there are a few groups in the area, http://clubs.jeepforum.com/State/Virginia/
You arent going to find any trails around here, gonna have to head out west into the mountains, there's also a place in NC not too far from here. My club is based more in northern va even though i live down here, but good group of guys and we have cookouts occasionally and camping trips often. Hit our forum up and say whats up maybe you can make a trip or come out to a BBQ
Dad- '08 JK Rubicon- Stock, BB and 33s coming
Sister- '07 FJ Cruiser- Rear locker, BFG A/Ts VT
the apartments im in now in richmond used to have a nice little 2 mile or so trail behind them. the apartments were built like 3 years ago and they had cleared a nice little trail out in the woods behind them in preparation for new houses and everything, but since they started construction on them about 6 months ago I don't know of anything between here and the beach area. I know a couple places in NC but thats about it.
the only trails i know of are out west in the mountains such as george washington national forest and i have heard of a few in NC. if you find out of any others specially if they are closer let me know i have wanted to go i have never been on a trail yet.
Our club "Middle Penninsula Jeep Assoc Inc"(MPJAI) is in Newport News. We have Coffee Run "get togethers" every Saturday. We also do monthly wheeling trips. I think we're going to hit a local Jeep dealership obstacle course in a couple weeks. It's a lot of fun. The course has stuff easy enough for stock vehicles and tough enough to challenge well-built rigs.