"Any damn fool can navigate the world sober. It takes a really good sailor to do it drunk." - Sir Francis Chichester when asked why he carried so much alcohol on his solo sail around the world.


 2021 Bootlegger Races (tentative)

(Only race dates shown. For delivery dates consult the calendar page)

 LMSS Doublehanded Championship (June 10 )

Visit Port Washington -

GLSS Chicago or Port Huron - Mackinac Island Solo Challenge (June 19)

The Mac Solo Challenges consist of the Port Huron to Mackinac Island Challenge (230 nautical miles or 267 statute miles), the Chicago to Mackinac Island Challenge (287 nautical miles or 333 statute miles). The Challenges are held annually, generally taking place on the third or fourth Saturday in June. These two Challenges, run concurrently, and feature a common finish line at Mackinac Island. The President’s Cup Trophy is awarded to the first time finisher on each lake who has the fastest corrected time. An awards luncheon takes place on Mackinac Island on the Wednesday following the start of the Challenges, and non-member skippers who successfully complete either Challenge will be awarded lifetime membership in the Society. (Race registration and more)

82nd Queen's Cup Race (June 25)
Probably with crew, maybe doublehanded

2020 QC e blast header

The 2021 South Shore Yacht Club Queen’s Cup® Race
will be held on June 25, 2021 
and will finish in Muskegon (hosted by Muskegon YC).

 Plan now to enter the 82nd challenge of one of the most storied yacht races on the Great Lakes. This year’s night race across Lake Michigan departs from Milwaukee, WI for Muskegon, MI on June 25, 2021.

Both Milwaukee’s South Shore Yacht Club and the Muskegon Yacht Club will provide an experience worthy of this 83rd Queen’s Cup Race.

The race is open to all boats with a valid 2021 Lake Michigan Performance Handicap Racing Fleet (LM-PHRF) rating certificate and Offshore Racing Rule (ORR) rating certificates. We will continue to have starts for the shorthanded fleet (with a limit of two crew per boat) and a cruising fleet for non-spinnaker monohulls.

We are looking forward to increasing the participation of one design boats such as the J/105, Beneteau 40.7, Beneteau 36.7, and Tartan 10s. The racing between these boats and other one design boats has been close in prior years.

The fee structure is based on boat length. This helps to make the fee schedule more affordable for smaller boats.
Registration will be open and the Queen’s Cup page on the SSYC website will be updated with the Notice of Race (NOR) and other documents by mid-February.

The Course in 2021:

2021 SSYC Queen’s Cup Race … June 25-26

  • Milwaukee, WI to Muskegon, MI and Muskegon Yacht Club.
  • Registration Thursday, June 24 at SSYC: 11 a.m. - 5:30 p.m.
  • Friday, June 25 Registration: 9 a.m. - 1 p.m. Starts staggered from mid-afternoon through early evening.
  • Saturday, June 26 the fleet arrives in Muskegon for post-race festivities hosted by the Muskegon Yacht Club.

Get the latest updates at and ...
Follow us on Facebook

38th HOOK Race (single-handed or with crew  (July 24)


27th Trans Superior ( August 7)

LMSS Q Race (August 14)

The Q RACE – a singlehanded race run since 1981 (now with a double handed section)—takes place approximately every-other year on the third Friday of August.  The next race will take place Friday, August 20, 2021 (tentative date). This singlehanded challenge is intended to encourage adventure, self reliance, and competition in the tradition of singlehanded sailing. While also a race, the primary focus of this challenge is accomplishing the goal of completing the course – relying on oneself, yet enjoying the camaraderie of like-minded sailors. We include a separate division — the DoubleHanded — as an introduction to the spirit of the singlehanded challenge. Additional information will be supplied to entrants.

Course: Approximately 66 nautical miles from a starting line at Racine, Wisconsin, rounding the south NOAA mid-lake weather buoy and returning to a finish line at Racine, Wisconsin.

Notice of Race: Please see the 2019 Notice of Race (pdf) for further details, yacht eligibility, and a printable entry form. Alternatively, you can fill out our online entry form, optionally attaching scans or photos of your race documents, and even send payment via PayPal.

Race Date: Friday, August 20, 2021 (tentative date, check back in 2021)
Entry Deadline: August 4, 2021, unless the limit of yachts has been reached first. Late applications will be accepted up until August 12, but shirts and participation flags may not be available.

Tri-State Regatta - Chicago to St Joseph, MI (Sept 3)
(with crew)