Chat with Deb—Oh Little Town of Skagway

“What’s that big white building at the end of the street? Oh, wait, that’s our ship…”

Jack Herlocker
5 min readJun 29, 2022


Previously, on Deb & Jack’s Alaska Adventure:

DEB: So I guess the day after walking—

ME: Stomping!

DEB: — on top of a glacier, today will be much more relaxing. A relaxing train ride in the country!

We had woken up in Skagway, a quiet little town. Surrounded by lovely mountains, because why the hell not?

The view out our windows at breakfast. (all photos by author unless otherwise noted)

With a train track leading up to the pier. Okay, wasn’t expecting that.

Ah! If this had been an industrial port, back in the day (which it was) then OF COURSE the tracks run up to the piers! And still do, only now the cargo is people. Also: note the lovely trees with new leaves popping robustly, while the mountains a short distance away are still snow covered. Native reaction: “Oh yeah, that happens here.”

We join our excursion group and board our appointed car; each car has its own guide.

GUIDE: Welcome to Skagway! And welcome aboard the White Pass and Yukon Route railroad. We will be traveling to the White Pass Summit, about 20 miles away and 2,888 feet in elevation, and then returning to Skagway. The rail line goes into Canada, ending in the Yukon Territory in Canada, but we will be staying on this side of the border today. I will be calling attention to items of interest as we go along, so please relax and enjoy the trip!

A view out the train as we go around a bend. Notice the trees have fewer green leaves and the mountains have more snow. Also, the peaks in the middle of the photo have wispy clouds on them; I asked one of the guides, who said that was not unusual, as many of the taller mountains generated their own weather phenomenon. I noticed this happening frequently in Alaska once I started looking.

The WP&YR railroad was started in 1898 after gold was discovered in the Yukon. Prospectors and assorted folks were struggling over the mountains and through the passes, often on trails barely wide enough for pack animals, with heavy losses of both people and animals. The narrow-gauge railway was completed in 1900, just in time for the gold rush to go bust. Other mining efforts provided ore that needed transport to the ocean, so the railroad was able to get along until 1982, when commodity prices for metals plummeted and the WP&YR had no business purpose… until a few years later, when it reinvented itself as a tourist train.

A part of the WP&YR no longer in use, for obvious reasons. We’re about 2,600 feet up, and the few trees that remain have NO leaves to speak of.

DEB: Oh my! Some of these views are gorgeous!

About 2,800 feet in altitude, near the top of the pass. No more trees— no, wait, there’s one! (I think it’s a tree. )

GUIDE: For those of you who are thinking, “Gee, there’s a lot of snow, it must be an Alaska thing!” We had a hundred-year snowfall over the winter. Even for us, this is a LOT of snow!

I couldn’t get a good “blue hue” effect from the snow on the glacier the day before, but the compacted snow in the mountain passes was almost as good!

The trip back was basically the trip up, looking the other direction. Still pretty, but no new photo ops. The train stopped where it had started, at the end of the pier where Nieuw Amsterdam was tied up. Door to door service!

DEB: I’m thinking we have lunch on the ship¹, then wander into town and check it out. Sound good, Jackster?

Looking down the main street of Skagway, during Thursday rush hour.

Skagway turned out to be a delightful little town, with the main street mostly tourist-oriented shops. We stopped in many of them, but we did not buy much because we are downsizing (Real Soon Now) and we do NOT need More Stuff.

Unless it’s really cool stuff.

DEB: Oh honey, look at this! Isn’t it wonderful?

Christmas creche, Alaska style. My wife goes ga-ga over nativity scenes, and I enjoy indulging my wife, who never asks for very much. (No, seriously, she doesn’t! Most of the time when Deb asks for something, it’s for somebody else, not her.)

ME: Okay, we’re buying it!

And it did not cost much, anyway. The advantages of being at the front of the tourist season.

The reverse look down Skagway’s main street. The big building at the very end of the street? That’s our ship.

Back on the ship, we stopped at the Future Cruise Desk. Holland America Lines offers a discount if a passenger books their next cruise while still on their current one — because what sells the next adventure better than the current one, eh? Plus, we were interested in a US/Canada cruise through New England, the Maritimes, and Quebec City, which HAL offers.

But not in 2023, it turned out.

DEB: Well… shoot. Too soon to look at 2024, in any case.

ME: (to booking agent) So, do you have anything that runs through Quebec City?

AGENT: Hmmm… I’m afraid not. Although we do have this one. It starts in Boston, stops in Nova Scotia, Newfoundland, Labrador, Greenland, and Iceland, then returns to Boston. About three weeks. (shows us the map)

image from HAL’s website

DEB: Oh wow! We’ve talked about Iceland, Jackster! How much? (agent shows us the price options) Oh…

ME: Let’s do it.

DEB: Honey, we’re moving into a retirement home in a few years. What if we need the money?

ME: What if we move into the home and we have money left over, but our health is shot? Probably we’ll still be in good shape next year. Let’s do it.

AGENT: You can cancel any time up to the final payment next April. With full refund.

ME: Let’s do it.

DEB: Well… okay, if we can cancel if we need to…

We’re going to Iceland, people!²

Dinner was at one of the premium restaurants — specializing in seafood, in this case. We had escargot, Dover sole (filleted right at our table by our waiter), halibut, and dessert soufflé. Dang!

These were just the decorative plates—we thought they were kinda cool.
Halibut and dessert soufflé. Yes, we packed Tums for this trip. Not that there wasn’t plenty in the ship’s store, for some reason.

Then back to our cabin.

DEB: Come see the moon, honey!

ME: (holding my wife next to me as we got underway from Skagway, standing together on our verandah and looking over the mountains) Pretty cool, pretty lady!

Already twilight down at sea level (and quite a ways above), but the sky is still blue and the mountains have that sunset tint to them.

Deb gives me an extra squeeze and a kiss. I give her an interrogative look.

DEB: (loud whisper) We’re going to Iceland!

¹When all meals are included in a cruise package, it does not matter how lovely the restaurants on shore look, you eat on the ship.

²Yes, I know, we said that about Alaska in 2020. And 2021. Shush!



Jack Herlocker

Husband & retiree. Developer, tech writer, & IT geek. I fill what’s empty, empty what’s full, and scratch where it itches. Occasionally do weird & goofy things.