Thank you Wizard! That info helped me realize the Freedom Trail lot wasn't exactly what I had in mind, still want to try it but, I am curious about the parking lot that intersects with the Bowen Ranch Trail after about .5-1 miles on it. The lot is a couple yards east of the trail and I've always seen at least one car there. From an aerial map it looks like theres a way to it from the upper bowen ranch parking area(which I'm guessing is blocked?) and then another way if you take a left off of Bowen Ranch Road a little earlier but this might be a private resident's way in? I've attached an image with the route traced in green and the bowen ranch trail in red.

https://image.ibb.co/cRgoKc/offroadmap.jpg