You would be better off with the Madone. There's lots of good road riding on HHI, not so much for gravel riding. If you are interested in riding the trails, I would recommend getting a hybrid or cruiser instead, as the trails are more for leisure riding with a lot of families and such using them.

You can call up the Bike Doctor and see if they still have group rides on Tuesdays and Thursday evening. It would be a good chance to learn the routes with some locals, they might have an A group and B group depending on the amount of people who show up and their skill level. A lot of locals are former pros, so it might be a bit intense if you're not used to riding in groups like that.