Skagway, Alaska

Skagway

Unless you have taken an Alaskan cruise, I’m going to guess Skagway is one of the most interesting places in the United States that you’ve never heard of. Skagway, AK, has a permanent population of about 800 people, which doubles in the summer with all the seasonal workers it requires to function. Skagway is not an easy place to get to. You can either take a ferry, which takes about an hour from Haines, and about six hours from Juneau. You can drive from Whitehorse, which takes about two hours, and is almost all uphill, until you get to the border. Or, you take an Alaskan cruise. Every single Alaskan cruise stops in Skagway, as has been the case as long as there have been Alaskan cruises, since the Klondike Gold Rush of 1898. Oh, I almost forgot, you can also take a  62-hour ferry from Bellingham, Washington.

During the Gold Rush, the easiest way to get to Dawson City was to sail to Skagway, carry 1 year’s worth of food plus your supplies up the Chilkoot Trail, which generally takes about four days per trip, and would require multiple trips for all of your goods. Once you reached the top, you could grab a Sternwheeler from the headwaters of the Yukon River, Lake Bennett, to Whitehorse, then take another Sternwheeler from Whitehorse to Dawson. Simple. Some crazy people still hike the Chilkoot Trail, but I am not one of those. It’s 33 miles, mostly up. You don’t have to take a year’s worth of food anymore, but you will definitely end up regretting anything unnecessary that you bring.

Skagway is home to the White Pass Railroad, which offers train rides either to the summit, around 3200’ up, or to Carcross, Yukon, where you are a short 20-30 minutes from Whitehorse. The track runs 67.5 miles and travels through the Coastal Mountain Range, to a plain that looks moonscape, at the base of mountains covered in trees that only look tiny compared to the mountains. Past countless glacier-fed lakes, some of which (Emerald Lake, Spirit Lake) look emerald green, you will arrive in Carcross, home to the world’s smallest desert (technically it’s semi-arid so can’t be called a desert)

You are experiencing something truly unique if you find yourself in Skagway with no cruise ships docked. Only one cruise ship is considered pretty lame, and on days with no cruise ships, many business don’t even bother opening. But, on the days they have 4-6 cruise ships, there can be more than ten thousand tourists at once. That’s 10 000 day-visitors in a city of 800. Woah.

The biggest hotel in Skagway is the Westmark Inn, conveniently owned by Holland America Cruises, who offer many Alaskan cruises. I always used to stay there because I worked for the Westmark for my first 3 years in Whitehorse, and it certainly has its charms. All the staff I have ever interacted with have been friendly and efficient. The hotel is generally full of cruise ship guests (most are 70+), and close very shortly after the last cruise of the season, which I believe is mid September (the first is mid May). The walls are very thin, so you can expect to hear first hand what sorts of health issues your 70+ neighbours have developed. Ours sounded like he was about to hack up what was left of his lungs. It is in a great location, with a terrific view of the train station and waterfront (full of cruise ships). 

There are a couple other accommodations downtown, such as At the White House and the Morning Wood Hotel and Happy Endings Saloon, but I prefer to stay at the Swaying Spruce Cabins or Skagway Bungalows. They share the same road, off the Dyea road, and are definitely the sorts of places I think of when I think Alaska. The Swaying Spruce has three log cabins in a rainforest, with an unobstructed view of the mountains and a waterfall. They also have the sweetest dog. Whatever form of accommodation you choose, you should expect to pay $200-$300 a night for a room

Skagway is packed to the brim with jewellery stores, souvenir stores and restaurants. One walk down broadway and you will likely find yourself bored of tanzanite and free cruise charms, with a full belly, an ‘Alaska the final frontier’ fanny pack, and either a triple scoop of ice cream from the Kone Kompany, or a bag of caramel corn from Yukon Heath’s Popcorn Emporium.  They have a special symbol for things that are actually made in Alaska, to set them apart from places like the Alaska T-shirt company, which is too cheap not to be made in China.

I don’t think I’ve ever had a meal in Skagway I would classify as bad. There have been one or two that were pretty good, and that’s about at the worst its been in 12 years. I am never disappointed by the Skagway Brewing Company. They have an excellent gluten free bun, the truffle fries are out of this world, and they have a ton of seafood I am sure is delicious, but I haven’t tried since I don’t really like eating seafood. 

The Red Onion Saloon has an amazing gluten free pizza, and an impressive-looking non gluten free pizza that’s 15” and has something like 12 slices. Their nachos are definitely big enough for two people. When we arrived, there was one server and five tables of 4-8 people. They all left within about ten minutes, and that was the only time we saw more than one empty table in a restaurant.

We used to eat at the Sweet Tooth Cafe for breakfast, but since our last visit in 2019, they closed, though we heard it was for non-pandemic related reasons. This time, we went to Bites on Broadway, that has a very impressive menu, and hands down the best gluten free bun I’ve ever had. We got the last free table when we went for lunch, and it filled as quickly as they could clear tables. The owner was always on hand, did a quality check of every table at least once, and was obviously focused on creating positive guest experiences.

We both had grilled cheese sandwiches at the Bonanza Bar & Grill (attached to the Westmark by a very weird maze of hallways), which came with a tomato reduction that was an excellent replacement for ketchup, and very yummy fries, It was packed the whole time we were there.

As a side note, if you are a server or bartender and you want to work your ass off and make a bucketload of money, think about getting a summer job in Skagway. If you can bring your A game every day and resist the urge to party away all your nights, you will end the season feeling like you struck gold. If the thought of working in a restaurant where your section may have ten tables and they may all be full for your entire shift intimidates you at all, it may not be the right choice for you.

Alaska is an amazing state in a lot of ways. It is amazingly big, and amazingly difficult to traverse. It has the most amazing scenery I have ever seen, the most amazing hikes I have ever taken, and leaves you with the soothing afterglow of spending more than $150 a day on food. Cannabis is legal in Alaska, and Skagway has a dispensary called the Remedy Shoppe. All the cannabis sold in Alaska also has to be grown in Alaska, so you are likely to have a much different experience than you may be used to.

Skagway is an amazing anomaly. Its origin, to provide a route to the Klondike Gold Fields, still took so long that by the time most of the prospectors reached Dawson City, the gold rush was over, but Skagway and the cruise ships, still remain.