A challenge cribbage game comprising a cribbage board having at least two parallel player routes of 122 player holes along a path from a start position to a finish position, a single player hole at the finish position, and a plurality of challenge holes adjacent specific player holes along the parallel routes; providing a standard deck of cribbage playing cards; at least two pairs of matching player pegs and at least six additional challenge pegs; a list of challenge conditions, each corresponding to a challenge peg; placing each pair of matching player pegs in the first two holes of each player route; placing each challenge peg in a selected challenge holes; commencing game play consistent with the rules of cribbage; and varying game play from by following the directions of each challenge each time a player peg lands in a player hole adjacent a challenge hole containing a challenge peg.