"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.


 2022 Bootlegger Races (tentative)

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

 LMSS Doublehanded Championship (June 9th )

The 2022 LMSS Doublehanded Championship – The “Doublehander”, or “Double”, is a double-handed race run every year, usually on the Thursday of the second full week of June. Our 36th annual Double will start on June 9, 2022. This race is intended to encourage adventure and competition in the tradition of shorthanded sailing and cruising. The Doublehanded Championship will consist of a race to Port Washington, Wisconsin. June 10, our layover day, will be in Port Washington where the Port Washington Yacht Club and Sailing Magazine will be our hosts. A party and an awards ceremony are planned for that afternoon. Your race fee includes the Port Washington Yacht Club party (and luncheon), dockage in Port Washington, and two T-shirts if your entry is timely.

Awards: There will be classes for monohulls, with awards for first, second, and third place in each class. There will be a class for multihulls if at least three enter. There will be a minimum of five and maximum of ten boats per class, at the discretion of the race committee.

The Course—East-Shore Division: 66.5 nautical miles/76.5 statute miles from a starting line at Muskegon, Michigan, by any course, to a finish line at Port Washington, Wisconsin. Starting will commence at 0800 (local time) June 9, 2022.
The Course—West-Shore Division: 53.5 nautical miles/61.5 statute miles from a starting line at Winthrop Harbor, Illinois by any course to a finish line at Port Washington. Starting will commence at 0830 (local time) June 9, 2022.

Notice of Race: Please see  2022 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: Thursday, June 9, 2022
Entry Deadline: May 25, 2022. Late applications will be accepted up till June 2, but may not include the free T-shirts or a participation flag.  (registration, NOR, results, etc)

Visit Port Washington -

GLSS Chicago or Port Huron - Mackinac Island Solo Challenge (June 18)

The Mac Solo Challenges consist of the Port Huron to Mackinac Island Challenge (230 nautical miles/267 statute miles), the Chicago to Mackinac Island Challenge (287 nautical miles/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.

HOOK Race 2022 Death’s Door Challenge  

(July 16th, Singlehanded) 


Saturday, July 16, 2022

The HOOK Race is a 189 nautical mile (217.35 statute miles) race on Lake Michigan held each year in July. The challenging event starts outside the harbor in Racine, Wisconsin, “hooking” through Death’s Door (Porte Des Morts passage), a narrow and often treacherous passageway between Washington Island and Wisconsin’s Door County Peninsula, continuing across Green Bay, and ending in Menominee, Michigan.

The Racine Yacht Club is especially excited to be offering for the very first time a Super HOOK option for the race. Competitors wishing to return south ASAP or to prepare for the CYC Mackinac Race can add this option to their HOOK Race entry and compete for a second finish. This Super HOOK option will provide competitors with the longest race on Lake Michigan at 379 nautical miles.  See our HOOK website for details.

The first HOOK was sailed in 1984 with 12 boats. It was envisioned as a shorter and less expensive alternative to the Mac. The race grew to over 70 boats until 2020 when COVID 19 forced the cancellation of the Mac. In 2020, over 100 boats registered for the HOOK and the number of registrants was capped at 100. That year Thunderstruck, a Farr 60 owned by Rick Hennig, set a new course record of 21 hours, 9 minutes, 3 seconds of elapsed (uncorrected) time. Rick Hennig broke his 2020 record with a finish time of 20 hours, 20 minutes, and 46 seconds with Thunderstruck in 2021. Firefox, a Hunter 54 owned by Mark Westdale held the previous record in 1987 of slightly less than 24 hours of elapsed time. 94 boats started in 2020 and included five PHRF divisions, five One Design divisions (J 109, J 111, Beneteau 36.7, T10, S2 9.1), a Double Handed division, and the unique Cruising (motoring allowed, with restrictions) division. In prior years the HOOK also featured a Single Handed division and a Multi-Hulled division.

Events for the HOOK start Friday night before the race at the Racine Yacht Club. There’s a rum party, dinner, live entertainment, and a skippers’ meeting. On Saturday morning the Cruising division’s first warning is at 0830 hours followed by the racing fleet’s first warning at 0855. The elapsed time limit is 56 hours from the last division (PHRF 1) start. The finish line is between the Race Committee trailer on the north end of the pier at Menominee Marina and a large lighted inflatable buoy. Monday evening post race events in Menominee include a rum party, entertainment, and the awards ceremony.

All divisions including Cruising division competitors, One Design divisions, and multihull divisions require a PHRF certificate. The Cruising division is designed to give first time HOOK racers a taste of the competition and the race course. You may use your motor only as far as Chambers Island in Green Bay and must record your motoring time (which, of course, counts against you). Single Handed division sailors must show evidence of a prior 24 hour solo passage, completion of a LMSS (Lake Michigan Singlehanded Society) solo challenge event, or GLSS (Great Lakes Singlehanded Society) membership.

The 2020 HOOK was exceptionally challenging due to heavy winds and weather. It received national coverage and sailors gave it highly favorable reviews.

The 2021 HOOK set new records due to favorable weather.

Come join us for the first or even 39th time in 2022!

Ed Palladino and Fred Stritt

2022 HOOK Chairmen  (registration, NOR, results, etc)

2022 HOOK Race Tracking:


There & Back Short-Handed Regatta (August 6)

The race is open to any sailing vessel. There will be a single-handed section and a double-handed section. The race course will be along the Chicago shoreline and will be approximately 45 nm in length for the long course. The short course distance will be set the morning of the race and is between 14.5 nm to 24 nm. The race will start near the mouth of Belmont Harbor at 08:00 CDT and will finish by 20:00 on the same day. The finish will be near the Belmont Nun buoy.  (registration, NOR, results, etc.)   (Flyer)

LMSS Solo/2X2 Race (August 19)


SOLO / 2X2 – a single-handed race run since 1981 (now with a double handed section)—takes place usually every other year on the third Friday of August.  The next race date is Friday, August 19, 2022.  This single-handed challenge is intended to encourage adventure, self reliance, and competition in the tradition of single-handed 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 double-handed 2X2—as an introduction to the spirit of the single-handed challenge.

Course: The course for 2022 is from Racine to Muskegon weather buoy (45161) to Mid Lake weather buoy (45007) to Racine. A distance of approximately 144 nautical miles. The weather buoy marks are to be left to Starboard.

Personal Qualifications: Solo entrants must be experienced sailors. Entrants who have completed previous Solo races are automatically qualified. Other entrants must provide evidence of experience, including a documented single-handed passage of at least 50 miles and including a statement of other experience sailing or racing offshore. New entrants will have until August 13, 2022 to complete the 50-mile passage.

Notice of Race: Please see the 2022 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 19, 2022
Entry Deadline: August 3, 2022. Late applications will be accepted up till August 16, but may not include the free shirts or a participation flag.   (registration, NOR, results, etc)

Tri-State Regatta - Chicago to St Joseph, MI (Sept 2)
(with crew)
GLSS Solo Scramble (September 16)
The 2022 race will have three separate starts: Chicago, Holland, and Racine. All starts will round the Lake Michigan southern weather buoy and then proceed to the finish in Michigan City, IN.
" The Solo Scramble is sponsored by the Great Lakes Single-handed Society to
encourage the excitement and adventure of solo racing with others who enjoy the
challenge, camaraderie and special sense of accomplishment inherent in single-
handing port to port. It also encourages the enhancement of sailing skill and problem
1400 CDT from Racine Yacht Club

1400 EDT from Macatawa Bay Yacht Club (Holland, MI)

1400 CDT from Columbia Yacht Club (Chicago)

Macatawa and Racine to the NOAA South Weather Buoy rounding it to Michigan City, IN. Distance approx 105 miles

Chicago To the Tri State boarder rounding it to Michigan City, IN.

Distance 104 miles
Registration, NOR, results, etc. : 

 Louie's Last Regatta (September 24)
(with crew)
Details will be posted when available