Most tailgating takes place on the parade ground, a 12 acre area that forms the center of the VMI post. There is a small tailgate area (maybe an acre or two) in the parking lot at the stadium but this is usually reserved for boosters and alumni groups. I've also seen visiting teams set up tailgate sites on the hill across the street from the stadium but visitors are totally welcome on the parade ground or anywhere on post. To get the full effect of a gameday experience you need to plan to arrive between 9-10 AM to watch the full dress parade of the Corps of Cadets. The portion of the parade ground not used for the parade itself is open to parking and tailgating starting at 0600. The post is open to the public with no security check points but, post 9-11, you can no longer park or drive in front of the barracks and PX area. You can also park in several other areas on post that are a 10-15 minute walk (tops) to the parade ground. The parade usually kicks off at 1030 and is over at 1130 and the cadets are released to go tailgate with family until 1:00 PM when they form up for the march to the stadium and onto the field for the pre-game. It is pretty neat to get to the stadium or get somewhere to watch the march on. Often there is a military fly over or other event accompanying the national anthem.
If you really want the deluxe package, arrive on Friday afternoon and get a cadet guided tour then take in the evening parade at 345-4:30.....there is usually a good crowd hanging out on the parade ground with some grilling - especially on a parents weekend or homecoming.
As an added attraction, last I checked, the mess hall (Crozet Hall)was open to the public for lunch for a small fee (about $5-7 per person i think) before the game and I'm told the food is much improved from my days as a cadet!

Alcohol is officially forbidden and cadets are nott allowed to have alcohol on campus. Having said that....if you put your beverage in a plastic cup, keep the bottles/flasks out of plain view and don't give any cadet "too much" alcohol then you should have no problems. Just be discrete and dont' act the fool.
Also, post 9-11, overnight camping and RV parking are no longer allowed on the parade ground.
Other than that any tarps, games, tents, grills are perfectly fine.

Seats 10,000, standing room 12,000. The place never sells out and crowds of about 9,000 are the norm in the stadium and probably another 1,000 or so watching or hanging out from outside the stadium (there is a hill area with a great view across the road from the stadium that some folks frequent).

Dogs, sausage, pizza, burgers and the usual stadium fare. No booze unless you are a Keydet Club member or a big time donor and can get access to the VIP lounge or the Keydet Club beer tent at the back of the stadium.

There is a TON of stuff do in the area from Civil War history to ghost tours to wineries and vineyards. Shenandoah Valley and Skyline Drive in the fall are world renown for fall colors. Lexington is one of the most historic cities in the US and it is very walkable. A majority of attractions in town are within a 10-15 minute walk from the stadium.

Lee Chapel - Robert E. Lees' Tomb; Stonewall Jackson House and Stonewall Jackson Tomb and historic downtown Lexington are within a mile. The VMI Museum, VMI Chapel and George C Marshall Museum are all located on post within a 5 minute walk of the parade ground.