Brown Deer
vs.
Waukesha
 
Year Founded: 1955
Population: 12,000
Scouting report: The village has a range of housing from apartments to starter homes and larger homes. A shopping center provides a variety of local shopping and a farmers market sets up from May through October. There are a number of eateries from fast food to the acclaimed River Lane Inn. The Village Pond (pictured) offers the charm of the old swimming hole in the summer months, while bike enthusiasts have a number of choices for off-road riding.
 
Year Founded: 1896 (changed from the Village of Prairieville to the Village of Waukesha in 1846)
Population: 70,718
Scouting report: The state's seventh largest city has a vibrant downtown that has been revitalized in recent years. Waukesha also boasts an award-winning parks system and was recently named a Gibson GuitarTown city.