Hiking the Historic Chilkoot Trail

Bekah and I have been staying pretty busy this summer with our jobs, guiding bike tours in Skagway, AK. While we have been getting out frequently for day hikes and long bike rides, our work schedule hasn’t allowed us much time for many overnight adventures. The first week of September, however, I was able to manipulate the schedule enough to allow a few days off in a row to hike the Chilkoot Trail with a coworker. Unfortunately, Bekah had to stay in Skagway and work. Since this was a rare trip that we did not take together this will also be my first time writing for the blog!

The Chilkoot Trail is a 33 mile footpath that runs from Dyea, 9 miles outside of Skagway, over the coastal mountain range to Lake Bennett in the Yukon Territory. For thousands of years, the trail was used as a trading route to the interior by the Tlingit tribes that are native to the coast of Southeast Alaska. As it was one of the only ways to access the interior during the Klondike Gold Rush of 1897-1898, tens of thousands of stampeders marched down the Chilkoot Trail during those two years with their sights set on staking claims in the Yukon. Today the Chilkoot Trail is maintained by the National Park Service as a part of Klondike Goldrush National Historical Park and is used recreationally by thousands every year. The Chilkoot Trail is sometimes referred to as “the world’s longest outdoor museum” because it is littered with artifacts left behind from the gold rush. When Caleb, a coworker at Sockeye Cycle, asked if I would hike the trail with him I enthusiastically agreed. After spending the summer speaking to guests about the history of the trail I was interested to see what it was like to hike it for myself. 

Our plan was to hike the 33 mile trail to Lake Bennett and ride back to Skagway on the White Pass and Yukon Route Railroad. We were able to get train tickets from Bennett to Skagway for Thursday at 2:45 pm. In order to hike the trail, we had to get permits and at 46 dollars per person I consider it a pretty expensive backpacking trip. It was also required by the National Park Service that we watch a bear safety video and attend an orientation before we were issued permits. We only had Wednesday and Thursday off so our plan was to hit the trail Tuesday after work and cover as many miles as we could so that we could take the other days easy and still make it to Bennett in time to catch our train Thursday afternoon.


I already had my bag packed for when I got off work Tuesday, and we were able to catch a ride to the trailhead, about 20 minutes from Skagway, and start hiking around 5pm. Caleb and I were pretty excited to get going and set off in a light drizzle at a pretty quick pace. The first portion of the trail is pretty flat, easy walking along the Taiya River. It wasn’t long before we reached Finnegan’s Point, the first of nine designated sites that you are required to camp at along trail. Although it was foggy and lightly raining, we still got a view of the Irene Glacier across the river. Finnegan’s Point is only 5 miles into the trail. We were anticipating getting much further the first night so after a brief stop we kept walking. More relatively easy hiking down the trail brought us to the next campsite, Canyon City at mile marker 7.7. We considered spending the night, but it was only a little after 7pm so we decided to hike three more miles to Pleasant Camp in order to shorten the distance we would need to hike the following day which included the big climb over Chilkoot Pass. We arrived at Pleasant Camp with enough daylight to pitch our tents, but we made our dinners in the light of our headlamps before heading to bed.


We woke on Wednesday to a very foggy morning. I wasn’t in a particular hurry to get hiking as I wanted to leave as much time as possible for it to clear up before we started climbing up the pass. The views are supposed to be amazing as you gain elevation but all I was anticipating was a thick wall of fog. Eventually we started slowly hiking. Although it was damp and foggy, the morning walk through the rainforest was quiet and peaceful. We started to gain elevation and the trail became more rocky with fewer and fewer trees surrounding us. Every once in awhile, the clouds would break enough for us to look back towards Dyea and get a glimpse of the steep valley walls and treeline below us.




 As the route became less of a trail and more of a scramble from boulder to boulder, I knew we were getting close to “the golden staircase” where the trail gains 1,000 feet of elevation in only a half mile. As we carefully made our way over the rocks, remnants of the gold rush began to emerge from the fog. We saw all sorts of items abandoned by stampeders as the trail got steeper from wood burning stoves and saw blades to tin cans or what I call historical litter. Eventually, we were using our hands and feet to scramble up a nearly vertical wall of loose rocks and boulders. This, we were certain, must be the golden staircase although the dense fog reduced our visibility to the surrounding thirty feet.




We continued up the steep path for nearly an hour before reaching the top of the pass and the U.S. Canadian border just after noon. There is a warming hut at the top of the pass, but we decided to continue over and down into the Canadian portion of trail before stopping for lunch in hope of better views. We began to descend through a narrow canyon. In less than an hour, we were back below the clouds in Canada. The views opened up and revealed the stunning valley before us. Emerald alpine lakes dotted the foreground with bronze slopes and jagged peaks taking up the background all framed by hanging glaciers on either side of us. The sun began to make appearances through the clouds and warmed us as we strolled without urgency.



Happy Camp is the first designated site on the Canadian side of the trail. When we were about 2 miles out we encountered a Canadian Ranger heading up the pass hiking with bear spray in hand. He told us he had seen a grizzly just above Happy Camp and that it may still be there. Upon hearing that we may have a chance at a bear sighting, we hurried cautiously along the trail. We scanned our surroundings as we approached Happy Camp but were not rewarded with any sightings aside from several large piles of scat.


We continued down the trail still keenly aware of our surroundings knowing that we were in grizzly country. Our destination for the day was Deep Lake at mile marker 23. We arrived around 4pm and were the only ones at the campground. We took our time to explore the camping area and pick out prime sites for our tents. The campground is located on the side of a hill overlooking Deep Lake, and there are wooden platforms to pitch your tents on. It was a beautiful spot to spend the night. After dinner a steady breeze chilled the air so I retired to my tent to get cozy in my sleeping bag. Thursday brought us the best weather of the hike. We only had ten miles to hike before catching the train at Bennett so we casually hiked the mostly downhill trail enjoying the abundant sunshine. We took breaks at the remaining two campsites, Lindeman Lake and Bare Loon Lake.

Around 1:00 PM we crested over a small hill to reveal our first views of Lake Bennett, a stunning glacially fed alpine lake that eventually pours into the Yukon River. Once on the shore of Lake Bennett, we had made it to where the stampeders of the Klondike gold rush would have built boats and floated the remaining 500 miles to Dawson City. We checked out the small museum and laid around in the sun for about an hour before hearing the ever so familiar whistle of the train as it rounded Lake Bennett. We boarded the train and two hours later we were rolling to our stop back home in Skagway.




We are Sean and Bekah, enjoying one bit of Infinite Geography at a time. We just wrapped up our season guiding bike tours in Alaska and are hitting the road on our first bike tour down the west coast. Follow our journey here, on Instagram, or on Facebook.

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