What’s the best private golf course in the state of Wisconsin?
While the CH Alison designed Milwaukee Country Club has long been the clear #1 in national rankings, there’s always been a 1-B for me: Pine Hills in Sheboygan.
Lacking a world-famous architect, this 1928 Harry Smead design just down the street from Blackwolf Run still slides under the radar, even being considered by many a hidden gem in the midst of the Sheboygan-area golf mecca.
Who’s Harry Smead?
While Smead is only credited with two solo course designs in his career, it’s widely believed he worked for the legendary duo of William Langford and Theodore Moreau, and the proof appears to be in Pine Hills’ adventurous greens complexes.
Like Langford & Moreau’s Links course at Lawsonia, Ozaukee Country Club in Mequon or the front nine at West Bend, Smead throws out conventional wisdom at Pine Hills including the placement of five par threes with four par fives, two of which come back-to-back early on the inward nine including the 453-yard 12th whose par is defended primarily by its tough-to-hit, then wildly undulating putting surface vs. the more conventional determinant of distance alone.
Pine Hills’ topography is on par with anything I’ve played in the top 100 of the world’s leading golf publications, its conditioning is immaculate and layout superb. There’s not a weak hole on the course nor a shot players can take off.
Where it shines more than anywhere, though, to me is on its par threes. The variety Smead designed in its par threes is incredible, including the long uphill fifth with its massive, internally contoured putting surface, the long downhill seventh over the Pigeon River that I fished with my grandpa as a child, the mid-length uphill 16th whose surrounding land is currently in the process of being exposed to show its brilliance, the short downhill 14th and the star for me that is the ninth.
Played over a ravine near the clubhouse, the green on nine is one of the most severely sloped I’ve ever played making this short par three anything but a simple pitch and putt. The first time I played Pine Hills, in fact, we had a solo member play through our group on nine. After cheering for him hitting the front-left of the green from the tee we watched as he took six more strokes to hole out, even putting off the front of the green.
While Pine Hills has always been an extraordinary golf property it’s faced many of the same challenges all Wisconsin golden age courses have, most notably the encroachment of trees around its playing corridors. One of the country’s largest inheritors from the Imprelis herbicide debacle, Pine Hills has never been afraid to reinvest in its golf course.
Reinvesting in the golf experience
Recent updates and renovations by Drew Rogers have made this Kohler-area course even better, most notably by taking what was its weakest golf hole and making it a world-class finisher. Time had seen tree lines force an anxiety-ridden mid- to long-iron off the tee for most players on 18, finishing the round with a tee shot that was unlike any other on the course: Not fun. Rogers’ redesign cleared out the massive hillside, exposing site lines across the property and allowing players to choose their own adventure on what’s now a thrillingly strategic right-to-left Cape Hole rewarding long, accurate hitters with a short approach into a mostly unchanged, ever-dramatic elevated greens complex abutting the clubhouse.
Together with the split-fairway downhill 17th, Pine Hills now has a memorable finishing duo of holes that rivals any in the state and always has me pining to return for more.
Who’s #1?
Is Milwaukee still the clear-cut best fully private club in Wisconsin or will we see a dark horse like Pine Hills someday rival it in state and national rankings? Does its lack of a quote unquote historically significant architect hold it back vs. Milwaukee’s world-famous CH Alison or should it not matter? Milwaukee is spectacular in every way, as well, and has done an amazing job of consistently updating and reinvesting in their course, but I’ve always felt the two are much closer than golf media gives them credit for, and the off-the-charts fun factor at Pine Hills has always nudged it to my personal number one.
The wild card here, of course, is with the newly reborn Lido at Sand Valley Golf Resort. Is it a private club as Sand Valley suggests? Is it a public course because of the tee times made available to its resort guests? If it’s considered private then it relegates both Pine Hills and Milwaukee to the number two and three positions, but probably fairer than anything is to consider it in a class of its own. The Lido is a true one-of-one, a historic recreation of what was once one of the world’s greatest golf courses brought back to life in Central Wisconsin using incredible modern technologies and a perfectly resurrected pre-existing blueprint. Rightfully so, The Lido debuted in the top 70 of GOLF’s Top 100 Courses in the World in 2023, and it will never look back.
Will Pine Hills find its way onto these esteemed lists someday? I believe it should, and while much of the rest of the world is still catching up to its brilliance I think it’s a matter of time before we start seeing it emerge in national Top 100 rankings, as well.
No matter where you rank them, the debate of Milwaukee vs. Pine Hills vs. Blue Mound vs. The Lido vs. Stevens Point, Kenosha, West Bend, Minocqua, Oneida and others pays credence to something we here know as a fact: Wisconsin has some of the world’s very best golf and it’s only getting better.
Our day at Pine Hills Country Club
Our day at Pine Hills began early. I set a 3:15 alarm to get on the road and be there for a 5:02 sunrise and ensuing golden hour. After driving through miles of dense marine layer nearing the Sheboygan area, my hopes were dwindling for a great photo shoot but arrived ahead of schedule at 4:45.
Pine Hills’ new Head Golf Professional, Andy Smith, met me at 5:00 to talk and help get carts situated, and WiscoGolfAddict.com Contributing Writers Brian Murphy and Rich Bauer met up with us shortly after.
The fog at Pine Hills that morning was thick and impervious – and it didn’t burn off until after 8:00. We sat in the basement bar watching coverage of Scottie Scheffler’s early morning arrest at Valhalla, peering out the window to see if any trees were visible yet or if any sunlight was beginning to hit tee markers or other objects within 20 feet and in view.
Finally, around 8:00 we could start to see a few things and made our way onto the course for morning photography. With a 9:00 tee time we only had about 45 minutes, making me happy to have two other photographers along with me to help cover as much of the course as we could during an excellent “shadow session.”
Our foursome consisted of Brian, Rich and my friend and WISN-12 Sports Director, Dario Melendez, who I’ve gotten to know over the years through our annual Wisconsin vs. Illinois Writer’s Cup series, as well as at occasional golf media events. Dario’s game has come a long way since the first time we teed it up together, by the way, and we had what turned out to be a really fun group for our day at this historic Wisconsin private club.
The Golf Course at Pine Hills: A Few highlights
Similar to the nearby Bull at Pinehurst Farms, in my opinion the start at Pine Hills is strong but less memorable than the holes that follow once players get into the property’s woods and rolling hills.
The first at Pine Hills tees off from near the practice range to a wide, rolling fairway that climbs more than aerial photos give it credit for – it’s heavily crowned and drops toward rough on both sides before rising to an oversized greens complex.
Short (376 from the blue tees and 360 from the whites), the opening hole at Pine Hills is a bit of your proverbial friendly handshake to open a really, really fun round of golf.
Just slightly longer than the first, the second at Pine Hills plays back toward the clubhouse and is set wonderfully against the club’s US flag – a delightful bit of Americana and beautiful backdrop to toast while trying your best to hold this challenging putting surface and avoid the bevy of sand traps that surround it.
The third is a three-shot par five that runs alongside the club’s tree-lined entryway. With a slight right-to-left bend, players going for it in two will need to hold a shallow (from back-to-front) green that’s significantly elevated and bordered behind by trees… with a very long club.
This is an excellent par five.
A long par four, the fourth plays downhill to a wide fairway that again has a little right-to-left in it. The right side of the playing area is bordered by trees and a small creek runs most of the length of the hole on that side.
Another elevated greens complex, the fourth’s is one of the most built up on the course with just one bunker to avoid short-left.
To me, the fifth – a long, uphill par three that plays between 190-220 yards to one of the course’s most unique greens – is where the round starts to get truly remarkable.
The front-right side of the green on five is raised and the front-left lowered, creating a false front, while the left side then falls away to two lowered traps. About halfway through the putting surface, then, comes a lateral trench dividing the green and running slightly towards the back.
I’ve always had good feels on the fifth. I almost had a hole-in-one on it from 218 yards a few years ago and had a solid par this time around, but it’s certainly the kind of hole with potential to give players fits.
The sixth is a short par five that plays over a ravine to a fairway that bends slight right to left and finishes in a low spot abutting the forest and a ravine. Go long on six and you’re dead. Lay up too short and you’ll be hitting a touchy sand shot from an awkward distance.
Seven is one of the best par threes on a course with incredible par threes.
We played the white tees during our recent round but had to take the opportunity to hit from the tremendously elevated blues. While the tees are perched high above the river – about 50 feet from tee to water – the green is well-risen and makes the actual elevation change from tee-to-green only about 20 (thank you, Google Earth Pro, for the assist!).
From this distance, though, the green looks like a miniscule target, and is crowned with roll-offs all around.
A lot of my favorite photos of Pine Hills have come on this hole over the years, especially from behind the green looking back up toward the teeing complexes.
The eighth is a fun par four that I found a new challenge on this time while playing from the white tees. We’ve always played the blues in the past, which require a tee shot to the fairway. From the whites, though, it’s just over 250 yards to carry the river and get home under regulation.
While my attempt to hit it in one failed miserably, Dario hit a great tee shot here, clearing the river and leaving a short but next to impossible chip shot from the right side.
This green is sneakily one of the toughest on the course – everything on the right side is raised with humps on the outskirts and the left side runs off into bunkers and collection areas.
For a short four, the eighth presents a ton of inherent challenge!
Following the par four eighth we get to one of my favorite holes on the course, the par three ninth.
A short par three played over a ravine abutting the clubhouse and driving range, the green on nine (as I described earlier) is absolutely insane.
If visiting Pine Hills for the first time, take note these directions when leaving nine: Park your cart in the roundabout by the ninth green, grab your driver and golf ball and walk behind the clubhouse near the pool. Grab a beer, hot dog and/or Johnsonville brat at the window or bar and then proceed to the tenth tees outside the bar windows. You cannot drive to the 10th tee box.
Featuring another incredible view over the golf property, the tee shot on 10 is visible from the pro shop, bar/restaurant and back patio, so don’t even think about the river flowing down the left side of the fairway or the trees down the right that will block out approach and recovery shots if pushed.
Maybe the most challenging shot on the course at Pine Hills is the approach on 10. With an elevated greens complex situated against a hillside, there are sand traps everywhere – all unseen from the low-lying fairway area. Don’t go long for risk of a lost ball, and don’t be short as you’ll then be facing a touchy recovery shot toward the hazard.
One of the most interesting stretches begins on 11 where Smead designed back-to-back par fives that could not be more different.
The 11th is a long but fairly straightforward par five with a little right-to-left fairway bend. It has a narrow green protected on both sides by bunkers and a false front, but is otherwise nothing too crazy.
The 12th, on the other hand, is wild.
The tee shot plays to a rollicking fairway that runs right to left and favors a long draw. Hit the short grass and you’re in great shape on the approach, but miss it and you’ll be facing a recovery shot that should be one thing: safe.
The putting surface on 12 has very few level spots, if any, and has steep banks and run-offs all around. The green-side traps, built in a style nearly identical to Langford & Moreau’s traditional flat beaches with steep, sod-faced walls, are well below the green surface and leave blind recoveries.
I don’t think I’ve ever two-putted this green before, and unfortunately three-putted it again during our recent round en route to double bogey on one of the shortest par fives you’ll find anywhere.
As I mentioned above, this par five is unconventional in that its par is not defended by the traditional determinant of distance, but by challenge – especially with its green surrounds.
Playing uphill between tree lines, the 13th is a mid-range par four that finishes on a green with a tall, steep left side bank. Stay right on the approach to avoid it.
The shortest par three at Pine Hills, the 14th features a beautiful downhill tee shot to one of the course’s smallest greens bordered to the left and right by sand.
Added points on 14 for the covered wooden storm shelter over the cart path, and yes I know I accidentally called it the 15th in the following video…
15 at Pine Hills has been worked on significantly over recent years, removing trees from the right side to make the creek more visible and give the hole a more open look and feel.
The creek, while visible from the playing surface, is narrow and windy, and really should not come into play often. It’s the green on 15 that should grab your attention. Long from front-to-back, it’s heavily canted and requires a good approach.
16 has always been what I’d consider to the least exciting par three at Pine Hills, but I have a feeling will end up being anything but.
The course has been removing trees at a rapid clip on this hole, starting to expose the terrain’s sizable ridges and scenic topography. This has taken the 15th from being a tree-surrounded hole to being one that now better shows off its land (I’m told more de-treeing will continue) and puts its crazy greens complex front and center on this uphill shot.
Following 16 we get to one of the most special one-two punch combinations of golf holes in the entire state of Wisconsin: the left-to-right 17 followed by the right-to-left 18.
The architecture on these two holes is spectacular, and it all plays out in players’ minds in a choose-your-own-adventure style of golf that puts finishing a great round strong squarely on your shoulders.
From 60 feet above the fairway, the elevated tee boxes on 17 provide views of the “safe” fairway below it, as well as the Pigeon River that dissects the playing surface vertically and right-side fairway leading to the green.
While players can set themselves up with a short approach shot in on 17 with a long fade, it’s also putting the opportunity for a lost ball into play. I did just that during our recent round, smashing driver into the center of the Pigeon with the straightest shot I hit all day.
17’s green is another great example of Smead’s steam shovel architectural prowess, internally contoured throughout.
The most exciting change at Pine Hills Country Club since the last time I reviewed the course in 2013 is on 18.
As I wrote about in July 2020, the club hired golf course architect Drew Rogers to make thoughtful revisions to its acclaimed layout, and first and foremost among the “issues” they faced was on the finishing hole.
The previous 18th just didn’t fit. This is a fun golf course with fairly generous fairways, long site lines and strategic play. The 18th offered none of that with its tree-infested layout.
Rogers’ renovation (concept shown below) changed that, incorporating an old school Cape Hole design.
The tees were relocated, the dramatic hillside along the fairway was almost entirely razed, the tree line right and beyond it was cut back and the hole’s fairway was expanded to allow for a greater variety of shots and more strategic interest.
The 18th always had a great greens complex so nothing was changed there, but it’s now visible from everywhere on the hole.
The 18th at Pine Hills is now a great finishing hole, and the combination of 17 and 18 might now be Wisconsin’s best two-hole ending stretch.
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
#18 at Pine Hills Country Club 
My approach on 18 – my only birdie of the day 
#18 at Pine Hills Country Club in the morning fog
In a recent Instagram post about Pine Hills, Club President Keith Robel asked a commenter what he thinks would be “fair” to charge non-members for a [likely once/year, though it was a completely hypothetical question] round on an esteemed private course. His reply was probably around $200.
Given where it’s located and the prices being asked for and paid at nearby Kohler courses (all well over $300/round), I’d expect it to be higher. At very few golf properties I’ve visited can you get an experience as fun, challenging and memorable as at Pine Hills, and as more of the world continues to find out about it I think its mystique will only continue to grow.
After all, it just may be the best private golf course in the entire state of Wisconsin.
Pine Hills Country Club website
What do you think is the #1 private golf course in the state of Wisconsin? So nobody’s left out, I’m including all 57 of the state’s private clubs according to Google searches (some may now be semi-private or public as I have yet to play them all).
Nice article, Paul – it was a great day on a marvelous golden age gem! I’m glad we got some nice photography even with the foggy start. The work they are doing at PHCC is amazing.