Windber is a large gathering of mini bike enthusiasts. As you've seen, folks come from all over. Most of us talk bikes, share stories, laugh and zoom around the field, track or the trails. Wednesday PM to Saturday morning you've got good people who are respectful of the property and the Milhakos. Two years ago, some kids were pretty obnoxious on their minis/Warriors and ignored the rules. It was so rainy and muddy that the kids tore up a good part of the access road and the lower field area. So, some rules got changed. By and large, parents policed their kids pretty well last year. Most adults behaved though a couple individuals were banned.
My observation is this....Saturday morning is when the "rowdiness" begins. People arrive to participate in the parade, pay their registration fee (maybe), and ignore the rules. That's when the stupid stuff starts. The Milhakos banned riding after the parade for a couple hours because of an accident on the ride back. Some folks ignored rules of the road and one paid a price for it.
As to crossing the border with bikes in tow, Big Rob is probably one to talk to. I can tell you that you'll need your passport and IDs. One of my friends here is permanent US resident Canadian, went on vacation with his significant other and didn't have his green card. Almost had a major issue with the Border Patrol.
So many of us are late 40s through our 60s. We know how to act properly. It's the day trippers that ruin the experience, in my opinion.