The Cruise of the Bigler is a fresh-water sailing song. Great Lake voyages did not have the length of clipper trips, but the storms were sufficiently deadly. Work was plenty and recreation was still required as well.
Skillagalee is Isle aux Galeta. Wabbleshanks is Waugoshance.
Sweepstakes could refer to one of several Great Lakes tugboats: [1] or [2].
Frank Shay gives a complimentary version by Captain Asel Trueblood of St. Ignance, Michigan, which can be found in the Archive of American Folksong in the Library of Congress. Trueblood explained to Alan Lomax (1915):
I learned this song a good fifty years ago. I was twenty-three at the time. I’ve walked the old Bigler’s decks many times though I never sailed on her. She was supposed to be the slowest vessel in the fleet, and, of course, they had winds and all that and she’d bile along like everything but the other vessels would beat her. They stopped many places on the way down, and a new verse was composed about every place they stopped in and every place they’d pass. And when they got done in Lake Erie, before they got to Buffalo, they met the fleet coming back.
I knew this feller that composed this song about the Bigler, but I forgot his name. It was a kind of a jokey song like, because they got beat. He said they’d a’beat the fleet if the fleet had a’hove to. The places they stopped in were the whorehouses on the way down, and they’d get in there drinkin’ beer and singin’ this song, and it bought ‘em a lot of free beers.
A clipping from the Toronto Telegram, Oct. 3, 1942, gives much more information about the ship and the song. The earliest surviving source seems to be due to Emilius Jarvis who recorded it for his sister when he was on the timber drogher Edward Blake in 1875. The chorus is evidently borrowed from a fortyniner goldrush shanty.
Eckstorm and Smyth describe in Minstrelsy of Maine (1927) that the chorus was also used as a lumber shanty with locally-composed verses. The title given is Buffalo.