove over to Bend, where we worked remotely on Tuesday/Wednesday and explored the area a little bit. The smoke was worse in Bend so we didn’t really do anything too active but did get a chance to check out a brewery and meet up with friends who live in the area.

On Thursday it was time to hit the trail! But which trail? The Three Sisters area initiated a permitting process for the 2021 season, and I had been lucky enough to snag a permit for the weekend. Now we had to decide which trail we wanted to do: Three Sisters, or Timberline Trail? As you probably guessed, Timberline Trail won since it was cooler (literally; which is better for Tessa) and less smokey.

Originally we had planned to do the 40 mile loop in three days, but since we swapped it out for the longer Three Sisters Loop, that meant we could take a leisurely four days for the loop. We hit the trail heading counterclockwise in late morning and it was a perfect day for hiking!! When you leave the Timberline Lodge, the trail heads downhill through sand. In researching the trip, this was a topic of much debate: it is better to go up or down the sand. We felt that down the sand was WAY better, and the climb up to the Lodge that we had to do at the end was well worth the tradeoff.

We were also concerned about the water crossings, and by going counterclockwise, we would reach the most difficult crossings within the first day and a half, giving us time to abort and turn around if we felt unsafe. The other aspect that sealed the deal for us that counterclockwise is the best way to go is that a few miles into the hike, you actually go through a ski resort, complete with cell service and road crossings. We felt that it was best to do this section at the beginning of the trip while you’re still easing into the wilderness, versus creating the illusion of leaving the wilderness prematurely at the end of the trip.

And even though you were hiking under ski lifts, etc. this was actually quite a lovely section of the hike, with wildflowers and pretty stream crossings.

We would get our first taste of the water crossings right away. After a couple minor crossings, we reached the Newton Creek crossing in early afternoon. Crossing the boulders to reach the creek was challenging, but once there we were able to find a log crossing. One down!

We now had to decide if we would stop for the day or hike on – there was a dry section ahead of us, so we would have to push through if we kept going. I was tired but it was still early in the day, so Jon encouraged us to try to get in a few more miles. We hiked on, climbing up steeply away from the creek, and eventually making our way to Gnarl Ridge, which is supposed to have fantastic views but was unfortunately completely socked in with smoke.

I was getting really tired (and crabby) at this point, and was SO ready to be done. But we had no water, and would minimally need to hike to water before calling it a day. We found a small stream where we filtered a bunch of water and continued on.

The trail wrapped around Mount Hood, and we were able to escape the smoke finally. There was rain in the forecast for tomorrow, so we were now targeting staying at the Tilly Jane Hut, where at least we could stay dry while getting ready for the day. Neither of us had ever stayed in a hut before! This hut was pretty rustic with just a dirt floor, and it slanted, but it was much warmer and dryer than a tent.

Thankfully, the challenging day rewarded us with an incredible sunset over Mount Hood. It was just phenomenal.

As forecasted, the rain came overnight but we were warm and dry inside the hut. Since we had hiked 13 miles yesterday, today was going to be a short day, so we slept in and took our time getting ready to start our day – none of us were in a rush to go hike through the rain, including Tessa! Before we left some day hikers arrived, so we were able to get a family photo, then there was nothing left to do but hike!

Raimer Family picture!

It was a short hike (under 2 miles) to the Cloud Cap trailhead, which was also a campground, so we refilled water before hiking on. Today we had two major water crossings: Elliot and Coe. The trip reports from the last few weeks had looked promising for safe crossings, but we were less optimistic now that it had been raining for hours. We collected intel from hikers we passed on our way to Elliot, and learned that if you crossed at the rope and pull it downstream, it would help you avoid the deepest parts of the river.

I’ve never crossed water this deep and fast moving before. It was disconcerting to say the least. At the deepest part, the water reached my upper thighs! Jon was the real MVP – he crossed once to drop his pack, came back to get Tessa, then crossed a third time carrying her. Then I crossed last. The water was very cold as well, but thankfully the cold hit you more afterwards vs. while you are crossing. Then we had to climb up the insanely steep embankment on the other side. I don’t have any pictures of it because it was literal rock climbing through sand and I was guiding Tessa up as well. She listened so good, I was so impressed with how she knew when I wanted her to wait vs. go a different direction, etc. There must be an easier way down that we just couldn’t see from where we crossed!

After each crossing, you have to hike back up and out of the valley carved by the rivers. Before Elliot, we hiked through beautiful mossy trees and afterwards went through a section that was damaged by either fire or avalanche.

In the afternoon we reached the Coe crossing. Many people said this one wasn’t bad, and that you could do a three foot jump across boulders. However, due to the rain the boulders were all wet and slippery, and Jon and I didn’t feel comfortable jumping so we went across the river again. The rope at Coe was placed in a spot that looked like a terrible place to cross, so we crossed a bit lower. The water was really fast here, but thankfully not as deep as Elliot. Jon carried Tessa across again – our hero in this fast water!

Our destination tonight was Elk Cove, just a 7 mile day, but with the rain and stress of the crossings it felt like a much longer day, so we enjoyed a leisurely evening at camp. Towards the end of our hiking day the rain had finally stopped, although it was still pretty cold so some of that “hanging out at camp” meant “taking a nap in the tent”.

The sun was shining when we awoke on day three, and we were back to perfect hiking weather. The morning started with a climb that eventually took us to a section of trail with expansive views of all the area volcanos! We could see Mount St. Helens, Mount Rainier and Mount Adams – just incredible!

Mount St. Helens, Mount Adams, Mount Rainier

It was Saturday, so we also saw a ton of day hikers and trail runners. And I can see the appeal – the McNeil Point Trail section of trail was simply spectacular. The views of Mount Hood were so picturesque. But we all had to work for those views – reason #3 we like going counterclockwise: you do downhill through the blowdown!

Thankfully after the blowdown, it was more downhill but this time easy, fast downhill. We crushed miles and made quick time through the afternoon. The crossing at Muddy Fork was a non-issue thanks to a large tree we could skootch across.

We finally reached Ramona Falls, which were as pretty as the pictures I saw online! We took a little break to enjoy the falls, but quickly moved on after getting frustrated watching people climb up them just beyond the “do not enter” and “revegetation” signs. From here we had just about another mile to finish our day, claiming an awesome private campsite that could have easily accommodated several tents but we had it all to ourselves!

We got up early for our final day on the trial – we’d have a lot of uphill today – in fact, it would be the most elevation gain in one day of our whole trip. But thankfully it wouldn’t be through sand. HA!

“A lot of uphill” was no joke – it felt like it was ALL uphill, with minimal breaks. The highlight was hiking through Paradise Park – if you don’t have time for a long backpacking trip, or are looking for a beginner route, I would highly recommend this as an overnight destination. It offers incredible Mount Hood views.

No matter which way you go, there will be some climbing that final day. And, personally, I’d rather not do that through sand! Although today was pretty tough. Before we knew it, we were approaching the Lodge – we could tell by the number of day hikers passing us.

We loved the different topography that Oregon had to offer and can’t wait to come back and explore more beautiful Oregon trails. Hopefully we’ll be back to do Three Sisters soon!

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