Hua Hin's biggest event (quite literally) is elephant polo. Held at the Pradiphat Pine Forest at Suan Son south of Hua Hin the tournament attracts teams from all over the world. Other popular events include a local jazz festival and the Hua Hin/Cha-am Golf Festival. For timing of these events it is best to check with the Tourism Authority of Thailand as the dates move around.
The whole area really takes off during national holidays when Bangkok seems to arrive en mass at the resorts. Getting rooms at these times can be almost impossible. The Kings Birthday (Dec 5), Songkran Water Festival (April) and all the major public holidays especially around Christmas, Chinese New Year and Easter are very busy periods.