If you've never attended a poker run, toy run, or any of the other type rides frequently held by motorcycle groups, you may not be sure what to expect. For starters, the rides listed on the VirginiaWind calendar are generally open to all motorcyclists, and I've never attended a ride yet where any of the organizers or the participants were less than cordial. You'll be welcomed, so don't sweat that part.
Upon arrival find the check in person who will probably have you sign a waiver of liability, and ask for a $10 to $20 dollar fee. Part of the fee may go to prizes, but normally most of it will go to a charity. If it's a poker run, you'll also get a sheet for recording your cards, but you can learn more about those at "Poker Runs". Many runs will also have a 50/50 drawing. This is a game where you pay $1 and get half a ticket. The other half goes into the hat and at some point in the day someone draws from the hat and the winner gets half the money collected. Again, the rest of the money normally goes to the day's charity. It's not uncommon for the winner to donate their winnings to the charity, but that's entirely up to the winner.
Depending upon the number of attendees, the ride may be broken into 2 or more groups for safety and ease of management. You can expect to be riding in formation, and communicating with hand signals, so familiarize yourself with both before departure (the ride captain may review them, so pay attention to any differences). Many times you'll be given a route sheet to follow, and it's a good idea to keep it handy in case you get separated from your group. It's also a good idea to have a map or GPS with you in case you get really lost (voice of experience maybe?).
You should be prepared to ride somewhere between 75 and 150 miles on the run, so make sure you start with a full tank of gas, an empty bladder, and a mechanically sound machine. You will, however, be stopping along the way to top off your tank and take care of any necessitates, so don't worry too much about the distance. Do consider how far it is to the start of the ride, and how far you'll need to ride to get home in estimating your distance for the day.
At the end of the ride there may be prizes, food, drinks, music, etc., but those are secondary to the reason to go. The primary reason is that you'll have a nice ride, meet new folks, and know that you've contributed to something worthwhile.