ELKHART LAKE – Visiting Elkhart Lake each summer has become something of a tradition for me in recent years, as I’ve experienced this awesome getaway – just about an hour from Milwaukee – for three years in a row now.
After enjoying much of what this classic Wisconsin lake resort town has to offer – incredible dining, a variety of accommodations, a vast array of activities and more – on my own, this year I wanted to share it with my kid before the new school year kicked off.
You can check out my Elkhart Lake fun in the past couple years in this One Tank Getaway article and this follow-up.
For this special trip, I mixed some new experiences and introduced my kid to some things I enjoyed on previous visits. Having the time together before another extended period apart felt extra special.
Elkhart Lake (the body of water) is one of the deepest lakes in the state – albeit one that’s not too big and noisy (every day is a no-wake boating day until 10 a.m. and on Sunday, that calm lasts all day long) – and floats resorts, plus a public beach and boat launch, too, so it can be enjoyed by all.
And, it’s all part of a compact and walkable small Wisconsin town that’s full of charm, a stone’s skip from outdoor activities, small towns and other attractions.
But perhaps the best part of Elkhart Lake is that it’s a year-round destination. Although I haven’t visited (yet) in winter, most of the activities and experiences I’ve had are suitable for spring, summer and autumn ... and many in the colder months, too.
Coming back this fall is Elktoberfest. The fourth installment of this annual festival takes place on Sept. 20 and includes a farmers market, a fun run/walk, kids’ activities, games (pumpkin bowling!), live music, a root biergarten, a stein social and more!
Find all the details here.
For a broader guide to Elkhart Lake, check out this article.
Where to Stay
While the neighboring Siebkens and The Shore Club have long histories rich in Prohibition-era gangsters, gambling and bootlegging, The Osthoff Resort is younger.
A much larger and more modern accommodation, The Osthoff, however, also has an interesting history and deep roots in Elkhart Lake.
German immigrants Otto and Paulina Osthoff opened Ostoff’s Hotel (after briefly calling it Hotel Muesterand) on the lakeshore in 1886 and it was expanded over the years to include a pavilion and, later, an Art Deco bar.
In 1955, the Osthoff family sold the property of Chicago’s Sulie and Pearl Harand, who converted the resort into the Harand Camp of the Theatre Arts, attended by the likes of singer Lissie, Sen. Russ Feingold, writers Laura Lippman and Jessica Poter, and actors Jeremy Piven, Billy Zane and Virginia Madsen.
The camp closed in 1989 and was sold to Dairyland Investment Company, which replaced the old buildings with the resort you see today.
The Osthoff Resort – which opened in 1995 – has the most modern facilities of the town’s resorts and they’re only getting more modern, with room renovations continuing apace now that new carpeting and other aspects of the public spaces have been completed.
The rooms are suites with kitchens and balconies and there is a full-service spa; one indoor and two outdoor pools; a sauna; a beach; a fitness center; an arcade; a kids programming suite; multiple dining options; free parking; docks; watersports rentals, including kayaks, lake cruises and more; an outdoor bar with live music; and the grounds are beautifully landscaped.
Because there is copious event space, The Osthoff is often alive not only with family vacationers but with meetings, conferences, weddings and other events. Consequently, the entire place thrums with the vibes you’d expect from a Wisconsin lake resort.
We especially enjoyed the balcony overlooking the landscaping and the lake and spent a couple nice summer evenings out there watching movies.
Where to Eat
For breakfast, consider All Seasons Family Restaurant (510 E. Rhine St.), which is a classic diner-style breakfast and lunch spot with a menu of hearty favorites, and counter seating if you want to socialize and booths and tables if you want a little more alone time.
The omelets here are especially good and the hash browns especially crispy. The food isn't fancy and neither is the setting, but both are down-home solid and hit the spot.
Also great for breakfast and lunch (except on Wednesdays, when it’s closed) is Off the Rail (44 Gottfried St.) located in the heart of downtown in an 1871 trackside train depot later converted into a feed mill.
Here there are great sandwiches – I’m all about the Commuter panini with bacon, eggs and sharp cheddar on sourdough for breakfast and the tuna melt at lunch – and soups, as well as coffee, espresso and other drinks and some tasty baked goods, too. While you’re in there check out all the graffiti penned over the course of well over 100 years of use.
Owner Daniel Sadiq also operates The Full Monty (91 S. Lincoln St.), a pub-style restaurant that is a perfect fit for Sadiq, who is from Britain.
Here, in an intimate setting, is a menu that’s an eclectic mix of Wisconsin and Westminster, with fried cheese curds, steak and ale pie and a range of curry dishes, among other things.
I had the steak and ale pie, which had an incredibly flaky pastry floating atop a hearty steak and ale filling. We both agreed the cheese curds – my kid has spent the summer making great curds at work – are fab gear.
Because I had an under-21 with me, I enjoyed my Pimm's Cup up in the restaurant, but don’t neglect to visit The Underground bar below, which with its dim lighting and low ceiling has an almost speakeasy vibe.
You could, of course, never leave The Osthoff and dine at any of its numerous restaurants.
In addition to room service, poolside dining and food service out on the Lake Deck, there’s the Elk Room Lounge in the lobby with great views of the lake, comfortable seating and a fireplace. Enjoy cocktails and a full bar or specialty coffee drinks and pastries, pizzas and a variety of apps.
Just below is Otto’s, a casual breakfast and lunch spot with omelets, griddles and hashes in the morning and burgers, salads, pizza and more at lunch. Although I didn’t try it, one of my dining companions had the avocado toast, which looked especially good and which is on my radar for next time.
Down the hall, over near the Aspira Spa, is The Concourse Restaurant & Lounge, a more upscale dinner option with dining indoors or out.
We tried some of the steaks – a New York strip and a filet mignon – which were cooked to perfection, and had some excellent appetizers, including braised short rib atop crunchy crostini and a creamy “crabscargo” mix of crab meat and snails in garlic shallot butter with crostini.
For dessert we shared a slice of Reese’s Peanut Butter Cup cake that was insanely rich, with peanut butter filling atop an Oreo cookie crust, topped with Reese’s Pieces and a chocolate drizzle. But warning: this delicious dessert is definitely not made for one. We two adults with notorious sweet tooths could not finish a slice.
When it comes to sweets and especially ice cream, nothing beats a stop of Gessert's, a 1920s ice cream parlor at 99 S. Lake St., in downtown Elkhart Lake, with its vintage interior, including wooden booths, classic ice cream advertising signs and old photos of Elkhart Lake.
But you're really here for the homemade candies – like excellent malted milk balls in a number of varieties – and the wide selection of Cedar Crest ice cream. A treat for all ages.
What to do
One of the first things on my must-do list was to take the opportunity to run on the Road America track, which is open to the public for walks, runs, bike rides, etc. every Monday and Wednesday at 6 p.m.
After trying and failing to do this twice due to weather, I was determined to make it happen this time. However, arriving in Elkhart Lake at the same time as lively thunderstorms did not seem like a good omen. But, like magic, just in time, the storms moved out, leaving it 66 and cloudy, which was perfect for getting in a 4.5-mile evening run.
It was fun to imagine cars zooming around the track which was eerily quiet when I was there, and I encountered only three cyclists and one walker, perhaps due to the weather.
In addition to being America’s National Park of Speed, Road America has motorcycle lessons, go karts, off-roading and all kinds of other fun on tap, too. Check out the website to find it all.
We took advantage of brighter weather the next day and not only hiked an easy section of the serene Ice Age Trail LaBudde Creek Segment – after having walked a different segment on my last visit – but also went up to the Sheboygan Broughton Marsh, where there is a beautiful 30-acre park with a restaurant and tavern, foot golf and disc golf, picnic sites, campsites, a dam on the Sheboygan River that’s fun to check out and an 80-foot-tall tower you can climb.
It’s absolutely worth climbing the roughly 150 steps for the incredible view of the marsh and the countryside and farmland all around.
Some quiet time to just talk and enjoy each other's company was a highlight of the trip.
But with such cooperative weather after something of a washout the previous day, we also took full advantage of the lake, doing a pontoon cruise through The Osthoff Watersports and also renting a kayak.
While the early morning kayak offered serenity and a quiet, introspective time on the remarkably still water, the evening cruise was more social. Even though we were the only passengers on our cruise, the guide – a Sheboygan high school student earning money for college – was friendly and knowledgeable, sharing insights about the lake, the homes that line it and the town.
For an extra-early morning experience we went out for a fishing expedition with Jay’s Guide Service.
Jay Brickner welcomed us onto his 18-foot boat with all the latest fish-finding tech, set us up with some rods and was extremely knowledgeable about fishing on Elkhart Lake, which is no surprise since he’s been leading tours for nearly 30 years.
Despite the fact that he works long overnight shifts at a well-known local cheese producer and had just come off one of those, Brickner was also extremely patient when I managed to somehow tangle up a reel. (Hey, if I was an expert I wouldn’t need a guide!)
Still, all three of us caught numerous fish, including perch, walleye, sunfish and bass; typically lots of fairly small fish but each of us snared at least one roughly 12-inch bass. It was a great experience and something I’d never done at Elkhart Lake before.
Heading out of town, we made a long-overdue return visit to Wisconsin Historical Society's Wade House in nearby Greenbush, which we hadn’t visited in many years ... not since the kids were little.
Wade House is an Italianate inn and home built in 1850 by Sylvanus and Betsey Wade, founders of Greenbush, to serve the passengers of the stagecoaches that traveled on the plank road between Sheboygan and Fond du Lac.
The house is preserved and tours explain the story of the Wades and their home, which was also their business as they housed overnight guests as well as long-term boarders and ran a saloon. In addition, Sylvanus Wade was Greenbush’s justice of the peace and postmaster.
Alongside the house are a working blacksmith’s shop and a recreation of one of the two sawmills that sat nearby, fueled by the waters of the Mullet River.
When about a dozen years ago, Highway 23 was re-routed, drying up visitors to Wade House, which no longer sat on the route, a new visitors center was built to house a cafeteria, shop, restrooms, offices and, most importantly, the unique collection of original carriages built by Sheboygan’s Jung Carriage Works and donated by family member Wesley Jung.
The historic site or the carriage museum would each be worth visiting on their own, but having them together in one place is especially great. The nearly 100 carriages were lovingly restored by Jung and right inside the entrance is a perfect recreation of the kind of stage coach that would’ve run on the plank road and stopped at Wade House.
Even more exciting, Wade House now also has an actual 19th century Wells Fargo stage coach in its original condition, which was donated by Wells Fargo.
You can walk the grounds, or take a horse-drawn carriage from the visitors center to Wade House and the mill and blacksmith shop, where tours are offered at each location. It’s an interesting and educational experience and on a beautiful day it’s even better.
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. A fifth collects Urban Spelunking articles about breweries and maltsters.
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 been heard on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories, in that station's most popular podcast.
