Retreat to Racing Town

Elkhart Lake Beckons Holiday Travelers 

written by JENNIFER COLOSIMO | photography courtesy of JENNIFER COLOSIMO; THE OSTHOFF RESORT; ROAD AMERICA


December, for many of us in the South, means long shopping lines and hours manning a sugar-cookie-filled oven. For a small part of the population in Wisconsin, it is one of the most anticipated times of the year for trudging through snow, sipping hot cocoa and sampling fare from across the pond.

The latter happens this month on Elkhart Lake, Wis. at the historic Osthoff Resort. Hundreds of vendors touting authentic, handmade goods set up shop for the annual Christmas Village. Hundreds upon hundreds of shoppers, vacationers and local fans flock to the great hall and stock up on fresh sausages, hand-blown glass ornaments, rich textiles and more. It’s a tradition meant for generations to enjoy – and one that nests perfectly into a town’s tradition for a vacation well spent.

A direct flight from Atlanta to Milwaukee and an easy hour’s drive north puts you into the tiny town of railway crossings, vintage shops and Road America, one of the most famous raceways in the nation. At Elkhart Lake, perhaps Wisconsin’s best-kept secret, some of the state’s top cuisine can be found on menus featuring everything from award-winning wine, Midwestern spins on barbecue and order-at-the-counter sandwiches. It’s a retreat from the hustle and bustle of your stereotypical resort and city destinations.

Stuff Your Face

No, it’s not a very big town, and it doesn’t have anything to offer on the commercial side of things — unless you count a Subway that locals rarely mention. What it does boast is a handful of top-notch restaurants that have put as much care into curating their menus as they did their unique atmosphere. My very first meal at Lola’s on the Lake proved that albeit a short trip, I wasn’t going to leave hungry. Lola’s rests on the lakeside front of The Osthoff Resort. It’s named after the general manager herself, and the same pride she carries for the resort seeps into both the menu and the restaurant’s service. If you only have one meal here, I suggest you try the Wisconsin Cheese Plate (it’s changed my go-to cheese choice), someone at your table share their scallops and then you split the Belgian Dark Chocolate Mousse Framboise — it’s as decadent as it sounds.

Less than a mile away — walkable, if you’re ok with a little snow and a lot of cute architectural sightseeing — Lake Street Café welcomes diners into an easy dinner choice. On one side, you’ve got billiards, a bar and high-top tables perfect for enjoying a wood-fired pizza and something on draft. Through the hall, white linen tablecloths beckon sippers to peruse a Wine Spectator award-winning list gathered from around the country featuring more than 200 vinos ready to open, pour, swirl and enjoy alongside your Shiitake Chicken or Orecchiette Con Carne.

If you doubted that the city encourages pedestrian activity, check yourself, because there are way too many calories to consume on its few streets for someone not to walk them off. My indulgent favorites were the center-oftown Off the Rail parked at the crossroads and sporting a walk-up counter of chalkboard menu paninis, soups, cold sandwiches and baked goods. The tiny little restaurant smells heavenly, making the options difficult to choose between, but the Freight Train, a piled high portion of turkey, Havarti, bacon, sprouts and sourdough, was a wise decision. Around the corner, The Black Pig celebrates all things pork. Their signature Pork and Beef Chili is a perfect way to warm up amidst Midwest weather, but save room for the Berkshire Pork Egg Rolls and big bowls of Mac Attack macaroni and cheese. This Southern-inspired craft kitchen sits on top of what used to be the restaurant’s holding pen on busy nights — now a renovated bar and tribute to all things Road America.

Get Your Thrills

Perhaps it’s more than appropriate that much of the town nods to the pastime because you can’t mention Elkhart Lake without noting the racing craze that put this destination on the map, as a dot or not. In the 1920s and 30s, spectators would line the streets to watch drivers whip around corners and accelerate down the straightaways. In a town known for vacationing mobsters as well as well-to-do families, the reasons to game and gamble were numerous — the racing fit right in. For obvious reasons — namely standing on a street corner counting on the fact that a car’s brakes will work — the city decided to build an official raceway where the sport could be enjoyed safely and extensively, all year long. Now, Road America is one of the world’s fastest permanent road racing tracks, bringing multiple types of racing to the city, not to mention a few celebrity drivers and a ton of other park adventures.

Besides the racing, seasonal vacationers are also drawn to numerous options for dining and relaxing, making Elkhart Lake quite a busy place when laps are completed. That’s where the magic of a small town’s charm begins, bringing visitors back year after year, often across several generations. The 4-mile lake glistens with water skiers, sunbathers, tubers and fishermen during the warm months,but once winter hits, The Osthoff Resort opens its onsite pond for ice-skating, sleds and snowshoes.

See and Shop Till You Drop

When temperatures drop, indoor itineraries abound. Owned by Pat Robison, Two Fish Gallery is decorated wall to wall with local and free trade artisan works and offers weekly art lessons in the workshop. Year-round entertainment produced by Victorian Village Theatre not to mention Aspira Spa’s treatment menu, which could keep you occupied (and relaxed) for an entire vacation, are two more agenda-filling options popular with locals and tourists alike. For those brave enough to weather the cold, outside activities include ecology tours, biking and hiking trails that span the lake and, if your mind (and wallet) is still on shopping, then your cold-weather temptations have just begun.

The annual Old World Christmas Market kicks off the holiday season this month with vendors showcasing handmade goods, tasty treats, jewelry and more. But it’s not your average crafts show — these vendors are the real deal, with handmade goods that have made the trip overseas for hundreds of years. For 10 days, snow-dusted shoppers can immerse themselves in classic culture and take home a suitcase more than they came with while the kids can have breakfast with Santa, peek at the reindeer and participate in their own packed calendar of holiday-inspired activities. That is, of course, if they’re on the nice list.

My own wish list includes another stay at The Osthoff Resort, a packing slip from Vintage Elkhart Lake (the town’s go-to wine, cheese and olive oil shop that will ship goodies that won’t fit in your carry-on), pottery classes and a day trip to visit the surrounding land’s historical treasures such as Henschel’s Indian Museum, a must-see stop where kids can search the grounds for still-buried arrowheads and more.

For me, a zip code packed with Old-World culture came alive as a place for new discovery and endless adventure, topped off with a serene stay on a white-capped lake. It may be smack in the middle of nowhere, but it’s the somewhere I want to be the next time the South skips their snow season. elkhartlake.com