Sip, savour, and explore Lake Geneva — a hidden gem of the Midwest

ABOVE: Visit Maxwell Mansion for amazing drinks at their speakeasy, and stay for the Great Gatsby vibes!

Situated between Chicago and Milwaukee is one of the most phenomenal vacation resort towns in the United States. Lake Geneva, Wisconsin, is where unique food culture and friendliness meet with the old money of Chicago, mixed with a history that is as old as the state itself.

To start, not many can say they’ve stayed in the Playboy mansion. Kitschy or not, it’s a cultural institution. The Grand Geneva Resort and Spa opened as the first Playboy Club Hotel in 1968, with a storied, if not seedy, past that the resort’s well-written history book covers in great detail. After becoming a family resort in the 1980s, the resort was purchased by Polish Immigrant Ben Marcus who renovated and reinvigorated the property turning it into a luxury hotel with incredible suites on 1300 acres of country beauty.

ABOVE: Once a Playboy hotel, The Grand Geneva Resort is a luxurious escape close to all the attractions of Lake Geneva. (Photo: Courtesy Travel Wisconsin) 

The multi-award-winning resort boasts two internationally acclaimed golf courses, a sports centre with a rock-climbing wall, a ski hill, and a waterpark. The resort also has multiple indoor and outdoor pools to relax in. The Grand Geneva feels like being in a New England Country club and is truly luxurious.

For something with a little bit more history, Lake Lawn Resort, which dates back to 1878, is another great spot about 20 minutes outside of Lake Geneva on the beautiful Lake Delavan. The resort is famous as the place of the invention of the Pink Lemonade. The Lookout Bar & Eatery is a fantastic place to grab lunch or breakfast and enjoy the views of Wisconsin’s natural beauty. The restaurant’s executive chefs’ talent is incredible, going as far as to tap trees for the maple syrup he uses on bacon and making his own pickled preserves for dishes.

The municipality of Lake Geneva is a short 10-minute drive from the Grand Geneva and 20 minutes from the Lake Lawn Resort. Being the playground of the Chicago elite of the late 19th and early 20th centuries, the mansions on the shore of the lake are a worthy site to see.

 ABOVE: The Stone Manor is the largest Mansion On Lake Geneva, in a town known for its giant lakefront mansions. 

Follow the nearly 21 miles long walking trail around the lake and take in the grand summer homes, living artifacts of old American money. If cruising is more your style, Lake Geneva Cruise Line offers a guided historical tour of the lake on their ship, the Walworth. The two- and half-hour trip is a great way to learn about all the mansions lining the shore and their history. Even if history isn’t your forte, the journey is entertaining due in part to the ship’s mailman.

ABOVE: The ambitious mail run from a moving boat to box and back is performed by brave young people!

Part sightseeing cruise, part mail delivery service, from June to September each year, one incredibly fit mail delivery person continuously jumps off the boat, runs to a mailbox, deposits the mail, and returns to the ship. The cardio and stamina required to do the job is not for the faint of heart; the Walworth makes 75 mail deliveries a day.

Around the same time Lake Geneva became a playground of the Midwest elite, it was also at the cutting edge of science and technology. From the mailboat tour, you’ll pass an Edwardian-looking building called Yerkes Observatory; it is a must-see.

Opened in 1897 as a satellite site of the university of Chicago, the building is currently undergoing restoration. However, the refracting telescope housed within the building, the largest in the world for over a decade, is still in use today. Dr. Amanda Bauer is the site's chief academic, and her wonderful, guided tour shows the true marvel of the design, which includes a floor that raises or lowers so that astronomers can look through the behemoth device.

ABOVE: The mechanical telescope at Yerkes Observatory, the first to capture photos of the planets, was such a wonder at the time of its building that Albert Einsteins' only desire when visiting America aside from visiting Niagra Falls was to see the telescope.

The first close-up photos ever taken of the planets were thanks to the Yerkes Observatory, and some of the original negatives are displayed on-site. So impressive is the telescope that on his first trip to North America, Einstein wished only to visit two sites, Niagara Falls and the Yerkes Observatory.

The Yerkes Future Foundation runs the observatory and hopes, once the restorations are completed, the facility will be used for both research and public outreach. Yerkes also boasts an impressive collection of scientific books and papers dating back to the enlightenment era, enthralling for the history-obsessed or science lover.

ABOVE: Make sure to take the mailboat tour with Lake Geneva Cruise lines!

Lake Geneva is a paradise for foodies with farm-fresh produce, cheeses, and meat mixed with complex cuisine. In the town, you’ll find what Wisconsin is known for: cheese, local wineries and breweries, swanky but unpretentious cocktail lounges, and restaurants that easily stack up against well-known establishments in Toronto or New York.

The Geneva ChopHouse warrants the drive out to the idyllic Grand Geneva Resort. The restaurant crafts some of the most gourmet and flavourful appetizers imaginable, including Potato Pave, White Truffle and Miyazaki beef Tartare paired with recommended wines by the steakhouse’s resident sommelier Andy Kulakowski. The ChopHouse’s beef is world-class, and their Porterhouse Steak and Argentinian Pichana are hand-selected. The quality of the meat is astounding; treating yourself is entirely justified.

Einstein wished only to visit two sites, Niagara Falls and the Yerkes Observatory, on his first trip to North America

ABOVE: The Delicious goat cheese at Sopra on Main Street.

More centrally located on Main Street, Sopra is a wonderful option for the gourmet. This restaurant describes itself as an Italian-American bistro. Still, its food is complex yet comfortable all at the same time. Owned by Alastair Cumming and his son Simon, who is also the head chef, the restaurant doesn’t shy away from using international inspiration.

The senior Cumming fondly described international tasting expeditions with his son to find inspiration for their menu. The warm Caesar salad served with grilled stocks dressed with the freshest ingredients, including a wonderfully sharp parmesan, was a flavour explosion that perfectly contrasted each element’s best attributes. The breaded goat cheese and pickled beets were also a testimony to the quality of the fresh foods. The pasta dishes at the restaurant were gourmet, ranging from linguine Bolognese to squid ink seafood pasta. Trying the trout and pesto gnocchi was a particularly memorable culinary experience, as the local freshwater fish paired exceptionally well with the Italian-inspired pesto and sundried tomatoes.

Another establishment with an excellent reputation among the locals is Pier 290. Owned and operated by Bill Gage, who also owns Lake Geneva Cruise Line. Gage created a seafood restaurant that provides an ideal atmosphere through the usage of refurbished and antique nautical and naval décor—a point of pride his larger-than-life personality happily points out.

The food at Pier 290 is fantastic; the lobster roll is particularly delicious, and the blackened tuna sandwich is also excellent. The vibe and the energy of the restaurant are fantastic. Sitting on the patio looking out at the lake, it is hard to believe that you’re not at a seaside New England restaurant, that is, until you have some of the fried cheese curds. Sorry Canada, but Wisconsin does them better.

ABOVE: Hill Valley Cheese Shop and Bar is a great place to go for a tasting and drink, making some of the best cheese in Wisconsin!

Another great spot is Oakfire Pizza, a Neapolitan pizza joint located along the beach near the boat tour launch. It is a good option if you want to enjoy a casual lunch on a break from the beach or after the mailboat tour. The pizzas are traditional Italian style, and their buffalo mozzarella margarita hit the spot.

On the subject of cheese, located just a couple of hundred metres from Lake Geneva's Main Street is one of the best social atmospheres for wine and cheese lovers. Hill Valley Dairy offers fantastic cheese boards at their bar, made from fresh, locally sourced milk. The cheese is a passion project of owner Josie Henningfeld and her husband, Ron. Everything, from their cheese curds to their gouda and black pepper cheddar, is fantastic.

Ron Henningfeld, the principal cheese maker, grew up on a dairy farm and has a lifetime of experience and passion for making tasty cheese. Not only will Hill Valley Dairy make you an amazing cheeseboard, but they can also pair it with nuts, bread, and meats like bourbon-marinated flank steak, and make great wine and drink recommendations for pairing.

ABOVE: The Ulysses S. Grant room at the Maxwell Mansion.

If you crave a beer over a cocktail because you’ve had a lot of Wisconsin cheese, there are some other great options in and around downtown. Maxwell Mansion, located about 1 km from Sopra, is the perfect spot for an after-dinner drink. The mansion is the passion project of the Piefiers, the latest owners of lake Geneva’s oldest mansion. Used as a guest house for decades, its American 1860s to turn-of-the-century style is absolutely stunning.

Famous guests include legendary US Civil War General and later President Ulysses S. Grant. His former suite can serve as your accommodation. The Maxwell mansion also hosts a swanky upstairs bar serving great mixed drinks like their hibiscus gin & tonic, a cocktail so smooth you may forget there is alcohol in it. Even better is the speakeasy in the basement that requires a password to enter, like the real deal — mansion guests are given the password while locals have their ways of finding it out.

ABOVE: Topsy Turvey Brewery is built in an old church and makes some of the tastiest craft beers in town. Their German-style Marzen beer was fantastic!

Sometimes you want to sit on the patio and have a beer, and Lake Geneva has some pretty great craft beer. Topsy Turvy Brewery is a funky craft beer spot located in an old church in the centre of town. The bar is made up of Jenga blocks, but don’t think you’ll collapse in disappointment — In an age where craft beer is synonymous with IPAs, Topsy Turvey has something for everyone, and it’s all delicious. European beer fans will love their German Marzen-style lager. They also have Stouts, Mexican lagers, Hazy IPAs, and Wheat beers.

ABOVE: We tasted bourbon-barrel-aged port at Staller Estate Winery. It ?is rich, chocolaty and fantastic!

Just outside of Lake Geneva, there are also some fantastic wineries. While California wines are among the best-known exported US wines, Wisconsin’s got some young but promising competition. The Stallers, a husband and wife team with a background in science, run Staller Estate Winery. Located about 20 minutes outside of town, Staller Estate offers up wonderful red and white wines, but their port aged in bourbon barrels with notes of chocolate can convert even those most skeptical of fortified wine. Wendy Staller proudly displayed the copper still used to make the brandy they put into their ports.

ABOVE: Judy Jacobson of Apple Orchard and Winery with apples from their 4,000-tree orchard. 

Wisconsin, like Canada, is known for its autumn season and the variety of tastes accompanying the fall harvest. The Apple Barn Orchard and Winery is a great place to look if you want to grab some fresh apples, try some tasty kid-friendly cider, or taste some adult-friendly wines made from seasonal fruits like pear or blackberries. The Apple Barn Orchard and Winery has a very wholesome feel that you must experience.

After a day of indulging, head to the Hunt Club Steakhouse for a fantastic meal. The restaurant has an excellent wine list that won’t disappoint in an elegant atmosphere that’s not too uptight. The steaks are fantastic, with the fillet mignon being particularly popular. Their non-beef options were also great. The Tomahawk Pork Chop was a juicy, flavourful culinary delight served with incredibly succulent sides like the restaurant’s amazing Brussels sprouts.

End the night by seeing a show at the Tristan Crist Magic Theatre. Named after an award-winning local magician, Crist’s tricks go as far as having a helicopter appear on stage, making a Harley Davidson motorcycle teleport, or his assistant disappear in the blink of an eye. Crist also shares the stage with magician Brett Daniels, who uses a group of parrots he has owned for over 30 years in his act, taking card tricks and magic feats to the next level. Crist’s show is intense and entertaining and will leave you amazed at how he did it.

Lake Geneva is a beautiful place with some of the most interesting historical sites, entertaining shows, and the best food and drink options anywhere in the mid-western United States. The friendly ways of Wisconsinites, who seem more like Canadians, remind you that you’re not that far from Ontario or central Canada. If you have a layover in Chicago or want a summer destination that’s not Florida, the Carolinas, or Virginia Beach, then consider Lake Geneva. You won’t regret it, but with all the delicious wine and food you eat, your waistline might!

Lake Geneva is a destination Canadians should consider.

Photos: Mckenzie Donovan