My First Iceboat: Jerry Simon & ESMERELDA

Photo courtesy Jerry Simon     ESMERELDA, a Madison-style Stern-Steerer. Jerry Simon, right, with his aunt and cousin.

Previous: Paul McMillan: My First Iceboat
4LIYC Renegader Jerry Simon received a letter this week from Tim Murray (see below) that made his day.

ESMERELDA was my first iceboat purchased by my parents in 1955 to distract my interests in motorcycles. They bought the boat for $200 from the Bill Rider family, who lived on Lake Monona in Monona, Wisconsin. This picture was the only one I had until the Tim Murray picture arrived.


I am standing next to my aunt Dorothy Chambers, with my cousin Larry both with skates on. The photo was taken off of Yahara Street Park on Lake Monona at the end of Dunning Street in Madison. We sailed out of this park back then and had to carry boats down rock embankment to get on the ice. The iceboaters welcomed us younger guys because lots of labor was needed to take and set up the boats.


Bob Brockel, Harry Fields, and other neighborhood kids were happy to help, hoping for a ride. Phil Sawin would park his “Land Lark” motor home on the grass, which became our headquarters when not on the ice. His white iceboat was called “ICE LARK” and was likely made by the group of early Four Lakes Ice Yacht Club sailors such as Tom Krehl, Paul Krueger, Dave Rosten, Bill Ward, with Bill Mattison and Jack Ripp’s guidance.


As to the name, there were several, depending on the day’s outcome on the ice, but “ESMERELDA” sticks. She was big and slow and would toss you out if you didn’t treat her right—one big momma. We had the most fun when it was windy, sometimes with two or three aboard and one on the end of the plank. The boat slid around because it was impossible to sharpen the runners with my tools. She would spin easily, tossing us out as we would peel off the wind and lose steerage.

Another problem was that the metal bobkin would break off when sailing over rough ice, so I made a wood pattern and cast an aluminum one. Tim Murray’s letter mentions that the boat sat too low on the ice, especially under the mast. Modifying a Carl Bernard creation was not a good idea.


I used her for 2-3 years before buying Jack Ripp’s 2nd Class A Skeeter (a modified Renegade) that I named “PAR-A-DICE.” The Skeeter was faster, lighter, and easier to set up. I’m not sure who bought ESMERELDA from me, but I faintly remember a family off Morrison Street in Madison.


Knowing that Carl Bernard built many Madison-style iceboats, it was likely one of his. Someone said he made nearly 100 over the years in the Bernard Boat Shop, which is now the Hoover Boat House owned by the City of Madison, next to James Madison and Conklin Park.

The Madison-Style Stern Steerer before Jerry Simon owned it. Tim Murray is next to the tiller.

Via Tim Murray:

I came across a slide that my Dad took in the mid-1950s of the iceboat you bought from Bill Rider. My Dad took the photo soon after Bill purchased the boat for his son Gary, my age. The four people on the boat are Dick and Harold George (both deceased), Gary Rider [deceased), and me at the tiller.

I know my Dad took this photo soon after Bill purchased the boat because the boat was already set-up when Bill bought it. The next winter Gary and a few of us set it up once we had good ice. We did not support the middle of the plank correctly when putting it together.


Gary’s idea was to cut some inches off each of the angle planks between the runner plank and the upper plank. I told him not to do that because something just wasn’t right, and we needed to figure it out. Against my advice, Gary proceeded to trim a few inches from each board to fit them in the notches. The modifications caused plank to lose the crown, which meant the boat barely cleared the ice. Rider’s lived on Winnequah Road, so we always had to man-handle the boat when crossing the pressure ridge that ran from roughly Tonyawatha Trail where it meets Winnequah Road to the old ESBMA building on Monona Drive. Dave and John Rosten had to do the same as they lived just a few blocks north of Rider’s.


1922 Madison Winter Carnival on Lake Monona. Photo courtesy Marv Luck.

The 1922 photo above is difficult to write about because there is so much history captured at that moment. Pictures like this can send one down a never-ending rabbit hole of history. It’s tough to stick to one topic when there are so many presented in this photo, such as Madison’s history, the history of each boat and skipper, and the differences between the Hudson River and Madison styles of Stern-Steerer. For this post, I’ll try to stick to the subject of DORLA.

A 4LIYC Facebook member in Madison recently asked about the Stern-Steerer DORLA because her family had a connection to the boat. Marv Luck of Oshkosh, who knows the big ships’ history better than anyone, noticed the request and handed me a couple of 8 x 10 photos of DORLA last weekend at the Puckaway Nite and Renegade regatta.

DORLA was owned initially by Henry Meyer of Pewaukee, WI. I’m not sure who built DORLA, but I would guess John Buckstaff of Oshkosh, WI. (Marv can correct me if I’m wrong.) The Meyer family was heavily involved in ice sailing in the first half of the 20th century, and Henry served as Secretary and Treasurer of the Northwest for several years.

The newspaper reports about the 1922 Madison Winter Carnival don’t mention DORLA, but that’s undoubtedly her in the photo because the picture came from the Meyer family. The Capital Times reported on February 3, 1922, “…to make the ice boat races a feature of the Carnival, the Four Lakes Ice Yacht Club has received acceptances of a challenge from the Ice Yacht Clubs at Pewaukee, Oconomowoc and Oshkosh. Several Hudson River types of ice boats will be in the fleet of boats from Pewaukee and Oconomowoc. Suitable trophies consisting of cups and pennants will be awarded the three winning boats: in three different classes.”

Henry Meyer and DORLA won three Class A Stern-Steerer titles in the Northwest Regatta in 1928, 1930, and 1931 and the Hearst Trophy in 1931 and 1932. I have found no mention of DORLA until 1947.

In 1947, DORLA appeared again in a Wisconsin State Journal report about the Northwest. She had become part of the Four Lakes Ice Yacht Club Stern-Steerer fleet and was owned by O. T. Havey and sailed by Phil Oetking. In 1948, the same newspaper reported that Havey’s boat had placed second in the Northwest regatta under a new name ELECTRA. Of course, Havey gained fame as the man who commissioned the MARY B Class A Stern Steerer. In 1956, the boat was called DORLA again with a new owner, 4LIYC member Johnny Adams.

DORLA might have ended up with the same fate as so many old Stern-Steerers, quietly decaying in a barn until put on a burn pile by people who had no idea of her regatta titles and rich history.