A "worst" bike ride?? You must be kidding!!
Well, the very FIRST ride (4 years ago) on my new mtn bike (never having owned one before) I thought, "I can go anywhere and do anything" with this bike. So, off I headed, cross country (literally) through weeds and brush.
Of course, no tube, repair kit, no nothing. About 5 miles out goatheads all over the wheels, tubes flat, tire coming off of the wheel rims.
Had a nice 5 mile hike carrying a bike that day!