Carhop service is a classic, just like that car parked in your garage. Unite the two with this food fueled road trip out of the city to Chester's Drive-in in Plymouth. This route from the Harley Davidson Museum to Chester's is a great way to turn a one-hour drive north into two.
Meander your way north from Milwaukee along the lake to the North Shore countryside. You could easily take a little detour into Cedarburg, as you make your way west to Highway 45. Let your car stretch its legs a little on Highway 45 before picking up the county roads near Kewaskum that will wind you back east through the scenic Kettle Moraine to Plymouth.
Chester's is open seasonally, March through October, so you have limited time to enjoy this treat for the taste buds. One unique feature of Chester's is they use fresh ingredients from local suppliers, all served on a tray hung on your car window. Enjoy butterburgers like you can't find anywhere else, served on a Sheboygan County exclusive, the Sheboygan Hard Roll. Wash it down with old-fashioned draft Root Beer. And you can't skip dessert with a classic like the orange sherbet twist cone.
Route: Directions from The Harley Davidson Museum to Chester's Drive-In
Pros: Nice mix of scenic city streets, freeway and curvy country roads. Good duration, about 2 hours one-way.
Cons: If any, that you have to spend some time on the freeway. Though if you are adventurous, have a good map, or are familiar with the area, this could be a completely freeway exempt drive.