If you are fortunate enough, you might already have your twitter archive.
And if you set up Tweet Nest on your server, you might enjoy this little php snippet.
This is basically a more usable version of Memolane’s Memomail.
It fetches the tweets from 1, 2 and 3 years ago from your Tweet Nest via curl, removes everything but the header and the tweets and sends you an HTML mail.
You can set this up with a cronjob for automatic mails.
This snippet is roughly commented and not documented.
I just wanted to share this for you to build upon.