If you’ve come to Skagway in hopes of sleeping in, forget about it…unless of course you are deaf. At precisely 5 AM the train whistle sounds not once, but at least a half a dozen times! We roll over, pull our eye shades back over our sleep caked eyes and do our best to get back to sleep, as the permit office does not open till 8am. At 6am, one of the now 3 cruise ships docked in Skagway sounds its horn, alerting it’s passengers that ‘we’re at another port, time to get a move on if you’re gonna fit in all your sightseeing for the day’. Mind you, Skagway is relatively small, but chock full of history if you care to take the time to seek it out. Downtown is essentially a National Park. The Klondike Gold Rush National Historic Park, to be exact. Interpretive signs, and historic buildings with colorful stories abound. Numerous tours with a Ranger are available, as well as private tour companies, and a ride on the White Pass &Yukon Route railroad, a float plane or even a helicopter. Today we skip all the touristy stuff, and after a JetBoil-ed cup of coffee, and a smushed Hostess apple pie, we pack our packs for the Chilkoot, drop Schluffle off in the RV park’s shed and march off to the permit office. We wade through throngs of hiker clad “boat people” wandering the wooden slatted sidewalks, as storefronts do their best to entice them into their shops for trinkets and memorabilia that could just as easily have “Florida” stamped on it. Annoyed by the muddled masses moving like the walking dead along the sidewalks, wearing billboard t-shirt, hats or jackets passively announcing from whence they came (as ironically did we), we weave and step around them, like salmon swimming upstream to spawn.

(We…and several other hikers we came to know…would later call these two young men the “Peanut butter Boys” as they carried a LARGE jar of Skippy peanut butter to make PB&J sandwiches)

When we reach the permit office, we set our packs outside and get in line. It is obvious, we are not the only ones starting today. We present our reservation to the Ranger, and after a trail orientation, we are issued our permits.

We are told that one section of the trail (Deep Lake to Lindeman City) there is a “bear problem” and are encouraged to walk in groups of 4 or more. Do we need bear spray, we ask. “It’s recommended”, we are told. But do we REALLY need it? “It’s recommended”, was the reply again. So we don’t have to have it? “It’s recommended”, smiled the Ranger, who by now was annoyed, as were we, when we were asked the same question repeatedly. We elect to go without it, figuring if a bear gets close enough for us to deploy the spray, we’re gonners anyways.

The trail does not start in Skagway, but in Dyea, almost 10 miles away. Many have hired a “taxi” service of sorts (to the tune of $20/person) to shuttle them to the trailhead. We are cheap and able-bodied (mostly cheap) so we elect to walk there. The Ranger shows us a “short-cut” to the road to Dyea that will shave off “2miles”…go figure. This “short-cut” is perfect, as it’s on our way to pick up our train tickets for our return trip to Skagway from Bennett Lake. Of course had we known we had to pick up our tickets beforehand, we would have done so on our way to pick up our Chilkoot Trail permit. Thank goodness the Ranger at the permit office asked how we were returning, otherwise, with our luck, we would have had to walk back. Once we picked up our train and box lunch vouchers, we tucked them safely into the folds of our passports…to get back into the USA… legally. We considered taking the “longer route” as opposed to the “short-cut” recommended by the Ranger, seeing as “short-cuts” are not always “short-er” for us. However, as you probably already guessed, being the eternal optimists, the “short-cut” option prevailed.

Once we cross the Skagway River, the trail heads to the left and of course, uphill all the way to the dirt road that now winds 7-ish more miles to the Chilkoot trail head. We begin our walk toward Dyea, several vans loaded with people pass us and wave. We continue walking, it’s nearly 10am and at our pace we reckon we’ll get to the trailhead around 1pm. After about 45 minutes we hear another vehicle approaching from behind. I raise my sunglasses, smile brightly and put out my thumb. SUCCESS! A well used truck with a solo occupant pulls over. He says he can’t take us all the way, but at least he’ll save us a hill to climb. He is a transplant from Atlanta Georgia, and has fully embraced the Alaskan way of life. We reach his turn off, where he is building a house. We thank him for the ride. I forget to get his name, but with his permission, I get a photo of our first trail magic, and Trail Angel.

We begin, again, our dusty walk toward Dyea. Per Paul’s GPS app on his phone, we’ve now cut off approximately 4 of the 10 miles to the trail head. It’s actually a pleasant walk. The sun is shining and it is far from cold and wet, which is the norm for rainforests of Southeast Alaska. Several other cars pass us and wave, they’re full of gear and bodies (live of course). Another large truck nears us. Let’s see if we (namely I) can Yogi a ride. Yup! A nice Canadian (got his name, but can’t remember it…darn my shortening short term memory) who was on his way to fish the Taiya River for “pinks”, pulled over and offered a ride. “You headed to the Chilkoot Trail?”, he asks. As a matter of fact we are. “One of you is gonna have to squeeze in between the car seats”, he tells us. ‘No problem…it beats walking any further than we have to…today’, we reply. We toss our packs into the back of his truck. In no time we are at the Dyea end of the Chilkoot Trail, where most Stampeders started from in 1897 in their crazed quest for Klondike gold in Dawson. As we unload, he asks if we have bear spray. Of course not, ya think we need it?, we politely ask, knowing full well, that even if he said we were blooming idiots for not carrying it, there was no way in hell we were going into town for a can of bear repellant (as it’s called)…we’ll take our chances being eaten. He says he doesn’t fish without it, as he’s had some close encounters. We tell him that luckily we aren’t going to be anywhere near running salmon so we feel pretty confident that we will be fine without it.

We thank him for the ride (our second dose of “trail magic”) and dub him a “Chilkoot Trail Angel”. “Good luck”, he bids, shaking his head a bit, like “you’re gonna need some luck walking around the woods in bear country without a firearm and/or bear spray…carrying snacks”. We take the obligatory picture at the fancy sign marking the trail. We still have not perfected the art of selfies.

We are quite proud of ourselves at this point, for in a matter of a little over an hour and a half we covered nearly 10miles. Of that 10 miles we only had to walk just over 3 of what we thought would be 10miles. So what could have proven to be a 17 mile first day on the trail, would now only be 10 total miles (3 from town, 7 actual trail miles) This would prove to be a God send as our first steps, and in fact miles on the trail, would prove to be helacious. It of course started with this uphill.

Now how the hell did the Stampeders get their 2000 lbs of “essentials” up this? Oh ya, they mostly did this during winter…or did they?

…to be continued.