Sadly, the short answer is that you can't have it all. Either you index the separate calendar pages, get more pages/content out there and risk some "thinning" of your index, or you focus on one page, maximize the SEO value, but then lose the individual pages.
I would not 301 or 302 to the individual calendar URLs - that kind of daily URL shifting is going to look suspicious, Google will not re-cache consistently, and you're going to end up with a long-term mess, I strongly suspect.
I actually tend to agree with Muhammed and Paragon that a viable option would be to let the individual days have their own content, but then canonical to the main calendar page to focus the search results. That way, users can still cycle through each individual day, but Google will focus on the core content. In a way, that's how a blog home-page works - the content changes daily, but you're still keeping the bots focused on one URL.
Think of it in terms of usability, too. How valuable is old/outdated content to search users? They might find something relevant on an old page, but they still probably want to see the main calendar and view recent content.
Where are the links to the individual days, if "/calendar" always has today's content? I'm wondering if there's a hybrid approach, like letting the most recent 30 days all have their own URLs, but then redirecting or using rel-canonical to point to the main page after 30 days.