I speak from some experience, as one of the jobs I worked to keep myself in college in Pennsylvania back in the 70's was as a driver for a state beer distributor.
Vetoing Liquor Privatization, Pennsylvania's Governor Says Competition Would Raise Prices
I dislike to point out the obvious mental and moral weaknesses of my societal betters...no, wait, I do like it...but one of the challenges at our state operated beer distributor was that we bordered Ohio and people, including bar owners, would simply jump over the state line and purchase stock that was up to 40% cheaper and much more varied. That was wildly against the law, of course, but there's a certain thrill to sneaking across border country farm roads in the middle of the night with a pickup truck full of Stroh's and Carling Black Label.
Naturally, not only did this take from the revenue expected by Pennsylvania, it required expensive monitoring by law enforcement. The danger of being pulled over and cited by the Pa. state police was always a reality.
In fact, during my days at the monastery in Pennsylvania, which was literally a stone's throw from New York [no kidding, one could stand at the front door of the monastery and hit the "Welcome to New York" sign with a stone], we would purchase our sacramental wine from a liquor store in New York that was only five miles away rather drive fifteen to the official Pennsylvania store.
If you want to press Americans into becoming outlaws, simply constrain their freedom.