We have experienced this same issue. First off, install the mongrel_proctitle gem
http://github.com/rtomayko/mongrel_proctitle/tree/master
This gem/plugin will allow you to view the mongrel processes via "ps" and you can see if a Mongrel is hung. An issue we have seen with Mongrel is that it will happily accept connections and enqueue them, then wedge itself. This plugin will help you see when a Mongrel has been wedged but then you must use another monitoring app to actually restart a a wedged Mongrel, something like Monit or God
You might also want to consider putting a more balanced reverse proxy in front of your Mongrels, something HAproxy, instead of nginx, Apache or Lighttpd. With a setting of "maxconn 1" in HAproxy you can assure that the queue is being maintained by HAproxy versus Mongrel. The other reverse proxies (nginx, Apache, Lighttpd) only do round-robin which means that they can load up your Mongrel queue, inadvertently.
My personal choice is God as it is much more flexible.
tl;dr Install this gem plugin and keep an eye on your Mongrels. Try Apache+Phusion Passenger.