How are harassment/restraining orders served to an individual in the state of Massachusetts?

They have to be personally served.

Is that what you are asking? This leads me to believe that the Police serve the actual Order if the person is not present in Court: "A restraining order is valid as soon as a judge issues it, but violation of a restraining order cannot be prosecuted unless the abuser knew about the order when the violation happened. For this reason, when applying for a restraining order, if the defendant is not present, it is very important to provide the court and/or the police with any information that will help locate the defendant.

If the order is violated, police should be notified and the victim should tell the police anything that leads her to believe the defendant knew about the order. Regardless of what court issues the order, it is valid throughout Massachusetts, and in most other states, until the expiration date listed. If a victim moves out of Massachusetts, some states require registration of the order with the local police department."

http://www.crimevictimlaw.com/restrain/restrain.html