There's a big difference between listing Rails (a new technology -even rails 1 is a new technology- that is currently widely used), and listing COBOL. Don't even bother listing cobol/perl/whatever unless the company you are using uses those technologies.
But your bigger point - yes - have modern skills, and being able to show those with relatively current tech is the best way to go. Personally, I'd take someone who is older but within a few years of current tech vs less experiences with only modern tech. 8 years of Java and Ruby with experience up to Rails 3 vs 1 year of Rails 4 only? Should be a no brainer for most situations, unless the job is "writing Rails 4 tutorials" ;)
There's a huge spectrum of middle ground there, and good companies/recruiters should be able to divine that. ("should" being the operative word).