Leave them wanting more
Published on October 29th, 2025
Participation is linked to event format. Long days with many races are great for the serious competitor, but reducing the requirements will typically attract more entrants. In this report by Scott Evans, his season-ending event leaves them wanting more:
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 that recently held its 2025 edition in Milwaukee, WI.
The Dolphin is primarily a Soling event organized by the Milwaukee Bay Soling Fleet but with other fleets/boats invited. Traditionally, 470s participate and has been expanded in recent years to include J/24, J/70, Lightning, and VX One sailors to affirm their love of fun, competitive racing while demonstrating the resiliency of the sport.
After 28 consecutive years of the event, 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. Here’s an excerpt from the 2025 NOR:
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… Bring your boat and your friends for the last great race of the summer. This is the race you will remember all winter! …
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.
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!
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.




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