A Love-Hate Relationship with Skagway, Alaska

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 famed Chilkoot Trail.

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. Read on for my experience in this beautiful yet baffling Alaskan town. 

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Wooden store fronts on Skagway's main street
The small town of Skagway, Alaska
View of downtown Skagway with mountains behind
Train at station with crowd waiting to board
The White Pass train, Skagway
Skagway cruise ships Alaska
Cruise ships and mountains in Skagway, Alaska

Skagway, Alaska: 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 and cooking on campfires. 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
Rusting bridge over green river, Skagway
Taiya River bridge to Dyea in Skagway
Dyea sign in front of patch of grass
The disappearing town of Dyea, 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.

The Chilkoot Trail was 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).

Today, Dyea is National Historic Park land, accessed by a narrow road alongside the Taiya inlet. There’s 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, wishing I was heading out on a Chilkoot Trail hike. Checking out what was left of Dyea (a wonderful walk in the woods with interpretive panels), 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.

Dyea Skagway building
Building remains, Dyea
A wooden headstone surrounded by ferns
Gus Taylor’s headstone in Dyea Cemetary
Chilkoot trailhead Dyea Skagway
The start of the Chilkoot Trail
Trail through forest, monument with two miners leaden with backpacks
Chilkoot trail (left) and monument in Skagway

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 guidebook 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. 

Historic Moore Homestead Skagway Alaska
White Pass train Skagway Alaska Yukon
Ferry terminal, backdropped by mountains and glacier
Skagway’s ferry terminal
Downtown Skagway Alaska

A return to Skagway, Alaska?

On paper, Skagway sounds great. I wanted to like it and I do in a way. 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 Skagway 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.

Things to do in Skagway, Alaska

For such a small town, Skagway does have a lot of activities and attractions to offer, undoubtedly at least partly due to the cruise ship visitors. Here are some ideas for things to do in Skagway, Alaska. Of all these suggestions, I’d highly recommend taking the short drive out to Dyea if you can! 

Looking to book a stay in Skagway, Alaska?

Historic Skagway Inn – Great value

Westmark Inn Skagway – Highly rated on Booking.com

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

With a mix of coastal Alaskan scenery, diamonds and cruise ships, Skagway is a beautiful yet baffling town. But there is still plenty of wilderness spirit if you know where to find it. Click here to discover more about this small Gold Rush town! offtracktravel.ca
With a mix of coastal Alaskan scenery, diamonds and cruise ships, Skagway is a beautiful yet baffling town. But there is still plenty of wilderness spirit in this small community, even if it is hard to see in the height of summer. Click to discover our experience in Skagway plus a quick things to do guide for your own visit! offtracktravel.ca

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15 thoughts on “A Love-Hate Relationship with Skagway, Alaska”

  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.

    • 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).

    • 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.

    • 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!

          • 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!!!

    • 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 2020 and looking forward to it already! It’ll be a great hike.

  7. Hello! I thought your article was really funny seeing as I have lived in Skagway my whole life! It definitely is a little odd; the mix of cruise ships and jewelry stores. Probably more than half the buildings in town are jewelry stores. One weird thing that happens around July is a cruise ship that comes in filled to the brim with Santa Clauses. It’s a strange sight to see: hundreds of Santa Clauses and Mrs. Clauses wearing hawaiian shirts wandering about all day.

    Adalia Deach
    8th grade
    Skagway, Alaska

    • I’m glad you found the post funny Adalia! It’s really great to hear from someone who has grown up in Skagway! A cruise ship filled with Santas sounds very entertaining!!


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