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This article created in collaboration with Elkhart Lake.ELKHART LAKE – Elkhart Lake is the best of both worlds: compact enough that it’s easily navigable on foot and bike and everyone seems to know everyone else, but with so much going on and so much to do. You surely need to visit more than once.
That’s why after spending a few days here last summer, I’m back for another round.
One of the things that strikes me most about Elkhart Lake – a little more than an hour’s drive north of Milwaukee – is its small town vibe. When I visited last year, I dined with the owner of The Shore Club, where I stayed. This time, while at Siebkens, owner Wendy Orth stopped at my table for a chat.
When I lunched at Quit Qui Oc Golf Club and Restaurant, both owners were there interacting with customers, many of whom they clearly knew by name.
In fact, pretty much every place I went last year – The Paddock Club, Vintage wine shop, Off The Rail cafe, Throttlestop motor museum, Lake Street Cafe, Switch Gear Brewing – the owners were on-site, engaged, talking to locals. I even encountered restaurant owners dining at neighboring restaurants, supporting the “competition.”
However, even after two visits with tightly packed itineraries, there are places and experiences I haven’t gotten to ... yet.
And here was my visit this time around:
Where to stay
Elkhart Lake has a trio of historic resorts lined up in a row along the north shore of the lake, and I’m slowly making my way through them all.
Last year, I decamped at The Shore Club, founded in 1872 as William Schwartz’s Rustic House, and this time I set up at Siebkens next door, which was also built by Schwartz, in 1883 as the Belleview House. It was purchased by Laura and Herman Siebkens in 1916 and remained in the family until it was purchased by Wendy and Rob Orth in 2019.
The couple already owned a condo at Siebkens, which like its neighbors has privately owned units that are rented as hotel rooms, and when the Siebkens family decided to sell, the Orths wanted to ensure that the historic venue endured.
And it definitely feels historic.
The condo hotel building honors its predecessor on the site with its large balconies, and the Lake Cottage is an 1888 Queen Anne rooming house converted to a handful of guest rooms. There’s also the historic Elm Park Hotel building.
At the center are the old opera house, which now houses an antiques store and the popular Stop-Inn Tavern, which has live music (out on the large patio when weather permits) and food, as well as the main building with the reception and lobby area – where there's free grab-and-go breakfast in the mornings – and P.A.M.’s restaurant.
Of course, Siebkens also has a pool and hot tub, and down a staircase behind the Lake Cottage, a private beach with kayaks, a pier and more.
My favorite little feature at Siebkens are the old stanchions that flank the entrances, boosting the historic vibe of the resort, which is situated in the heart of the original race track course that wound its way through the streets of Elkhart Lake before the construction of Road America about a mile out of town.
Next door is The Osthoff, which is the largest resort in Elkhart Lake and boasts multiple restaurants and watering holes, a spa, an arcade, kids activities, live entertainment – Puddles Pity Party is performing in October! – and more.
The Osthoff has nearly completed the renovation of all its guest rooms and in March recarpeted the entire sprawling place.
There are also inns, B&Bs and other places to bed down in Elkhart Lake and you can find more on those here.
Where to eat
I don’t have stats on this, but anecdotally, Elkhart Lake feels like it has the most restaurants per capita in the state, and there’s everything from diner-style family restaurants to Mexican food trucks to coffee shop/cafes to pizzerias to tavern food to fine dining and more.
For breakfast, check out Otto’s at The Osthoff, which has a new menu that mixes classic options like omelettes and a breakfast sandwich, with avocado toast and other treats. Or head into town for pancakes, breakfast pizzas and more at All Seasons Family Restaurant.
Now under new ownership and with a new name and a new menu is The Garage BBQ Pit, at the entrance to town on Highway 67. You can see and smell the smoker at work as you – and lunchtime – approach. There are sandwiches, wings, chicken tenders, wraps and apps, but come for the barbecue.
Grab a combo plate with burnt ends or brisket or sausages or pulled pork – or more than one – and some sides and expect to carry out your leftovers.
Although I’m not a golfer, I really enjoyed lunch at Quit Qui Oc, an 27-hole course designed in 1923 by Tom Bendelow and reconfigured in 1955, when the Wiese family bought the place.
A third generation of the family still operates the facility and the restaurant – which has a popular Friday fish fry and monthly rib night – is bustling at lunch, serving up burgers, wraps, salads and sandwiches, including a top-flight reuben.
The interior was recently gussied up with a new roof to replace some failing skylights, plus new paint, carpet and more.
You’re likely to see owners Todd and Rachel Montaba while you’re there, and be sure to have them show you the witty little commemorative plaques displayed near the bar.
For dinner, there is no livelier spot, especially on a Wednesday night when there’s live music on tap, than Siebkens The Stop-Inn. Located on the lower level of a historic theater building, it has an almost subterranean speakeasy vibe with some great bar fixtures and breweriana and areas of the walls and ceilings covered in stickers, signs and race flags.
There are apps like maple-glazed carrots and fried shishito peppers, as well as cheese curbs and smoked salmon, plus burgers, sandwiches and salads. For entrees choose an all-day fish fry, risotto and chicken marsala.
I had the Wisconsin carbonara (pictured above), with house-made pasta, SarVecchio cheese and (gasp!) cream, which was at least from America’s Dairyland. It was delicious.
When I visited last summer, Harry’s Pizza e Vino was just launching its soft opening phase, but by now it’s become one of the town’s most popular restaurants.
Al and Laurie Latifi first started doing Roman-style pizza in Sheboygan during the pandemic, but when a space opened up in the heart of Elkhart Lake they shifted operations there and used the same dough to create more traditional round pizzas.
The vibe is dark and warm, the pizzas are incredible, especially the prosciutto and arugula and my favorite, the walnut pizza. There are delicious apps, too, like a bowl of house-made pesto served with a loaf of bread – crunchy and mottled with char spots on the outside, pillowy soft on the inside – made from the pizza dough.
There’s an extensive wine list and some house-special cocktails like The Kink with bourbon, housemade sweet and sour mix, a cabernet wine float and a lemon twist.
Grab a Nutella pizza for dessert and don’t miss out on the housemade nocino (made from locally grown English walnuts) and limoncello. You can see them both steeping in large glass jars in the dining room.
If the beautiful bar and back bar look familiar, it’s because they were purchased from Flannery’s in Milwaukee, which closed in early 2023.
If you want a traditional dessert in a classic ice cream parlor setting, hit up Gessert’s Ice Cream & Confectionery, which opened in 1922. The place retains its 1920s vibe and look and has a wide range of candies and ice cream and even counter seating at the soda fountain.
What to do
Because temps were hovering around 103 degrees when I visited in 2023, I didn’t get to do much hiking, so I was sure to include a bit of that in this year’s itinerary.
I walked two sections of the Ice Age Trail LaBudde Creek Segment, which are a short drive – or bike ride (you can rent bikes at The Osthoff) – from town. These two trails – which are, sadly, not contiguous – wend their way through the Kettle Moraine’s LaBudde Creek wetlands area for a total of 3.35 miles, and each offers a different feel.
The southern segment is forested, with occasional breaks, while the northern section is mostly open prairie. Both were empty and therefore perfectly quiet when I hiked midday, mid-week.
While I was in town, a few folks mentioned the Old Plank Road Trail, which runs more than 20 miles from Sheboygan out to Greenbush and is being extended. Next time I get back I’m hoping to check out that one, as well as the Broughton Sheboygan Marsh Park, which has an observation tower.
I spent my days running, taking a late afternoon cruise on a pontoon boat from The Osthoff’s watersports cabana and kayaking with a rental from the same place. Later, I enjoyed the chairs out at the end of the Siebkens beach dock; a little evening serenity perched on a dock jutting out into a Wisconsin lake is highly underrated.
At night, I enjoyed free live music at The Stop-Inn (inside, due to the rain) and lakeside the following night at The Osthoff. I plan to head back to the latter this autumn to check out Puddles Pity Party, who performs on Oct. 26 (that show requires tickets).
Last year, I had hoped to take advantage of Road America’s 4 Miles of Fitness, which allows runners, walkers and cyclists to utilize the four-mile race track from 6 to 8 p.m. on Mondays and Wednesdays, but the blazing temps put an end to that.
This time, my hopes were dashed by thunderstorms and downpours, but fortunately, the folks at America’s National Park of Speed aren’t afraid of a little water. So – thunderstorms not yet arrived, but rain bucketing down – Programs Coordinator Troy Matenaer handed me a poncho and we hopped into some Yamaha off-road vehicles to splatter some serious muddy water as we scaled rocky hills, tracked through deeply rutted dirt roads and bonked over boulders.
It was thrilling and especially so because of the rain and mud, leading me to decide that the only way to properly off-road is to do it in a downpour.
Next, we rode over to the go-kart track and did a few laps on karts there, more hydroplaning across the blacktop than actually driving. Again, thrilling and exhilarating and a reminder that Road America is more than a place to be a racing spectator.
In addition to being one of America’s top racing venues, RA is also a place for team building, group outings and individual fun doing things like geocaching, motorcycling training, go-karting, off-roading and more.
Hopefully next time Mother Nature will finally let me run the four-mile circuit.
After all that jostling, hiking, kayaking and running, a visit to the Aspira Spa at The Osthoff was a welcome change.
After spending nearly an hour in the salt room with its soothing yellow hue, quietude and relaxing chaise lounges – where, as promised, I fell asleep – I got an 80-minute Sacred Waters Hydrating Massage, which was a full-body deep tissue massage with the added benefit of “sacred native pouches, (that) hold the healing crystal-clear Elkhart Lake water.”
These are “placed on the body’s energy centers to restore a grounding flow of energy to the chakra system.”
I’m not sure I know what it means, but I’ll tell you it definitely works to soothe sore muscles and relieve pent-up tension.
The spa was a pitch perfect way to say goodbye to Elkhart Lake – for now – and as I pointed the car out of town, only one thing was missing ... cheese!
So, I detoured over to nearby Kiel and spent an hour at Henning’s Cheese with third-generation cheesemaker Kert Henning as we discussed cheesemaking, the cheese business, the fourth generation of Hennings that are involved in the business and more.
After checking out the museum of cheesemaking equipment and watching cheese being made through the viewing windows, I grabbed some examples to take home – truffle cheese, 11-year-old cheddar and bourbon-infused cheese.
I left the Elkhart Lake area having eaten well, relaxed, enjoyed a ton of fun and resolved to get back to this biggest of small towns as soon as possible.
Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.
He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.
With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.
He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.
In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.
He has be heard on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories, in that station's most popular podcast.
