Usually. I have had somewhat mixed success myself with this. Most of the time, when a second monitor is attached, a simple power cycle off and on of the monitor will get Windows to spot it and start it up if it isn't recognized immediately when plugged in. However, sometimes I have had to do a full reboot to get it to recognize.
However, I should also note in the interest of completeness that it is generally considered not a good idea to plug and unplug monitors while your PC is powered on. Monitor plugs are not considered "hot swapable" like USB or Firewire or Ethernet would be. While the potential is very small, there is the potential of power surges or static discharge which could potentially damage your video card. I've never had this problem nor had it happen to friends, but the potential is there.