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I've always assumed that Hearts and Hooves Day happens around the same time as Valentine's Day does in real life (in the Equestrian equivalent of February). However, the episode and song "Winter Wrap Up" would have us believe that "tomorrow spring is here", and that snow is all over the place between the Running of the Leaves and Winter Wrap Up every single year... and this creates a problem. To explain simply, the timeline of this states:

  1. After the Running of the Leaves on the Winter Solstice, snow covers everything all winter.
  2. Soon after, Hearthswarming Eve is celebrated.
  3. Almost two months later, Hearts and Hooves Day is celebrated. During the episode focusing on this, there is no snow present.
  4. Winter Wrap-Up occurs about a month after Hearts and Hooves Day on the Vernal Equinox.

I'm sure you can spot the issue. If Hearts and Hooves Day and Valentines day are one in the same as I initially thought, then that means it would take place prior to the Vernal Equinox, so the episode should have snow everywhere! But it doesn't.

So, when the heck DOES Hearts and Hooves Day happen? It can't happen in summer (no school)... so...?