This updated printing of the first edition of Colorado Mathematical Olympiad: the First Twenty Years and Further Explorations gives the interesting history of the competition as well as an outline of all the problems and solutions that have been created for the contest over the years. Many of the essay problems were inspired by Russian mathematical folklore and written to suit the young audience; for example, the 1989 Sugar problem was written in a pleasant Lewis Carroll-like story. Some other entertaining problems involve olde Victorian map colourings, King Authur and the knights of the round table, rooks in space, Santa Claus and his elves painting planes, football for 23, and even the Colorado Springs subway system.