It’s cooler by the lake

Escape to Elkhart Lake, Wisconsin—where vintage racing, fine dining, and lakeside charm await just 90 miles from Milwaukee

Osthoff Resort in Elkhart Lake, Wisconsin / Photo by StellaMc / iStock

Shakespeare famously wrote of “the winter of our discontent” as if he’d foreseen the times we live in. For those of us fatigued by the goings-on of the day, here’s a prescription: escape to Wisconsin’s charming Elkhart Lake, a worth-your-weekend getaway 90 miles westward from Milwaukee.

Chicagoans have been privy to that secret for decades. Folks in the know have spent many a summer in this petite (pop. 900-plus) Wisconsin town, known as a gambler’s nirvana back in the day. Nowadays, visitors swarm here to try their luck at something even racier—racing, to be exact. Since the clean-living Fifties, car (and motorcycle) speed-offs have been the primo draw.

But wait, as they say: there’s more. There are classic lakeside resorts, like the Osthoff, offering everything from relaxing pontoon rides to bonfires on the swimming beaches, plus an indoor pool for year-round paddling.

It’s also home to Aspira Spa, where patrons come in search of soothing services, from massages to pedicures to a stint in its breathe-easy salt room. But now that we’re relaxed, let’s eat!

The Osthoff’s Otto’s offers hearty, quick and casual fare, while Concourse deserves a Michelin star (think lobster bisque and deeply chocolate desserts). And for the DIYers in the crowd, there’s also a cooking school led by Chef Rodney Schulz, who conducts learn-and-dine classes such as ours in pasta-making.

Or grab a burger at nearby Quit Qui Oc, alongside a 27-hole golf course gracing 250 acres of rolling green. (But beware of the mah-jongg ladies, who appear to be playing for blood.) And within the town itself, Lake Street Café holds a few surprises, like a prestigious Wine Spectator award. Owner Lynn Shovan knows what those speed-car fans—including, once upon a time, actor Paul Newman—seek, and that’s her famous tenderloin shiraz to go with the grand reds. Patio seating, too.

Vintage Elkhart Lake, just steps away, can help you discover your palate’s preferences. Pay for a “credit card” to insert in a spout below the selection of your choice, indicate the pour size you prefer, then sip and sample away.

Across the street from the Osthoff stands the recently renovated Siebkens Resort, where accommodations range from fancy condos to more modest Thirties motel-style rooms. Its restaurant, PAM’s, delights diners with everything from ornate salads to plump walleye fillets.

OK: bed and fed, let’s head to the races. In the mid-Fifties, when the local economy needed a boost, a 640-acre venue called Road America was devised to provide the answer. It debuted a four-mile sports-car road course—still virtually unchanged today—where spectators can roam the grounds at will, choosing where they’d like to watch. (Yes, you can even drive it in your own sports car if you ante up. Looks good on your resume, too.)

We, instead, hopped into shiny autos with professional drivers to speed away at 100 mph (BYO oxygen). We then jumped into off-road carts to maneuver across the rolling greensward, through lush forestland and spacious meadows. Many other courses—and classes—also are on offer, such as teaching teens to drive and how to handle winter roads, along with geocaching in go-karts and paintballing. There’s a must-shop gift shop, too.

Oh, you don’t own a sporty race car? I know just the guy who can help you out. Jim Balestrieri, who co-founded Throttlestop, has a few on hand. How about that $600,000 Jaguar? Or the Porsche, a steal at $250,000? Motorcycles, too. “I sold 123 vehicles last year,” Jim reports. “Most of my stock comes from Europe, and people buy it sight-unseen, off the Web. The hardest thing,” he testifies, “is finding new inventory.” Visitors are welcome to strop in and gawk…er, window-shop, he says.

It’s close to All Seasons, another Elkhart Lake classic—but this one serves the kind of eggs-cum-pancakes-cum-sausage diner breakfast that’ll carry you through the rest of the day.

Race cars not your thing? Then head over to Wade House, circa 1850, in nearby Greenbush, Wisconsin, to prowl through the three floors of its stagecoach inn, tap room included. Then explore the Wesley W. Jung Carriage Museum, where you can get up-close and personal with a horse-drawn fire engine, a family-size sleigh, a fancy carriage for the show-offs in town, and a Wells Fargo stagecoach. In fact, its horses are ready, so jump right in and jiggle across the field to the old-time blacksmith shop, where a re-enactor stands ready with a demo, and then on to the water-powered sawmill nearby (ditto).

Finally, gentlemen, start your engines…to head back to Minnesota (or ask Delta to do the same). But wait! It’s illegal to leave Wisconsin without a stop at a cheese shop (well, probably it is), and Henning’s is ready for you. It’s down the road near the town of Kiel, where a fourth generation of cheesemakers has turned sweet local milk into cheeses galore. “At one time, Wisconsin boasted 2,800 cheese factories,” says co-owner Kent Hemming. “All our milk comes from a half-hour away: no mega-farms. We sell 1,200 to 1,500 pounds of cheese. A. Day. And there’s a wide variety of flavor profiles to choose from.” Stroll through the mini-museum, savor a few samples, then load up your shopping bag and head home happy.

For more info and to plan your trip, check out ElkhartLake.com.


Carla Waldemar