…We toured also during those decades, including an eight-week cross country cycling honeymoon from Los Angeles to Washington DC. I'm doubtful she [my wife] would want to go back to touring,but might want to participate as follows.
When I win the big lottery, I want to buy a luxury RV as my sag wagon and cycle the perimeter of the country, so I’ll need a driver.
I have daydreamed about it to the extent of defining the perimeter as riding within 50 miles of the border all around the country.
The only other definition I know of is in the motorcycle community,where I have read the definition as traveling from the cornermost towns in the country. This would obviously be a shorter route since it would bypass the additional contours of Michigan, upstate New York, and Texas.
I'd like to try for a continuous ride: starting in Boston around September and down the east Coast to Florida in December; across the South through to March or April, the West Coast to June/July (though North to South is apparently the preferred direction), then across the North in the heat of the summer (or start in Boston in around June or July for the counterclockwise route).
In the course of my fantasizing, I have discovered
The Perimeter Bicycling Association of America Inc.which maintains perimeter cycling records for various political and geographic entities. For the USA, the record is 12,092 miles in 180 days held by Richard DeBernardis (date not specified).