ClassiPress is designed as a classified ads theme and does not have a calendar built into the theme, but I have seen a modified version of ClassiPress which was used for events/directory purposes. You could either customize the theme yourself to fit around your requirements, or possibly look at using both the
ClassiPress and Vantage themes on one site to offer all the functionality you're looking for. Vantage is our business directory theme, and events functionality is planned for the next major release.
So, what I mean by using both themes is that you could set up in a separate subdirectory:
e.g.
yourdomain.com <= Your Vantage installation
yourdomain.com <= Your ClassiPress installation
And perhaps look at a
WordPress multisite installation to manage user accounts across both themes. Thanks.