The “Christmas Pickle” supposedly originated in 1800, when Woolworth stores in America started selling glass ornaments imported from Germany.
Among the fruits and vegetables mixed into the decorative medley was a pickle—and around that same time, the story spread that the Christmas Pickle was an old tradition where it was to be the last ornament hung on a Christmas tree, and the first child to spot it would get an extra present.
Another story took place during the American Civil War, where Private John C Lower was captured and taken to a prison camp. On Christmas Eve, he begged the prison guard for a pickle as he was starving, and that one pickle ended up giving him the strength to survive. After returning home, he began a tradition of hiding a pickle in the family Christmas tree every year.
There is also a completely different version, a medieval story that some think might be the origin of the Christmas Pickle.
St. Nicholas had been passing through a village on his way home when he stopped at an inn for a night, not knowing the evil innkeeper was keeping a villainous secret.
The innkeeper had apparently stuffed two Spanish boys, on their way home from boarding school, into a pickle barrel and left them for dead. But St. Nicholas happened upon them, and brought them back to life.
In any case, whether any of these stories are true, or that pickles just seem strange enough to need elaborate justification before setting on a tree, the Christmas Pickle is a fortuitous symbol for those who still uphold the tradition.