Standing at the counter with a cookie in one hand and a chocolate in the other, my playing partner Dylan Dethier called to mind a kid in a candy store. Except he’s an adult — and the candy was complimentary. So were the sandwiches. And the ice cream. And the beer. It was nearing noon on a clear autumn day, and we were easing through a round in a sylvan setting, on glassy greens and impeccably groomed fairways, rolled through corridors of oaks and pines. This was parkland golf at its most pristine, at a resort course that carries the hush and polish of a private club. We were free to proceed at our own pace, with no one visible in front of us, no one pressing from behind, and the latitude to linger at refreshment stations stocked to please all tastes with sandwiches, salty snacks, craft beers, top-shelf booze and confections worthy of Willy Wonka.
In short, we were playing golf at SentryWorld.
In recent decades, Wisconsin has become one of the country’s marquee destinations for the game, home to more public-access Top 100 courses than any other state, including the major-championship layouts of Kohler and Erin Hills, and the minimalist marvels of Sand Valley, Bandon’s Midwestern sibling. But long before that boom there was SentryWorld, the original spark of Wisconsin golf wanderlust and an essential stop on any Badger State itinerary. Conceived in the early 1980s by then–Sentry Insurance CEO John Joanis as a tribute to the landscape and community that gave rise to the company, it was designed by Robert Trent Jones Jr. on gentle terrain ornamented by lakes and mature trees.
Among the standout holes are the cape-style par-5 5th, which wraps daringly around a lake, and the par-3 12th, playing to a green set on a watery peninsula. But none are more photogenic—or more famous—than the Flower Hole, a par-3 ringed by 50,000 blooms. Jones calls it his “Mona Lisa,” — a sign even says so by the tee — and it’s hard to argue with the description: a kaleidoscope of color in a landscape painting come to life. The hole is replanted every spring, just before Memorial Day, by a crew of 20 to 25, who take three days to complete a job that brightens the property throughout the season.
Those factoids were supplied to us by director of golf Danny Rainbow, about as aptly named an executive as you’ll find in the game. As Rainbow explains, SentryWorld’s appeal lies not just in its conditioning and its spectacularly colorful hole but in its character — its quiet, uncrowded rhythm and sense of welcome that set it apart. “The experience is different than any other in the state,” he said of the spread-out times, parkland design and culinary oases. “That’s not to say it’s any better or worse than other style of golf course. It’s just a great mixture to work into any Wisconsin golf trip.”
Like the game it celebrates, SentryWorld has never stopped evolving. In 2013, ownership doubled down with a full renovation, and in 2021 it opened The Inn at SentryWorld, a handsome 64-room boutique hotel just off the course. That same year, Jones and his team gave the layout a tune-up in preparation for the 2023 U.S. Senior Open. The result is a course that blends resort comfort with tournament rigor—immaculate surfaces (sub-air systems hum beneath the greens), 20-minute tee intervals that make it feel like you have the place to yourself, and those abundant refreshments stations, one set between the 1st and 10th hole, the other positioned between the 3rd and 13th, allowing for multiple stops throughout a round.
When we weren’t stuffing our faces, Dylan and I made a friendly match of it. He’s a former mini-tour player who still plays to a plus-3 handicap. I’m a six index with a jerryrigged swing that makes me look like I’m shooting 100. But I’m also too proud to take strokes. Thanks to the flexibility of Jones’s design, Dylan pegged it from more than 7,000 yards while I took it on from closer to 6,000, an advantage I accepted in lieu of strokes. He still beat me 1-up — though I like to think I edged him in the calorie count.
If you somehow finish a round at SentryWorld without being well-fed, that’s on you. The Library Café offers coffee and light bites in a serene setting, while PJ’s — a wood-oven bistro with a wraparound bar and breezy patio — attends to heartier cravings. Across the road from the resort, beneath Sentry’s corporate headquarters, Muse serves refined dishes in a space with a speakeasy feel. It’s reachable by elevator, hidden behind an unmarked door, and adorned with (yes, seriously) Picassos and Calders on the wall.
The next morning, we woke early and did what any golf junkies on a buddies’ trip would do: pressed repeat. Another round, another stop (or four) at the refreshment stations, capped by another meal worth remembering. By the time we packed up to leave, the scores had blurred, but the impressions hadn’t. Golf is a game. But on and off the course, SentryWorld treats hospitality as an art.
