I know some "old" resources, but I think there's still a lot of interesting things to get out of it:
Back in 2010, I discovered and learned both Ruby and Sinatra through Darren Jones and his series "I Dit It My Way", or "The Sinatra Songbook Project" : ididitmyway.herokuapp.com/ (I even translated it into French)
There was also "Sinatra: Up and Running", a book written by Konstantin Haase who maintained the Sinatra project at the time: shop.oreilly.com/product/063692001...
I know some "old" resources, but I think there's still a lot of interesting things to get out of it: