Get a fresh newspaper which can be found outside of your front door and then select "Check Weekly Events". A new newspaper is delivered everyday. At the top right of your screen it will pop up with all the events coming up. Press and then check the location, day, and time of the event. Wait until the right time to attend the event and press and go to the "Town Map". Find the place you need to visit and go there. After the event is complete the achievement will unlock.
Here is an event you can do any time:
Event: Amateur Olympics
Time and day: Saturday from 8:00 AM to 5:00 PM
Location: Bay Memorial Stadium
You only have to attend to unlock this achievement.