Stir liquid ingredients with ice. Pour into an old fashion glass with large cube of ice. Garnish with three olives on a cocktail stick.
The drink starts with a gentle waft of sweet spice and ethanol. The flavors seem to hit all of the senses at once with spices from the rye and Ramazzotti and citrus-like sweetness from the Gran Classico and Campari. You are finally left with vegetative bitterness from the various amari.
As with most drinks, I start with a kitchen sink approach with everything being thrown in, and slowing removing the unnecessary or unwanted parts. In this case, the basic Boulevardier was changed to incorporate more flavors. The Campari was split with Gran Classico to allow other favors to be noticed. The Ramazzotti and Cynar replaced the red vermouth, because they bring more flavors to the party. In the end, the drink becomes an amari bomb.
The name is a combinations of spoofs and obtuse references. 'Wisconsin' was used, because the folks there always add olives to a cocktail. 'County Road' was used as a reference to boulevard...ier (ha,ha). And 'Double Y' is a rhyme with Double Rye whiskey. The county roads in Wisconsin use double letters to identify minor roads such as YY, aka Double Y. So, in the end, this drink is meant to remind you of a pleasant drive on a rustic road.