The vehicle in the drawing is an automobile built by Robert. E. “Bobby” Sheldon at Skagway in 1905. Bobby was born in Snohomish, Washington, in 1883. In 1897 he and his father landed in Skagway, headed for the Klondike. Unfortunately, his father suffered a heart attack ascending the Chilkoot Trail and returned to Seattle, leaving 14-year-old Bobby in Skagway.
Bobby supported himself at first by selling newspapers, with Soapy Smith being one of his regular customers. He later worked on the Bracket Toll Road (George Bracket was the developer). The road predated the White Pass and Yukon Route Railway (WP&YRR), and was the first effort to improve William Moore’s rugged pack-horse trail (nicknamed the Dead Horse Trail) over the White Pass.
Bobby had a natural affinity for mechanics, and moved on to maintaining the engines of small steamers plying the waters between Skagway and Juneau. He eventually worked for the WP&YRR, and then Skagway’s power company.
In 1905, while working for the power company, he became enamored of a young Skagway lady. Another of the lady’s suitors was the son of a wealthy area resident and had the use of his father’s horse and fancy buggy for courting. Bobby, trying to tip the odds in his favor, decided to impress the girl by building from scratch “one of those new gasoline powered buggies” he had been reading about. He stated in interviews that he had never seen one in person, having only looked at pictures of, and read about automobiles in magazines.
With a paucity of funds, he assembled an automobile using railway baggage-cart wheals, a home-built frame and body, two stools from a saloon, a two-stroke marine engine salvaged from a derelict boat, some gears and bicycle chains cobbled together into a drive line, and miscellaneous other scrounged parts. Not wanting to look the fool if his creation was a disaster, he tested it in late-night solitude. The auto ran, it’s speed topping out at 15 mph.
His auto did not sway his intended girlfriend, though. She allowed Bobby to give her a few rides around town in his auto-buggy, but she married the other fellow.
Bobby’s auto is touted as the first automobile built in Alaska, but many people also assume that it was the Territory’s first automobile. However, historian Nancy Dewitt has written that prior to 1905 several gas-powered motor vehicles passed through Skagway on their way to Dawson in the Klondike. If any of them were driven under their own power from the docks to the railroad station, they could claim the distinction of being the first automobiles in Alaska.
Its allure as a chick magnet dashed, Bobby’s auto wasn’t driven much after that first summer. It was put in storage and in 1908 Bobby moved to Fairbanks. He did not leave his enthusiasm for automobiles behind though. In 1913 he bought a Ford Model T and had it shipped to Fairbanks. Later that year, after earning money driving passengers around the Fairbanks area, he became the first person to drive an automobile over the trail from Fairbanks To Valdez. He later owned an auto stage line, and then managed the bus concession at Mt. McKinley National Park (now Denali National Park and Preserve).
In 1934 Bobby donated his Skagway creation to the University of Alaska, and it was shipped to Fairbanks. Where exactly it spent the next few decades in uncertain, but in 1972 it was moved to the university museum, where it was on display for over 30 years. It is now on loan from the University to the Fountainhead Antique Auto Museum. Bobby’s auto-buggy can be seen at the antique auto museum’s location in Lemeta.