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With Java and Perl background, I have narrowed down the web framework choices to Grail or RoR.

The web application is a highly interactive content management app ran on private cloud.

One vision is to make all the widgets on the web pages to be event driven: click, double click, right click, keyboard shortcuts, etc. Does either framework supports this?

A: 

Both Grails and Rails will be able to provide the backend support for what you are looking to achieve. Frontend matters such as click and double click will require you to weigh up client side technologies such as Javascript, Flash, Silverlight etc.

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+1  A: 

I have developed with groovy on grails and ruby on rails. You can do highly interactive AJAX work with either of those frameworks - it won't matter which.

Scaling the application has more to do with caching, fronting the application with a high-speed web server for static content and that kind of thing.

When it comes to making a straight choice between grails and rails I'd consider two things:

  • which of grails and rails are you most familiar with?
  • do you have any legacy Java or Ruby code you need to integrate with?

Apart from those two considerations, there isn't much to choose between them.

cartoonfox