Sean Waldport

My First Ever Golf Road Trip: Wisconsin and Michigan

When was the last time you said “someday I’ll do that?”

Go skydiving? Someday.

Start a business? Someday.

Play all of the Top 100 Golf Courses? Man, that’d be cool, maybe someday.

Screw someday.

Let’s start doing things today.

Introducing the 2013 Breaking Eighty Top 100 Road Trip.

As you may know by now I’ve set a goal to play all of the Top 100 and Top 100 Public Golf Courses as created by Golf Digest by the time I’m 35 (I’m 28 now).

Update December 2022: I’m now 37. Let’s just say, we didn’t hit that goal. And well, the goal also shifted. I’m currently sitting at about half of both the top 100 in America and Top 100 in the World

Since I started this in March I’ve been puttering along, played half a dozen courses and generally felt pretty good about the whole thing.  But half a dozen courses isn’t going to get me anywhere close to my goal.

So I instead of saying “someday” I started saying “what would it look like if?”

And thus, the 2013 Breaking Eighty Top 100 Road Trip was formed.

What is the Golf Road Trip?

2(ish) Weeks, 15+ courses in the midwest, and a hell of a lot of fun.

Starting on September 30th, I’ll be flying into Milwaukee, Wisconsin renting a car, and working my way all over the Lake Michigan area playing every Top 100 Golf Course I can find.

I was originally going to drive from Portland, but it was going to add an extra week to the trip, be more expensive, and only get me another 2 courses.

A big part of the goal is to inspire others to take big action with their lives, and actually do the things they’ve said they want to do “someday”.  I’ll be doing a daily video blog and writing in-depth course reviews with detailed photographs of every single course.

Don’t get me wrong, this isn’t going to be easy, in fact it’s going to be a lot of work.  But who wouldn’t jump at the chance to play so many of the best courses in such a short period of time.  More importantly this will give me the kickstart needed to make significant progress on my goal over the coming years.

The Schedule

UPDATED 9/10/2013.  As I get more things finalized the schedule is evolving:

So the way I look at it, at worst I’ll knock off a dozen new courses and at best I could be close to 20,

How Am I Paying for This?

As I’ve been slowly telling people about my plans a lot of people have asked how I’m paying for this all.

Luckily I’m in a situation with my business where I can work from the road and don’t need to take much time off during this process.  While I won’t be building the business much during this time, luckily it’s relatively low maintenance and so I should be able to keep everything going while I’m on the road.

I’m also taking advantage of lower shoulder season rates, and working with courses whenever possible to get discounted or complimentary greens fees in exchange for the detailed course writeup, video and course promotion.

What About the Weather?

Yes I know, October is getting to be a little late in the season to play golf so far north.  There’s a chance I may cut out some of the most northernly destinations if you know, it’s snowing or something, but otherwise the show must go on!

With such a busy summer this was the time that it fit into my schedule – if it were easy, then everyone would do it πŸ™‚

How Can I Follow Along?

There are a few really good ways to follow along:

  • You Tube Channel – We have a new Breaking Eighty You Tube Channel! This is where I’ll post all of my golf related videos, so check it out and subscribe.
  • Facebook Page – Here you can expect quick notes about the courses, beautiful photos, and all of the other great golf content we put out each and every day.
  • This Site and Email ListHop on our email list for all the updates.

Questions and Feedback

What questions do you have? What do you want to make sure we cover? What do you want to see? This is just as much about making it entertaining for you as it is about accomplishing my goals.  So leave a comment and tell me what you think!


There are 8 comments

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  1. Zach Schaefer

    Have fun! Glad to see you’re playing The Bull. That’s my favorite course (for the money) in Wisconsin. Just played it this past Sunday, shot 85 from the 6,430 yd green tee boxes. I’m about a 10 handicap, so if you’re a 7-8 I’d say go for the 6,800 yd blue boxes, if you’re a 10-15 stay at the greens. You can also go for the blacks if you want, but it’s a whole different world back there.

    • Sean Ogle

      Awesome man, I’m really excited – it’s the first course I’m playing and I’ve heard nothing but good things. I’m about a 14 handicap, so probably going to be migrating towards the greens on this one πŸ™‚

  2. Jon

    I’m surprised you don’t have Cog Hill #4 on your list for Chicago courses. Might be that you have played it before, but it is super accessible and very challenging. Also, I hope you have some connections for Butler National because it is a tough tee time to come by. I have heard nothing but amazing things about the course, but never had the privilege to play it. All in all, I think your list of courses is impressive and I’m excited to see how your trip unfolds. Good luck and hit ’em straight!

    • Sean Ogle

      I actually played Cog Hill when I was out there in May, had the whole course to myself and it chewed me up πŸ™‚

      Yeah I’m finding all of the Chicago private courses to be tough. I got really lucky and met a member at Medinah on that last trip, and I have someone who could get me on Olympia Fields, but they said it’s $300 and many of the bunkers are under repair – so I’m a little hesitant…

      Thanks for the support!

  3. Arjan Vera

    Good luck with your trip. I will follow all of it and hope to learn from your adventures, as I will start my own road trip in April 2014; ‘365 DAYS OF GOLF’.

    My goal: playing golf 365 in a row on a minimum of 365 different courses through Europe.
    website in progress:

    Once again good luck Sean.


  4. My Interview With Lifestyle Entrepreneur Sean Ogle

    […] Ultimate Golf Road Trip – I’m on a quest to play both the Top 100 Public and Top 100 Golf Courses in the world, and knew I had to find a way to start knocking off courses. So I found the area of the country with a high concentration of courses, rented a car, and played 15 rounds in 15 days. It’s every golfers dream […]

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