Diamonds. Twelve varieties of ‘ALASKA’ t-shirts. Crowds of people. And even more oddly, Santa. I had just arrived in the tiny town of Skagway, Alaska and I was confused already. Before arriving in Skagway that August day, all I knew of Skagway was that it was the starting point of the Chilkoot Trail, the route thousands of gold-seekers used to travel up and over the mountains in the late 1890’s on their journey to reach Dawson City, the epicenter of the Klondike Gold Rush (1896-88).

I thought Skagway would be like Dawson City; a cute, historic ex-Gold Rush town with a whole lot of wilderness spirit. Plus mountains. Well, Skagway is a bit like Dawson. The town just happens to be a cruise ship port as well.

Skagway buildings mountain

Downtown Skagway Alaska gold rush town

White Pass Yukon Skagway Alaska train

a town of contrasts

On a high from crossing the US border for free (the payment machine was out-of-order), I was welcomed into Skagway by the sight of three gigantic cruise ships. I could spot mountains and a glacier or two behind these huge white monoliths. It was a strange contrast.

Thinking I’d take a little wander before heading to find a campsite for the night, I walked down Skagway’s main street in shock. Every single one of the restored shops seemed to be selling every kind of Alaska branded made-in-China merchandise imaginable plus half a dozen diamond sellers and a Christmas store. And then I started to notice anyone around me. These were not people who were sleeping in their van, showering once a week and cooking on a campfire. I suddenly felt quite out-of-place and made a hasty retreat. Luckily, I did not have to go too far to find an escape.

Skagway inlet Alaska

taiya river bridge skagway dyea

Dyea disappearing town Skagway

From gold miners to cruise ship tourists

Dyea (pronounced die-ee) is a largely abandoned town a few kilometres away from Skagway. It was a boomtown in the Gold Rush days with the start of the 53km Chilkoot Trail located just behind it. Today, it is mostly National Historic Park land, accessed by a narrow road alongside the Taiya inlet. There’s also a nice enough campground with sites available for $10/night. I stayed here, along with a handful of hikers heading out on the Trail the next day.

I took a trip out to see the trailhead myself, half wishing I was leaving Skagway this way. Checking out what was left of Dyea (not much; it really is incredible how evidence of human existence can disappear so easily sometimes) I then headed back to town to buy a ferry ticket to get out of Dodge.

The gold miners heading out on the Chilkoot Trail arrived by ship, usually from San Francisco or Seattle. The majority of visitors to Skagway still arrive by water, though the actual form of transportation is certainly different these days.

The cruise ship thing honestly wouldn’t be such an issue if Skagway was bigger, but it really is just such a tiny town. The total population may double during summer but it still hovers around 2000. It is an exceptionally small place to have such big boats dropping thousands of people into town every day. But the local economy must do very well out of it. Dyea Skagway building

Gus Taylor headstone dyea cemetary

Chilkoot trailhead Dyea Skagway

Chilkoot double trail monument

An empty National Historic Site

I admit it, I did go in a souvenir shop – one that had an ATM with cheaper transaction costs than the Wells Fargo bank a few doors down. With American dollars in hand and a ferry ticket purchased, I went on a walking tour of the town after procuring a guide at the strangely quiet Visitor Information building. Choosing one of the sights away from the main street at random, I ended up at the Moore Homestead, a National Historic Site.

William Moore was a clever and industrious guy. A bit of an expeditionary, he concluded that gold was likely to be found in the Klondike area since it had also been discovered in similar mountain ranges elsewhere. Moore settled in what is now modern Skagway, believing that this area would provide the most direct route to the goldfields and would be a strategic place to set up business. He was right.

Moore’s homestead sits just a few steps (around eight to be precise) away from the main street and it felt like it was in a different world. The Ranger inside was happy to see me and offered a little tour of the exhibits inside the museum. He said that they didn’t really receive many visitors. 

Downtown Skagway Alaska

Historic Moore Homestead Skagway Alaska

White Pass train Skagway Alaska Yukon

Skagway ferry Alaska

a return to skagway?

On paper, Skagway sounds great. I wanted to like it, I still do. I want to hike the Chilkoot Trail and then take the White Pass train back (built 1900, just as Gold Rush fever was dying down) and follow it all up with drinks in the Red Onion Saloon and a walk to see one of the beautiful waterfalls near town. The scenery around town is incredible and I so wanted to enjoy it. But it was hard to get my head around all those cruise ships. Maybe I should just visit in winter. Regardless, I will be back, even though I didn’t enjoy it the first time.

If you’re wondering what Skagway looks like without the cruise ships, check Murray Lundberg’s excellent blog.

Skagway cruise ships Alaska

Have you ever been anywhere you hated but could see the appeal? Anywhere you didn’t initially like but would visit again? Let me know in the comments!


One half of a Canadian/British couple currently living in Penticton, British Columbia. Gemma is happiest with a paddle in her hand, on the trail or planning the next big adventure.


  1. Pingback: Our Western Canada road trip: Week 17 and 18 | Off Track Travel

  2. If you only saw half a dozen diamond sellers, you missed about 20! 🙂 You need to come back and see it off-season now – even late April and early May are great as the town wakes up from a quiet Winter.

  3. We took an UnCruise expedition last May and found ourselves in Sitka with a day to kill before our boat took off. We visited all the places off the beaten track and many people seemed quite surprised to see us. It was lovely. Your experience in Skagway sounds a lot like what we experienced in Ketchikan.

    • Gemma
      Gemma Reply

      That does sound very similar! Great to hear of others trying to see something other than diamond shops!! It was actually really nice to have a good chat with the Park Ranger about the area and the historic site, something I may have not been able to do if it was busier. So swings and roundabouts! I heard lots of people on the Haines ferry talking about how stopping in Sitka was a ‘must.’

  4. You obviously weren’t there in winter! These photos make it look quite wonderful. I’ve been curious about it ever since reading up on gold diggers in the Yukon – what a fascinating time in history. Glad I visited Dawson instead (though I’d still like to go).

    • Gemma
      Gemma Reply

      I love all of the gold mining history of the Yukon, it really is so interesting and I knew so little before I went! Dawson City is one of my favourite places in Canada, I’m glad you liked it too!

  5. Enjoying your posts, found them off Murray’s site. We travelled and camped Alaska by car for 15 years nearly every summer until my wife got tired of it all and luckily coincided with my brother’s (who lives in Alaska) buying a cabin down in Homer…hard to beat a bed for a 2″ camping mattress after a while (and the BUGS!). Miss the travels and little adventures.

    • Gemma
      Gemma Reply

      Hi! Thanks for your comment, I’m glad you’ve found us. 15 years of exploring Alaska?!! Wow, I’m very impressed. How convenient for you for your brother to buy a cabin in Homer once you were done 😉

      • Hi Gemma,

        It sure helped to have the brothers connection in Anchorage to give first and last night accomodations and places to store/share/borrow gear from summer to summer…

        And a GF then wife* who got hooked a bit on travelling to the north, but finally too many vacations crammed into a small rental car, sleeping on thin Thermarests, no chairs, no running water, no showers (and too many bugs!)…too much. And then big bro bought a nice oceanside cabin outside Homer with stunning view of snow covered volcanoes…plus eagles, whales, salmon, otters…and real beds. Not bad at all.

        Interestingly enough, Homer is “the end of the road’ in their advertising…


        *wife planned wedding, etc. Hubbie planned honeymoon – Alaska!

        • Gemma
          Gemma Reply

          Oh for sure! I like your honeymoon style 😉 Your brothers cabin sounds amazing! Would have loved to make it to Homer.

          • southcove

            I was going to include a picture I took from the landing at the cabin, looking up towards the volcanic mountain ranges outside Homer…kayaker (my older bro doign some get a way time…) in the distance, dramatic sunset at 10pm… but you have seen all that before in one place or the other – and you UNDERSTAND already!

  6. WoW… Doesn’t sound like you’d make it over the Chilkoot Trail to Dawson. If the pics you posted are from your day in Skagway, then lucky you to arrive on a quiet day. Skagway’s livelihood is tourism. We handle it just fine.

    There is tons of wilderness here. Sounds like you opted to hang out in town then kvetch about it. This is the Tongass National Forest …almost 17 MILLION acres. Google it. Pshhhht!!!

    • Gemma
      Gemma Reply

      Hi Louise,

      I think you must have misread my post? I pointed out many nice places in and around Skagway that I visited during my two days there, but also concluded that it not the place for me in the summer as I do not like crowds. Planning the Chilkoot trail for 2017 and looking forward to it already!

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