Cycling Through History in Skagway and Dyea

Tuesday, June 23, 2015
Today, Princess Cruises’ Star Princess arrived at our first port of call since setting sail from Seward three days ago: Skagway, Alaska.
In 1896, Skagway was nothing more than a few modest trapper’s cabins. By 1897, it was a rapidly expanding town and by 1898 it was the last frontier in a very new, and very competitive, Wild West. Sam Steele of the Royal Canadian Mounted Police likened Skagway to “little better than hell on earth” thanks to the con-men, good-time-girls and various scams and pratfalls that frequently befell prospectors looking to sail into the sunset with their winnings from the Klondike Gold Rush.


The most notorious of these con-men was Jefferson Randolph “Soapy” Smith, a con-man from Denver who ruled Skagway with an iron fist. In addition to running a large racketeering ring in Skagway, Soapy would “relieve” early prospectors of their earnings through a series of rigged table games held at Jeff Smith’s Parlor, a modest structure that still stands today in Skagway. Soapy even had telegraph lines that ran only as far as the wall; perfect for sending that drunken expression of love to a recipient who would never get it.
Soapy Smith was killed in a gunfight out on the wharf in July of 1898. Reportedly, his last words were a very mild, “My God – don’t shoot!”

Smith also reportedly had control over another place: the nearby town of Dyea (pronounced dye-ee). Built further north on the upper extremities of Lynn Canal, Dyea is but a few dozen miles from Skagway. It flourished during the height of the gold rush in 1897-98, but as quickly as it went up, it was also abandoned. Facing a shallow-water port and the lack of rail connections through the newly-built White Pass & Yukon Route railroad that ran through Skagway, Dyea was largely abandoned by 1905.
And today, I got to cycle through the remains of the town.

Princess offers a great “Rainforest Bicycle Tour” that spans three hours in duration. Booked through Princess either before your cruise or while onboard for a cost of US$99 per person, it picks guests up straight from the pier in a van equipped with bicycles and all the necessary gear. From there, you’re driven just outside Dyea to begin your moderately-strenuous cycle through the forested remains of the town and the flat clearings that border the ocean.
After breakfast, I disembarked the Star Princess in order to be pierside at the requested time. I met my guide (who, conveniently was named Erin), and I casually stood there waiting for what I assumed would be a five or ten minute wait for the rest of the guests. Erin started walking. I stayed put.
“Ok,” she said. “We can go now.”

I looked around. “You mean I’m it? I’m the only person on a 2,600-passenger ship that wanted to do this?”
“I guess so!” she said. In fact, we made a stop off first to pick up two other guests who were also from the Star Princess but who had made their way to the cycling company’s offices a few blocks away. So, there were three of us. Just three. I was a little disheartened to see that. I want Princess to keep offering active excursions like this in port, and I’d like to see more people do things like this.
However, our low numbers turned out to be a great thing. Plus another girl who lived in town and booked independently, there would only be five of us on this cycle, including our guide Erin. Having a small, intimate group like that allowed us to spend more time cycling as well as more time stopped admiring the scenery. We passed several larger groups with a dozen or more people; our small group was far more nimble.

What we were treated to was a fantastic morning. If you can ride a bicycle over a distance of approximately five miles (eight kilometres) on mostly-flat land (there are one or two very gentle inclines and some cycling on dirt and gravel service roads), then you’ll greatly enjoy this excursion.
Seeing the abandoned ruins of Dyea really helps to gauge just how quickly these towns sprang up – and how fast Mother Nature has reclaimed this land. But for the railroad and steamship traffic, Skagway would have ended up like this, too.
Some photos of our great cycle this morning:




The only disclaimer: bring the strongest insect repellent you have. I literally had to put on a light windbreaker and douse it in OFF! Because the spray I was putting on my exposed arms seemingly had no effect. The mosquitoes are intense in Alaska.
Following my excursion, it was back onboard Star Princess for a cappuccino at the International Café, plus one of the café’s light bites to tide me over after my morning of exercise. Then, it was time for a stroll through Skagway.

While I enjoyed the streets of Skagway as I always do, the one fabulous discovery on this trip was the Skagway Brewing Co. Located on 7th and Broadway (which is very nearly at the commercial end of Broadway), this brewpub offers up some delicious food and some great, locally-made beers.
My personal favorite: the Spruce Tip Blonde, brewed with hand-picked Sitka Spruce tree tips. The taste, especially on a hot day, is unbelievably good.
Some photos from our time ashore in this fascinating ex-Gold Rush town:







Tonight, we took some time to do a little cocktail-tasting in Crooners, Star Princess’ dedicated martini and cocktail bar situated on Promenade Deck 7 adjacent to the central Piazza Atrium’s uppermost level.
Today’s Drink of the Day: the Skagway Spiced Apple, which has become a fast favorite of mine. Made with Bacardi Oakheart Spiced Rum, hot apple cider and lemon juice, it’s on special today for $8.95. But Crooners offers a vast array of cocktail and martini libations, along with a small selection of beers and wines if that’s your thing. But really: you come here for the martinis and the live music.


Tonight, there is live music in Crooners at 7:30 p.m. with guitarist Henry Hood, and again 8:30 p.m. with singer and pianist Bert Stratton.
Live music is one of Princess Cruises’ greatest strengths. It’s happening all around the ship tonight, from the Piazza Atrium on Deck 5 all the way up to the BOGO (Buy One Get One drinks) antics that typically close the night up in Skywalkers on Deck 18 with DJ Robbie.
It’s just another great evening here onboard the Star Princess – where there really is something for everyone to enjoy.

Star Princess, Denali Explorer
Day 1 & 2 | Anchorage & Mt. McKinley |
Day 3 | Denali National Park |
Day 4 | Double Denali |
Day 5 | Boarding the Star Princess |
Day 6 | Hubbard Glacier |
Day 7 | Glacier Bay |
Day 8 | Skagway |
Day 9 | Juneau |
Day 10 | Ketchikan |
One Comment
Thanks for your ride review. I am looking at this excursion the end of Aug 2019 (YES it is still offered by Princess). Debating over the 15 mile downhill ride and this one. Your review was very informative. Found you just doing a google search for images of Dyea.