Top Definition
The act of taking the gamble and getting shitfaced drunk the night before the Royal St. John's Regatta in St. John's, Newfoundland. Due to the precarious status of the holiday*, this is a risky venture. People may have to go to work with a hangover, or worse: still drunk.

*The Regatta is one of very few weather dependent holidays. If the winds are too high, the boat races are cancelled and there is no holiday. (it will be moved to the following day, weather permitting).
Why is Jane covered in excrement and wearing sunglasses at her desk?

She lost bad at Regatta Roulette.
by townie86 August 02, 2011

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