Wauwatosa
vs.
Waukesha
 
Year Founded: 1892
Population: 46,396
Scouting report: Wauwatosa's Village and East Tosa districts offer an eclectic array of small shops and eateries. It is home to Mayfair, the mall that draws stores found nowhere else in Wisconsin. There's plenty of outdoor recreation: splash in the Tosa Pool at Hoyt Park, walk among butterflies at the Monarch Trail, bike the Oak Leaf Trail or Menomonee River Parkway or play at the newly developed Hartung and Hart city parks.
 
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.