When I first told my family I was going to Lake Geneva, they assumed it was a European tour. But much closer to home for this Canadian is a lakeside oasis by the same name, just as worthy of exploring. In fact, after visiting Lake Geneva in southeastern Wisconsin for the first time recently, I see why it has earned its reputation for being a favorite escape of nearby Chicagoans.
The city is replete with interesting landmarks, unique shops, and award-winning restaurants, but at its heart is the lake itself. As a pristine, spring-fed body of water with a bed of sand, it stretches more than 5,000 acres and reaches depths of more than 140 feet, making it a mecca for water sports, boating, fishing, and swimming.
You can cruise the lake via pontoon, sailboat, and jet ski. Or take a historic US Mailboat Tour with Lake Geneva Cruise Line, as I did, to experience how letters and parcels are delivered to lakeside estates via mail-jumpers leaping off and on the moving vessel.
There are only a handful of places in the US still delivering mail this way. On Lake Geneva, the tradition has lasted a century, with letters and parcels delivered to 75 lakeside residents between June 15th and September 15th. Our mail jumper for this trip, 27-year-old Kyle, has been doing his job for 11 years and has only fallen in the lake three times. Yet our anticipation mounted with every stop as we watched him sprint to a mailbox and then make it back on board in the nick of time.
The cruise itself lasted 2.5 hours and provided a great view of the opulent Gilded Age mansions situated along the waterfront. After the Great Chicago Fire of 1871, wealthy Chicagoans needed a peaceful retreat and found it here. Soon word of the area’s beauty spread, inspiring others to follow suit. Stone Manor, the largest waterfront property with 50 rooms over 20,000 square feet, was originally owned by Otto Young, a German who made his fortune in Chicago real estate and retail. There is also the majestic Wrigley Estate from chewing gum magnate William Wrigley Jr. and the impressive Black Stone Estate built for Chicago Beer Baron Conrad Seipp in 1888.
The stunning homes and their meticulously landscaped yards can be viewed in even more detail by walking the Shore Path around Lake Geneva, which is approximately 21 miles and takes about eight to 10 hours to complete.
Back on land, I enjoyed a delicious lunch at Pier 290, the only waterfront restaurant on Lake Geneva, which has spacious indoor seating and its own sandy beach with firepits. I’m still salivating over the perfectly breaded cheese curds and fresh seafood ceviche.
The antique Apothecary Bar in the Maxwell Mansion turned out to be a lovely spot for an afternoon mocktail, and later that night, I ventured downstairs to a charming speakeasy accessible only by a password available to its Facebook followers (https://www.facebook.com/MaxwellMansion/). (The speakeasy is only open in the evenings from Thursday to Saturday.)
On my second day, I toured the beautifully restored Yerkes Observatory in Williams Bay, which was saved from becoming a hotel and housing development in the early 2000s when residents and officials stepped in to protest. Founded in 1897, it is the birthplace of modern astrophysics in the United States and houses the world’s largest refracting telescope. On top of the astronomy tidbits I gleaned on the tour, I enjoyed learning about the architecture throughout the majestic building and details on the many people from around the world who made their mark in science in this space, including Edwin Hubble of the Hubble Space Telescope and Nancy Grace Roman, who later became NASA’s first Chief of Astronomy and first female executive. For those open to climbing and maneuvering small spaces, there is a Hidden Spaces Tour, which offers a behind-the-scenes look at where astronomers work.
After my starry exploration, I took part in a class through the Lake Geneva School of Cooking. Here, Chef John Bogan was as entertaining as he was skilled in kitchen techniques. After an hour or so of chopping, sautéing, and kitchen comradery, my cooking team and I enjoyed the fruits of our labor: a four-course meal, complete with wine and a mighty impressive-looking vanilla bean crème brûlée.
Another key highlight of my Lake Geneva experience was my stay at the Grand Geneva Resort and Spa. I could have easily spent a few days just exploring this 1,300-acre property, complete with rolling hills and premier golfing facilities. Originally opened in 1968 as one of Hugh Hefner’s first Playboy Club hotels, it features subtle nods to that era with a sunken lounge, pebble-textured walls, and an outdoor pond shaped in the image of the iconic Playboy Bunny. But the space is 100% kid-friendly now with an impressive indoor waterpark and bowling alley at its adjacent Timber Ridge Lodge. It is also renowned for its six-week “Christmas in the County” celebration with private igloo dining, a heated trolley tour of festive lights, and the option for a Christmas tree in your hotel room.
My abode, like most of the 358 guest rooms on site, had a private balcony overlooking the beautifully landscaped property, and sitting out with a coffee each morning was the ideal way to start my day.
I spent my last night sampling the fare at 240 West in The Abbey Resort, recommended for its panoramic harbor views and locally sourced menu. With reclaimed wood beams and a large stone fireplace, the space had a rustic feel while the food was refined—and delicious—with everything from grilled steaks to eggplant ratatouille. The restaurant also features a range of unique cocktails, such as the delightful Maple Bourbon Old Fashioned.
In only a few days at Lake Geneva, I felt like I’d had a true escape. I’m so glad I discovered this Wisconsin haven and am already planning my next trip back.
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