STORY OF SEASONS: Pioneers of Olive Town

This is for pulling 50 different instances of planted crops out of the ground, not for having amassed 50 crops during a harvest. For instance, if you pull up a crop and get 3 different crops, it's only one harvest. I do not know if this counts harvesting any of the wild crops that appear throughout the seasons growing on the untilled ground. If you'd like to check your progress towards this trophy, or other cumulative types:

1) On the Title Screen, go through the trophy icon to find all tracked trophies. Trophies with cumulative progress can be tracked from here.
2) In-game, go to the Records page of your menu and choose Change Title. Interact with the Fieldwork option and you'll see, among other progressive title unlocks, this specific one.