Have you hiked the area? Are there trails? With trails, it would be OK. But you will find it harder/slower than running on the roads. The run/walk concept is most important to a gradual introduction to running. It can be done as well on trails as on the road. Without trails, I wouldn't recommend it for a beginner. Boots? You probably don't need boots, unless you're trying to protect your lower legs against something like snakebite. A good pair of trail running shoes should provide adequate support.
I do a lot of hiking as well as running, and I'd hesitate to do a run, even on rough terrain, in hiking boots. They'd provide plenty of ankle support and traction, but it would also be the equivalent of running with ankle weights, and would put a lot of extra stress on your lower leg joints. Not to mention that they'd also keep your feet and ankles from flexing normally during a run.
Heart of the City Run, Los Angeles, CA, 24:13
Downtown Anaheim 5K, Anaheim, CA, 24:32
Claremont Turkey Trot, Claremont, CA, 24:20
The Great Race - Old Agoura 10K, Agoura Hills, CA, 51:12
Fiesta Days Run, La Canada, CA, 49:31
LA Cancer Challenge, West Los Angeles, CA, 51:21
Long Beach International City Bank Half Marathon, Long Beach, CA, 1:54:31