<SHAMELESS PLUG>I live in Hampton, and am a member of Middle Peninsula Jeep Association. I strongly encourage you to mosey over to mpjai.com and register on our forum. Its free and without obligation (I have the same nick over there). We are a bit far from the beach, meeting at the Dunkin Donuts on Jefferson in NN every Saturday morning to shoot the bull
We also have a monthly meeting at the Pomoco near there. Anyways lots of useful info and peeps on the club forum. Mention my nick when you register!</SHAMELESS PLUG> Anyways, you might also want to check out Tidewater 4Wheelers, Starr Motors Offroad Club, or KMA. There used to be a VB club but I don't think they are around any more.
Anyways, there isnt much for trails on this half of the state. Starr Motors in Suffolk has a small offroad course behind the dealership that they open every now and again. That is about the only local legal place. Everything else is 3+ hour drive. You just missed a club run down to Corolla Beach yesterday!