There are lots of people who have jeeps and use them offroad in the GTA. There are no legal trails in the GTA but the cloest are in Bobcaygeon. If you're not already a member consider joining the OF4WD. As a member you will have access to the online trail index and learn about other events. Unfortunately the 2 larger events near Toronto have both sold out for this summer.
2003 Jeep TJ Rubicon