When I worked as a barista, the owner of the California coffee shop I worked at somehow convinced me to spend two weeks in rural Oregon working at a different coffee shop. Objectively this was not that much fun because I had to drive many hours and rural Oregon is the worst, but I'm glad I went because it kind of started this whole trivia travel lifestyle. I was paid my regular wages, but negotiated a few trivia nights as part of my contract.
Portal Brewing, Medford
This trip was the first out-of-state trivia I ever played, back in 2015 - my boss and I went to two trivia nights and a spelling bee. The first one we went to was a pretty good trivia game at Four Daughters Irish Pub in Medford, the second one was some unremarkable trivia at some unremarkable bar in Ashland, but the real show-stopper was the drunk spelling bee at Portal Brewing.
At the end of the game, I was tied for first with a nice young man named Dennis. The tiebreaker question, we were told, would be a mushroom. I spelled "bridal veil" correctly and Dennis did not - but for his valiant efforts, I named my new car after him. And to this day, Dennis the Yaris reminds me of how good it feels to drink beer and win a spelling bee.