Looking for a place or 2 to go trail riding in Hampton roads and not be trespassing. nothing too crazy, i don't want to break anything yet.
I wish you the best of luck. I spent over 35 years in the 757 and there is narry an actual trail to be found. Ever since Dominion/Vepco cracked down on the power line trails 10 or so years ago there just isn't anything public.
Few things.
Starr motors in Suffolk has an off road club and does public trail days. There is one that is open to anyone with 4wd, there is one that is sponsored by the VA4WDA (also open to the public), and they usually do something around labor day. They have a meetup group that posts all the information.
The dealership has a "proving ground" of sorts behind it that backs up to 58. It's like two main trails with some fun obstacles. A decent rock garden and some pretty big hills. I was able to take my trucks there at least twice a year and stretch their legs. It's not big, but it's fun for an afternoon plus you get to see people in big shiat do things that break stuff.
Your only other two options are the GWNF just outside of Harrisonburg (3hr drive) or going down to the outer banks and drive on the beach.
I will say that if you take 12N (left just past the Wal-Mart on 168 in Nags Head) and take that all the way up through Duck and Carolla, 12 just turns right and dumps onto the beach. That is Carova Beach. It goes all the way back up to the VA state line. The first 12 miles are just beach road. You're on the beach but driving traffic only. Once you pass that you can park on the beach and chill. You have to park in the middle of the beach. Just remember the speed limit and beware of kids. That place gets swamped in the summer.
The fun part about Carova is once you get to the neighborhood, you can drive behind the dunes and there's a bunch of trails back there. Lots of places to get lost and SOME REALLY deep rain water puddles. I've seen lots of people hydrolock engines on those trails. But it's fun. When I lived on that coast, Carova was the only place I'd even bother to go to the beach.
I've got some old YouTube videos I'll have to dig up to show you what I'm on about.