Can race tasks and dates land in my calendar?

Yes. With Google Calendar as your main calendar, your race days appear there as all-day events. Dated race tasks can also go to Google Tasks, which shows them in Google Calendar: switch on Push race deadlines to Google on the Google Calendar page under Settings > Your data. Trailwise asks Google for permission to manage your tasks only at that moment, never when you connect Google Calendar. A task you tick in Trailwise is ticked in Google, and one you tick in Google is ticked in Trailwise the next time you open Race roadmap. If a catalog race changes its date, a watchdog flags it on the card so you can accept or dismiss the change.