Hi Heather! Thanks for the note. At this point unfortunately neither of these are possible; basically the map integration as it stands is limited to being on an event-by-event basis. We may integrate with a map tool down the road that allows for this (one mashup calendar showing all events in the calendar or in a given category), and we even had our own Geo Tagger plugin out there for a while that has since ceased functionality. But our eventual plan is to rearchitect that so it works nicely with The Events Calendar so you can accomplish this that way.
In the interim, you may be able to find a third-party plugin that can do this. Since events are just a custom post type, a plugin that works for mass mapping regular posts should generally work with Events as well (though no guarantees there). Sorry I couldn’t offer up something more substantive here. Let me know if you have other questions!