I went on a somewhat spontaneous two-day trip to Skagway, Alaska, in August 2019. Several people in town told me that hiking to Upper Dewey Lake (UDL), though quite strenuous, was worthwhile. Some said it was the best trail in the community. So, I decided to go on the hike the next day.
The trail is part of the Dewey Lakes trail system. While relatively simple to complete, it was physically demanding, seeing as I hadn’t hiked anything as formidable for a year or two.
A lot of the trail was an unforgiving ascent, reminding me of the Grouse Grind and part of the Gros Morne Mountain (James Callaghan) Trail hike. I was proud that I was able to do it, and the vistas were indeed rewarding.
The video embedded below offers a fairly comprehensive look at the journey. I put relevant video times in parentheses in this post.
I drove to Skagway from Whitehorse, Yukon, where I currently live, on Aug. 17. By the time I was ready to sightsee, it was 1 p.m. I asked a woman who worked at the hotel I stayed at if it was a good idea to go hike it right away. She warned against it, noting it’s a long hike and the windy conditions that day wouldn’t make it as enjoyable.
The hike begins
After a big breakfast, I began the hike at 10:19 a.m. the next day. I was back at the entrance at 6 p.m. I took many photos and videos, and I also made sure to spend time at the top to take in the views and think about the experience. I could have probably reduced the journey by three hours, if I wanted to rush it.
I stayed at Westmark Inn Skagway. My stay included free parking at a nearby lot that was close to the entrance of the trail system. A short walk past the train tracks (:32) got me to the entrance. There, there was a spot to brush shoes to prevent transporting the seeds of invasive plants (:40).
According to a sign on a nearby board (:44), a black bear was spotted on the trail system in May. A lot of people recommend carrying bear spray on hikes in the region. I saw at least one person carrying bear spray during the hike. I saw no bears but did come across what appeared to be, at least to my untrained eyes, a few spruce grouse (9:10).
Early on, I had to cross under a couple of pipes (1:05) that stretched up to the area of the first lake. I shared the trail with lots of caterpillars (1:40). There were some partly obstructed views of downtown Skagway (2:04) before I came across an outhouse (4:02).
Arrival at Lower Dewey Lake
The journey to Lower Dewey Lake had some of the steepest parts (2:48) of the entire trail to UDL. Most of the people I came across only went as far as that first lake, which is near Lower Dewey Reservoir. “Lower Lake Loop” (6:23) goes around the entire lake. I put that off for a potential hike when I came back (I was too tired, ultimately).
Later, there was a spot to either continue off to another toilet, Icy Lake, and Reid Falls, or head to UDL and the “Devil’s Punchbowl” (7:01). I went with the UDL option, of course.
Up it went… and up, and up, and up.
My calves remember that day well.
There were a few bridges, some stairs, and giant rocks (if that’s the correct term) that appeared to have had steps carved into them (12:32). The trail was well defined, and I never got lost. There were some trail markers (14:35) spread throughout.
There were a lot of “OK, I’m pretty sure the lake is just over this next hill” moments. Turns out, it was only safe to pre-celebrate once I reached the bridge at 19:21 in the video; I was quite close to UDL at that point.
Arrival at Upper Dewey Lake
Next to the lake (20:23) were a couple of cabins and at least one picnic table (20:15). According to the Skagway Recreation Center’s website, one cabin can be rented (21:24), and the other is first come, first serve (20:08). A wooden plank connected to a few big rocks (21:42) in the lake. I spent some time seated there to take in the views. It was a bit colder at the top but not uncomfortably so.
There weren’t many people there; it felt a little private. A short walk southwest offered up some of the best views (22:24). The trees obstructed most of the views on the trail until this point.
Further along that direction was the Devil’s Punchbowl. I was tempted to check it out, but I was too tired and too busy with other things I had to do that weekend. Pictures I came across online of the views from that spot suggest it would have been worth visiting.
I took no food with me to avoid attracting bears and to reduce weight of my bag. I felt a little hungry on the way back down. The hike wasn’t complicated, but it was physically tiring. The descent was tricky at times, namely given how steep some parts were, and also tired me out quite a bit.
I only went on two hikes during my trip to Skagway. Yakutania Point is a much easier and time-friendlier alternative.