The Wisconsin Golf Trip

Corey Roberson, Director of Golf

After the pandemic stalled our 2020 Wisconsin Golf Trip plans, we were able to reschedule for this August and the trip booked in record time. It’s no wonder. We had the opportunity to play six of the Top 100 golf courses. This trip started out as 7.5 rounds of golf over six days and we managed to turn it into 9.5 rounds of golf!

On Saturday, July 30, I accompanied seven members from the Club on a flight from San Antonio to Chicago. One of the guys on the trip, Jack Dempsey, is a member at a really cool club in the Chicago area called Bob-O-Link Golf Club, so we thought it would be a good idea to start off there. We played 18-holes on Saturday afternoon and then went out for an emergency nine (E9) — this was the first of a few extensions. The E9 was interesting as all eight of us played together in one group and we played a four-on-four scramble. We stayed at Bob-O-Link that night and visited a local restaurant. On SUNDAY, we played another 18-holes at Bob-O-Link and felt the need for another extension, which turned into 18-holes. For this round, we also played in an 8-ball with the same format as the previous day. The best part is that we played in under four hours! To top off a long day, we enjoyed some authentic Chicago deep dish pizza. 

On Monday, we loaded up in a couple of SUVs and headed to Wisconsin, the home of Whistling Straits® and Blackwolf Run®. We played the new short course called the Baths at Blackwolf Run before playing the very difficult River course. The Baths is an awesome 10-hole short course with severe slopes, and the longest shot was 160 yards. A few of our caddies said many guests think the River course is the most difficult of the four main golf courses in Kohler. We ate dinner that night at the Blackwolf Run clubhouse and hit the hay at the Inn on Woodlake. At this point, we’ve played five rounds of golf in three days!

Tuesday was a big day — we started off with an early round at the Irish course at Whistling Straits and followed it up with the highly acclaimed Straits course. The Irish was really cool — another Pete Dye design with large dunes and plenty of bunkers. The nice part was we got to ride in carts as the Straits course is walking only. After a quick lunch at the clubhouse, we pegged it on the Straits course. This was my favorite course of the trip and easily in the top five of my favorite courses of all time. You see the water on almost 

every hole as you are basically meandering on a cliff above Lake Michigan. On top of that, I had one of the best loopers I’ve ever had, played well and the weather was perfect. That night, we had dinner at the Whistling Straits clubhouse and headed back to the Inn on Woodlake. Round count update — seven rounds of golf in four days…you could say we were some tired puppies!

On Wednesday, we loaded up and headed to Erin Hills, the home of the 2017 U.S. Open. Even-though this was the hardest walk (by a wide margin), it was also the favorite course by many in our group. There are lots of sweeping hills and our caddies made the joke, “Just find the tallest hill and start climbing, there’s probably a tee box up there.” We got a little unlucky with the weather as a rain storm blew in and delayed us a couple of hours, but we were able to get out and ended up with a nice afternoon. That evening, we drove 30 minutes down the road to Ocomonowoc where we had some really good Mexican food. None of us were expecting good Mexican food in Wisconsin, but we were pleasantly surprised.

On Thursday, we were all gassed — we’d played eight rounds of golf in five days with one more to go. Our final (or so we thought) round was at Lac La Belle. This is a unique spot as it originally opened in 1892. The golf course that stands today is totally different after the owners of the Prestwick Golf Group completely renovated the golf course and built all new structures. The greens there are super tricked up, which made for an interesting test. After the round, the group decided we needed to play more golf, but instead of hanging out at the putting course at Lac La Belle or playing another nine there, we headed back down to Chicago for an E9 at Bob-O-Link. We had so much fun playing in those 8-balls, we saw it fitting to end the trip where it started!

All great golf trips must have a good lineup of courses — we checked that box. What can really take it to the next level is a great group of guys and we checked that box too! Thanks to Jack Dempsey, Barry Harkness, Bob Curtis, Kurt Talbot, Marc MacAluso, Mark Anderson and Chris Watts for making this trip so special. 

After playing six of the top courses in the U.S., we headed home. Through The Clubs of Cordillera Ranch Signature Vacations, we curated a trip with the same level of accommodations and attention that our members expect while living on the Ranch or traveling with us on a variety of exclusive and well-appointed trips. Our vacation packages are scheduled year-round and designed to appeal to the many interests of Club members. Stay tuned for more experiences through the Clubs.

Corey Roberson is the Director of Golf at The Clubs of Cordillera Ranch. He can be reached at and 830.336.4653.

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