ChatGPT’s first cut at a day off the cruise ship in Skagway, Alaska (6:30 am-7 pm):
This is probably your most natural hiking day. Do Lower Dewey Lake in the morning; it’s a real forest/lake hike close to town and cruise piers, and multiple Alaska cruise hiking guides recommend it as one of the best port hikes in Skagway.
Then do the Klondike Gold Rush National Historical Park museum/historic district. The NPS says its Skagway historic-district walking tour is a 0.64-mile self-guided tour, and the visitor center/museum and restored Mascot Saloon are part of the park experience. This gives the boys context for the gold rush without sacrificing the active day.
Again, ChatGPT shied away from “overtouristing” by giving us a lightweight schedule. Pressed, it also recommended riding the White Pass railroad, which, as it happens, was a pioneer in containerization.
We ended up not doing the Lower Dewey Lake hike because the only time available for the railroad was mid-day, it took us a while to get organized in the morning, and the train ride took longer than expected due to a locomotive failure.
Walking towards downtown from the cruise pier:
Crossing the railroad tracks:
I remembered the town as sleepy when I visited in 1993. Here’s a photo from the absolute peak of the tourist season in 1993, July 25:
For comparison, May 2026 (well before peak tourism; looks like the weather improved, at least, thanks to Climate Change!):
Quite a few of the sidewalks were covered to Times Square densities:
Because it was Memorial Day, we used Google Maps to navigate to the “young men who left home and community to answer the call to help preserve peace and freedom in the world” plaque:
These men fought and died so that we could have Rainbow-first Retail and so that people could preferentially shop at stores that proclaim “women-owned” (because “Women have always been the primary victims of war.” (Hillary Clinton)):
If they hadn’t been killed in wars they could have come home to drink at a brewery under the sacred flag:
The National Park Service explains the alternatives facing the “Sourdoughs” prior to the railroad’s construction:
The gold rusher had to bring a minimum of one ton of supplies up these trails in order to get through Canadian immigration. Unlike today, where being helpless and in need of four generations of welfare enhances one’s admissibility as an immigrant to Canada or the U.S. (as a “refugee” or “asylum-seeker”), the Canadians at the time didn’t want anyone who was likely to become a dependent. Therefore, they inspect a miner’s luggage to make sure that he had at least one year of food.
The railroad promised to change all that, but it wasn’t finished until the gold rush was over (Wikipedia), but the investors still made money because there were other resources, including copper, silver, and lead, to be pulled out of the Yukon. Uncle Sam stepped in to save the railroad from the Depression by taking over the system during the construction of the Alaska Highway in WWII.
Passengers in the uncrowded Alaskan wilderness ready to get on…
The trip starts fairly flat.
At a few points it is possible to see Skagway and any cruise ships docked there:
We sat next to a Mexican real estate developer. He and his wife were big Trump supporters because they believe that Trump will help quash the cartels that compromise safety within Mexico. They do not like their progressive president, Claudia Sheinbaum, due to inefficiency, cronyism, and failure to deal with organized crime. Although not Jewish, they dislike Sheinbaum’s support for Hamas and frequent condemndation’s of Israel for “genocide” (exacerbated in Gaza by rapid population growth). “Even if she were right about Israel,” the Mexicans pointed out, “what does the Gaza war, or any war in the Middle East, have to do with Mexico and Mexico’s problems?”
Here’s a reconstructed border shack where the Canadian government used to try to make sure that immigrants could be self-sufficient:
After one of our locomotives failed, a train in front of us sent back one of its two to help us up the final steep ascent. Then we used our own single locomotive for the trip back down to Skagway. Have faith in timber:
The term “Gold Diggers” has a different meaning here than in the lower 48. From the downtown bookstore:
We decided that the kids weren’t ready for this:
A fun souvenir:
How did ChatGPT do? Fair. The railroad trip is more or less essential, in my opinion, despite the extra sitting time. It’s the only way to experience the reason that Skagway exists, i.e., getting through the pass. Furthermore, it has to be booked well in advance because the trains fill up. There isn’t enough to do in downtown Skagway, even with a hike, to fill up a whole day.