Oconomowoc: 39 lakes within half-hour drive

I’ve driven the 77 miles between Madison and Milwaukee at least a couple of hundred times, usually while preoccupied and rarely at a leisurely speed.

So it’s been easy to ignore Oconomowoc, one of the state’s few five-syllable cities and probably the only one with five Os. In the shadow of Wisconsin’s two largest metro areas, this burg off of Interstate 94 has been overlooked as the urban growth of others has sprawled.

That’s a shame, and that’s about to change.

A large part is due to the city’s largest development ever, about 1,500 acres held by the Frederick Pabst family since 1906. At I-94 and near Highway 67, this farmland is being turned into retail boutiques, a business park, about 900 homes, and more.

It has been a bit controversial, with green space preservation, big-box retailers and a strategic zoning change all fodder for debate. What’s apparent is that Pabst Farms represents a significant part of Oconomowoc’s future.

But drive downtown – toward Lac La Belle and Fowler Lake – and it’s clear how the lavishness of the past has molded the city’s personality and pride.

La Belle and Fowler are two of 39 lakes within a half hour’s drive. These waters have been both popular fishing holes and picturesque scenery.

The city historically has attracted the wealthy, first as a resort area, then with the development of huge summer homes. Retail magnate Montgomery Ward and meatpacker Phillip Armour are among those who used to live here. It’s been a playground for beer barons and bootleggers, gangsters and millionaires.

“Newport of the West” is what Oconomowoc was called during a prosperous era that began in the 1870s and lasted until the 1930s. Draper Hall, an imposing hotel, had presidents Taft, Grant, Cleveland, Coolidge, McKinley and Teddy Roosevelt as its guests before being razed in 1967.

One of the stately Victorian mansions, built in 1879, has been turned into an exquisite, 19-room bed and breakfast. Named the Inn at Pine Terrace, it is on the National Register for Historic Places.

The city is small enough to get excited about its high school homecoming weekend. Downtown merchants let students decorate their storefronts; locals lug lawn chairs to the parade route, clogging traffic and sidewalks on a warm but windy October day.

In summer, it is the beach – and the music from the American Legion Band in the downtown band shell – that will attract a crowd.

The city is large enough to lure an eclectic range of talented artists to its downtown galleries. These include Andrew Goralski, whose specialty is portraits of pro athletes and whose customers have included Walter Payton, John Elway and Brett Favre. Goralski also has been on a mission to restore old photos of city life.

The city also is large enough to count the plush, 256-room Olympia Resort and Conference Center as its own. The Olympia’s outdoor facilities include an 18-hole golf course (one of three in the city) and downhill skiing on the Highlands, a manmade hill that is 235 feet high. Snow also has been manmade this winter.

Large enough to have a train depot, but not to have a train stop at it, the Oconomowoc depot was turned into a restaurant.

Ten years ago, the city gave its armory to local historical society. So now it’s the Oconomowoc and Lake Country Museum, a thoughtful compilation of local history that includes an impressive “Streets of Old” gallery that is similar to the Milwaukee Public Museum’s “Streets of Old Milwaukee” exhibit.

There are artifacts from a Victorian home, dentist’s office, barbershop, print shop, general store, medical clinic, railroad and old-time classroom.

Since just under 100 millionaires had lakefront estates here at one time, during warm weather there are guided walking tours around Fowler Lake. Mail boat tours of Lac La Belle also can be arranged.

Way back in 1837, the Indians named this city Coo-No-Mo-Wauk, which means “where the waters meet.” For more about Oconomowoc, go to www.oconomowoc.org or call (800) 524-3744.

The big winter event for Oconomowoc is its annual Chill Fest, a winter carnival that will be Jan. 31 and Feb. 1 – with or without a natural blanket of snow. For the first time, activity will include Mid America Extreme Races, in which 300 people will compete in a six-hour test of skill and endurance. The contest involves trail running, cross country skiing on and off of trails, biking, snow tubing and snowshoeing.

For the less hard-core athlete, there will be winter volleyball and softball, trick skiing contests and snow golf. For all, there will be music, food, a parade and fireworks.

The 8 p.m. Snow Ball dance is the only Jan. 31 event. Other events will be throughout the day and night on Feb. 1. Activities are at the Highlands at Olympia Resort.

For more about the Extreme Races, go to www.adventureracing.net/newmax/races/frostyfrog/frostyfrogframe.html.

It’s unusual for cities of 13,000 to organize media familiarization tours, and it’s unusual for me to accept an invitation. I typically prefer to be anonymous when in search of odd attractions, quaint shops, character(s), diners and elegance in rural and urban areas.

But you should know that is how I met Oconomowoc, and it was a pleasant deviation from the interstate. I had a lot to learn, and my teachers were gracious. As a token of appreciation to them and their efforts, a donation has been sent to further the work of the nonprofit Oconomowoc Historical Society.