From Railroad Travelers To Road Racers, The Historic Osthoff Resort Attracts Vacationers and Jet Setters

The year is 1886. More than two decades have passed since the last shot was fired in the Civil War and Grover Cleveland is serving what will be the first of two presidential terms-and also become the first president to marry while in office. Coca-Cola is created and the St. Louis Browns defeat the Chicago White Stockings in the World Series.

America is enjoying the prosperity of the “Gilded Age” as fashionable travelers pack steamer trunks and seek respite from the summer dust and heat of the city. Many head for the exciting new Osthoff Hotel in Elkhart Lake in southeastern Wisconsin, opened in 1886 by German entrepreneur Otto Osthoff and his wife Paulina. Quickly, The Osthoff becomes a favorite of affluent travelers who appreciate luxurious accommodations and an ambiance featuring quality entertainment and fine dining.

City folk from Chicago, St. Louis and Milwaukee are taken with the idea of traveling north by rail for a summer holiday. More than 2,000 visitors weekly are pouring into the tiny village of Elkhart Lake in pursuit of a place beside the fresh, spring-fed lake (that, more than a century later, still is valued for its water quality). By the dawn of the 20th Century, six resorts have emerged in or around Elkhart Lake. The boom continues well into the 1900’s, fueled by the inauguration, in 1909, of Interurban service into the village.

In the next 90-plus years, the tiny resort community and with it, The Osthoff, is to experience a rich and colorful history. The town becomes a gambling haven and a Prohibition-era hideaway for gangsters, where speakeasies coexist with dairy farms and revenue men track moonshiners. In the mid-1950s the Osthoff Hotel is sold and for more than 30 years is operated as a drama and arts camp.

Fast-forward to 1989, with The Osthoff ready for its next incarnation. A group of investors purchase the property to develop a condominium resort. They recognize that the setting is ideal, with acres of wooded grounds and 500 feet of sandy beach fronting what remains among the purest lakes in Wisconsin. Capturing the grandeur of the original Osthoff Hotel, today’s resort opened its doors in 1995 and offers all-suite accommodations and four seasons of recreation, from sailing to ice skating as well as stunning scenery and an unmistakable Old World charm. It quickly earned the prestigious AAA Four Diamond rating, making it one of the premier resort destinations in the Midwest. In 2002, the Wisconsin Innkeepers Association presented The Osthoff Resort’s general manager with its coveted “Innkeeper of the Year” award. With the completion of a major expansion in 2005, The Osthoff Resort has added a massive new wing featuring a 10,000-square-foot conference center, 100-seat restaurant, destination spa and 48 additional two- and three-bedroom suites featuring both lake and woodland views.

Special events, from a re-creation of a traditional German Christmas market on the Osthoff grounds to the nationally acclaimed “Jazz on the Vine” music and wine festival, draw visitors year-round. And while the old train depot still stands in the center of Elkhart Lake more than 100 years later, you’ll find most visitors today arriving at The Osthoff Resort by car.

Early History of Elkhart Lake

The Potowotomi Indians first called Elkhart Lake “Me-shay-way-o-deh-ni-bis” (or Great Heart Lake) after its shape resembling an elk’s heart. Scooped out by the ancient glaciers, the lake is wrapped by the lush woods of Wisconsin’s beautiful Kettle Moraine. Early settlers from the Rhine region of Germany were attracted to the area for its farming potential. Soon after, visitors came by stagecoach, then train, drawn to the lake, the charming resorts around its shores and to the abundance of recreation.

In the early 1950’s, the arrival of motor racing breathed new life into the region, attracting elitist road racers with their exotic BMWs and Porsches. In the beginning, gentlemen race-car drivers actually held their races on the streets of the village and county roads. These were soon discontinued because of problems with crowd and traffic control, and Elkhart Lake became home of the Road America road-racing circuit. This permanent track was built into 570 acres of rolling hills southeast of the village and became the longest natural road racing track in North America. Soon, the village regained its old luster as it became a major stop on the international auto-racing circuit, spoken of by racing glitterati in the same breath as Monte Carlo.

In all, the permanent population of Elkhart Lake is just over 1,000 residents. Nearly everything is within walking distance, from landmark resorts to newer galleries and boutiques, giving it added charm. Regardless of season, weekends always bring vacationers strolling the streets. The appeal, it appears, is indeed timeless.