My visit to Oconomowoc, WI was my first non-work related trip out the Mid-West. Just like I am with most places, I was really surprised. I flew in to Milwaukee, and Leigh and a couple of her long time friends picked me up from the airport. They took me to this awesome Irish Pub out in the 3rd Ward, which was along the water. The entire area looked like it was going through some urban gentrification. I could understand why. The 3rd Ward is right along the water and has some old abandoned buildings that were what I imagine used to be warehouses that were used for export. In most places this would be prime real estate, and for the 3rd Ward of Milwaukee, it looked like it was on its way.
During dinner where there were tons of cheese to be consumed. I would expect nothing less from Leigh’s friends in terms of cheese intake, as there is no one I know that loves it more than my girl from Wisconsin. After dinner, we visited Leigh’s childhood friend, Brad, at a restaurant he manages for dessert. From here I was able to catch the end of game of the Lakers/Celtics Finals game while we all shared the restaurant’s well known IceCreamtini that was the size of all of our heads. Yes, even my massive head.
After a nice evening in Milwaukee, Leigh and I drove to her hometown, Oconomowoc. ‘O-town’ as I’ve hear it referred to a few times is a really charming former lake resort town where lots of the brewing families such as Pasbt and Miller used to own vacation homes. Spending time in Oconomowoc felt like spending time in Plesantville. Everything is so well taken care of and everyone really does seem to know each other. One night, we went to dinner at one of Leigh’s friend, Stephanie’s family restaurants, and it took us 20 minutes just to walk to our table because her mom literally stopped at every table to say ‘hello’ to someone she knew. This small town is charming in so many ways, but that’s the one thing I appreciated most. It really felt like a community where although I’m sure everyone is in each others dirt, it definitely felt comfortable and inviting.
One of the highlights of the trip was going to The Kiltie. Leigh worked at this old fashioned carhop from high school through college, and it was a big part of her life. How do I know? Every opportunity we had, she wanted to go to The Kiltie. This was pretty awesome. I got to see where Leigh spent most of her days growing up. I even got to meet her old boss, Drew, who came all the way out to the car to greet me with a very charismatic ‘Sconnie’ accent.
I was sad to leave Oconomowoc and the lakeside room that Leigh and her mom put me up in. I don’t think I’ve ever been more relaxed. We really didn’t do much there, but that was the entire point. I’m really happy that I got to see where Leigh grew up; as it gave me a lot of insight into who she is. And how can I forget, it was also incredible to get to know the dynamic duo of Mary and Muggsy (Leigh’s mom and OCD dog).






| July 28, 2010 @ 1:23 pm
Mary B says:
Hey Nam! Love your insight on Otown. Hope you are planning to come visit us again! I will have lots of cheese and Kitlie custard waiting for you. Maybe even a Pabst beer! And by the way, Mugsy was diagnosed by the vet with OCCD which of course is Obsessive Compulsive Canine Disorder! I am thinking she would fit right in (or right under Leigh’s desk) at GSP so may send her on an extended visit to San Francisco. Hugs from Mugsy and Mary B