Well, next month I'm doing YYT-YYZ-YVR-SYD-SIN-BKK-HKG-YYZ-YYT over the course of two weeks. Not a mileage run but a biz trip. Going to Asia/Oz from the East Coast invariably means 2 stops before you actually go TPAC. The only superfluous bit of my intinerary is the stop in BKK. Our TA can't get me biz class on SQ so currently I'm routed on TG via BKK. I'm hoping she can change this as I'd rather miss out that extra stop.
The best routing story I had was my MiL who rather foolishly tried to use an airline standby ticket (one of my BiL's works for an airline) for Easter travel YYT-YHZ. When she was told she had no hope of getting on a plane to meet her planned flight for YHZ to mexico for a wedding/vacation she had to buy a massively expensive ticket that took her YYT-YDF-YYR-YHZ. That's a very scenic route.