Skagway is the taking-off point for the Chilkoot trail, so it was our first destination in our trip. I found Skagway to be a quaint, bustling little town tucked into the mountains. It is the northernmost port of the Inside Passage (the channels that run from Seattle to Alaska), and it gets huge cruise ships in daily. At first I couldn't for the life of me figure out why there were so many jewelry stores and fur shops in this town (my estimate: 3 out of 4 stores were for jewelry) until I realized that the cruise ships bring in fresh loads of hundreds or thousands of well-off people every day all summer long. I could just imagine what this town looks like in the winter: boarded up and deserted.
To get to Skagway by road, one must go through the Yukon Territory, a small section of British Columbia, the White Pass, as well as U.S. Customs just outside Skagway. A narrow gauge train runs from Skagway to Whitehorse in Canada, for tourists who want a beautiful train ride and a flavor of interior life. From Homer it was about 1100 miles; realize that we were just travelling to another part of the state of Alaska! It hit me for the first time how remote Southeastern Alaska is: most of the cities can only be reached by water. Skagway is one of the few that can actually be driven to, which makes it a popular taking-off and landing point for travellers (along with Haines, across the inlet a few miles away, but over 300 miles away by road).
Skagway is one of the oldest towns in Alaska (I'm guessing the tourist literature I read that in meant "non-native" oldest towns). It played a significant role in the gold rush of 1898 as prospectors would take the Inside Passage, load up their ton of goods for the 33 mile trek over the Chilkoot Pass, then take a boat (or in later years, train) to down the lakes to the Yukon River, which they would then follow all the way to Dawson City. Of the entire trek the gold rush hopefuls took to Alaska, only 33 miles was by foot; the rest was by water or train. It was that 33 miles which we were about to hike.
We liked Skagway. The RV park on Broadway let us pitch 4 tents on a patch of grass and use their showers for only $20 a night for all 9 of us. The food at the restaurant we went to was awesome (Skagway Brewery? Sorry, I forget). The lady at the laundrymat I went to was very nice, and I didn't feel like, "Just another one of those tourists," even though I came in with a fully loaded backpack of dirty clothes! It is a town we want to go back and visit again.