By Lilly Milman

It was almost 100 years ago that the first plane landed in Skagway.

The first plane to ever touch down was piloted by Clearance Oliver Prest, who landed on a makeshift airfield near Sylvester’s Wharf at about 3:25 p.m. July 6, 1922.  

An edition of the now-defunct newspaper the Daily Alaskan reported that the beach where he landed had been cleared of sticks and stones and lined with white flags to create a landing strip about 50 feet wide and several hundred feet long. Tourists described Prest as landing in “a most unusual and graceful matter,” according to the newspaper article, which is on dis-play alongside a photo of the biplane, named Polar Bear II, in the Skagway Museum.  

Prest was on a well-reported mission to fly to Siberia, with the intention of writing about his experiences in the remote northern climates. He first flew from Buffalo, New York, to Seattle, before sailing to Juneau and then flying to Skagway. He made stops in Whitehorse, Fort Selkirk and Dawson City, Yukon Territory, and then Eagle across the border in Alaska after spending two days in Skagway. However, his luck turned after he took off from Eagle and engine trouble forced him to crash land 30 minutes into his flight, while on the way to Fairbanks. Unharmed, Prest spent several days in the area and survived on caribou until a search party from Eagle found him, according to the Juneau Empire.  

After Prest, air travel became more common into the 1930s and then, in 1936, Bob Ellis founded the Ketchikan-based Ellis Air Transport. This homegrown operation would soon merge with another local airline, Alaska Coastal Airlines, and eventually became part of Alaska Airlines.  

“(Ellis would) take orders for groceries before flying back to Ketchikan. People would also trust him with their paychecks, knowing he could be counted on to return with carefully identified envelopes full of cash. At Christmas, he’d dress up to become ‘The Flying Santa Claus,’ landing in the villages to pass out candy to the children,” according to a history on the Alaska Airlines website.  

While Skagway, just as the rest of Southeast Alaska, now relies on airplanes for a lot of its goods, the town did not have a paved airfield until the 1980s. The current runway parallel to Alaska Street was a dirt field built in 1950, paved 30 years later, with a taxiway added in 2000. 

Currently, Alaska Seaplanes is the only year-round airline serving Skagway since Wings of Alaska was shut down in 2017. Husband-and-wife duo Paul and Amy Swanstrom have been operating the flightseeing company Mountain Flying Services based in Haines and Skagway since 1992.

As a pilot with 27 years of experience, Paul Swanstrom has seen a lot of changes, particularly in technology. 

He said flying in Southeast Alaska is more challenging than in areas of the Lower 48 because of the climate and the low visibility in the mountains, but GPS technology has made it much safer in recent years. 

“Before the advent of GPS, you were pretty limited if you got into the clouds,” he said. “It’s much easier now, but you still have to keep the plane upright.”