The Dolphin regatta at Milwaukee

written by Scott Evans  on  October 29  of  2025 and read by 307

The reaching to the mark and Crabcake USA 834
@Scott Evans

Some say sailboat racing is in decline. While there are plenty of signs that this may be true there are also others that say that it is not. One of these positive signs is an annual regatta called The Dolphin held in Milwaukee that just concluded its 28th consecutive running on October 5, 2025.

The Dolphin is primarily a Soling event organized by the Milwaukee Bay Soling Fleet but with other fleets/boats invited. Traditionally it has also included 470s with local legends like Doug Drake and Susie Rieck competing with their high performance dinghies over the years. The tent has been expanded in recent years to include J24, J70, Lightning & VX1 one-design racing stalwarts who are showing up to affirm their love of fun, competitive racing - and at the same time demonstrating the resiliency of the sport.

The 2025 Dolphin concluded 28 consecutive years of the event and it continues to show every sign of still going strong. The history of the regatta is encapsulated in its NOR which was composed in order to remind folks of why they should want to participate. The “official” NOR pretty much speaks for itself as to the purpose. Here's an excerpt from the NOR for the 2025 edition:

“ This is your year! From its humble origins in 1998 as a ‘fun' match race from MCSC to SSYC (loser buys) between a couple of Soling devotees, The Dolphin has evolved through 28 consecutive years to become Milwaukee's premier sailboat race. Over the years The Dolphin has grown to become an annual favorite. Plus, it has proven to be one of the most navigationally challenging races on Lake Michigan – and anyone can win! *

In 2025, the Dolphin Organizing Committee would like to extend a special invitation to our cohorts in the J24, VX1 and Lightning Fleets as well as all other sailboats throughout the Milwaukee sailing community to join in the fun. Bring your boat and your friends for the last great race of the summer. This is the race you will remember all winter!

All boats should be rigged and ready at the South Shore Yacht Club docks prior to 10:30 AM Sunday October 5, 2025. Competitors are required to attend the short yet informative skippers' meeting on the SSYC dock.

This is a fun, free race. Practice sails only! Any sailboat is invited to participate and run the course. There are no handicaps and boats will be scored in their finishing order, unless you make up your own rules. Only a Soling is eligible to win the Dolphin Trophy.

Come one, come all. Bring the boat you've got and drive it like you stole it!

The race course was approximately 6 miles long, winding in and out of the Milwaukee Inner Harbor gaps plus a leg extending approximately 1.5 miles to the southeast to round the Milwaukee Bell Buoy. This was a brilliant last-minute amendment to the verbal Sailing Instructions that enabled a long tight spinnaker reach that created numerous round-ups and broaches (and awesome photo ops from the safety boat). Well done!

The 2025 overall winner was Mike Sabinash on J70 USA1030. Congrats Mike!! The winner of the coveted Dolphin Trophy (awarded exclusively to a Soling) was helmsman Bill Bresser with crew Drew Kosmoski and Clay Feller on USA601, a 1972 Soling with a glorious history that includes Dave Perry. Paul McGuan with veteran crew Mark Keast & Chris Bicenius on USA834 finished close behind in 2nd place and in 3rd place – and also not far behind – was Tom Elliott, double-handing with his equally veteran crew John Bayldon on USA768. Tom and John travel from Chicago every Tuesday night just to race USA768 More Cowbell with the Milwaukee fleet.

Thanks need to be extended to the Milwaukee Community Sailing Center and Milwaukee Yacht Club for enabling this regatta in previous years and South Shore Yacht Club for hosting it this year. This kind of collaboration, instigated by enthusiasts like us, is what sailboat racing is all about and what it should continue to be in order to thrive.



Scott Evans
Current skipper Fuji 35 SV Earendel
Former skipper Soling USA790 & Soling USA737




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The Solings at the race
@Scott Evans

The Dolphin winners
@Scott Evans

The Soling gang at the Dolphin regatta
@Scott Evans