Play Around Town in Middleton

Big city amenities and small-town charm coexist in the Good Neighbor City

At first glance, it may appear that Middleton is just another ‘burb living in Madison’s shadow. But look closer and you’ll see the “Good Neighbor City” is home to its own unique history—the remnants of which can be felt today.

It was a railroad stop—appropriately named Middleton Station—that started it all. Opened in 1856 and initially a stop for those traveling from Madison to the Mississippi River’s shipping lines, businesses seized the opportunity to be located nearby. And while no longer in operation, these entrepreneurial legends—from a grain elevator and a pickle factory to an opera house and a blacksmith—live on in the historic edifices that now house new businesses and the registered historical sites that remain in between.

Boasting parks, conservancy areas and a selection of charming shops, restaurants and bakeries that draw downtown dwellers west, there are plenty of unique places to land in Middleton. And thanks to a family-friendly vibe, Middleton hit the national map when Money Magazine ranked it the “Best Place to Live” in 2007.

While the city has come a long way from its iron-horse heyday, you can be sure that there is a strong sense of pride in its humble beginnings—and that the good neighbor spirit of yesterday lives on today. —Lauren Kiesow