It was a dark, dreary day with overcast skies and a blustery wind out of the north at 15 to 25 knots. Twenty two skippers answered the starting cannon and seventeen hung on to finish at Mackinac Island. The seventeen finishers of that first race went on to become the charter members and nucleus of the Great Lakes Singlehanded Society. It was proclaimed that the organization would be dedicated to the promotion and development of shorthanded sailing on the Great Lakes. Membership would be extended only to those skippers who successfully completed the "Port Huron to Mackinac Island Singlehanded Challenge". The following year, six of the 1979 skippers swore "never again". However, the remaining eleven veteran skippers along with thirty-four new solo adventurers were on the starting line for the second running - all but thirteen made it to Mackinac. The success of the 1980 event firmly established this challenge as a traditional annual event. To date, only 168 skippers have successfully completed the "Port Huron to Mackinac Island Singlehanded Challenge" to become lifetime members of the Society. About half of these skippers have come back to do it again.

In 1981, Ralph Eilberg inspired the ultimate Great Lakes Singlehanded challenge, Port Huron to Chicago, non-stop. There were strong apprehensions about this adventure since no one was aware of anyone completing such a venture along on the Great Lakes. Three skippers committed to the inaugural attempt and all three made it successfully to Chicago. This challenge was attempted again in 1984 by twelve skippers, with the finish relocated to St. Joseph, Michigan. This event was officially called the Huron-Michigan Singlehanded Challenge. Only two of the twelve skippers made it to St. Joseph that year, however, this ultimate challenge had now established itself as an event that would take place every three years. The Challenge has since evolved into its present day form - concurrent starts in Chicago and Port Huron, and finishing in the opposite city. Now known as the Super Mac Challenge, it is the longest freshwater singlehanded race in the world!  To date, only twenty-eight skippers have completed a Super Mac Challenge.

In 1982, the Society established the 40 mile St. Clair Solo. This event primarily was intended to be a means of introducing solo sailing, and a means to prepare for the Port Huron to Mackinac solo. This season finale is well attended by skippers on both sides of the border including a few who are satisfied with an event of this magnitude and are not considering challenges such as the Mackinac solo.

In 1984, the Peter J. Fisher Memorial Trophy was established in honor of our good friend and veteran singlehander who suffered a fatal heart attack during the 1983 Challenge. This award is presented each year to the outstanding skipper in the Challenge based upon his present and past performance in the Port Huron to Mackinac Solo Challenge.

In 1985, members within the Society inspired the Port Huron to Rogers City Doublehanded Challenge. Under the direct sponsorship of the Society, this immediately became a very popular and well attended event. The primary objective was to have fun. Performance recognition awards included many competitive and non-competitive categories. Although the doublehander was conceived within the Singlehanded Society, its potential to become a major Great Lakes sailing event gave birth to the Doublehanded Sailing Association. This new organization became an independent organization to conduct the annual Huron Doublehanded Challenge and other doublehanded events. Despite its independent function, a very strong bond exists between the two organizations.

In 1987, the Ralph Eilberg Award was established. This award is presented in recognition for any outstanding feats of seamanship on the Great Lakes, or upon other bodies of water that have involved members of the GLSS.

Besides sponsoring sailing events, the Singlehanded Society has taken on other activities to promote safe shorthanded sailing. Since 1985, annual safety seminars have been conducted by the Society. These seminars are open to all interested sailors and have attracted over 100 people each year.

In 1993, the Lower Lake Huron Solo was added to encourage solo sailing in the Port Huron, Michigan and Sarnia, Ontario areas.

In 1996, the Board of Directors created the President's Challenge Cup, to be awarded to the first time challenger with the best corrected time in a mono-hull boat.

June 21, 1997 marked another historic day for the Great Lakes Singlehanded Society. The first-ever Chicago to Mackinac Island Singlehanded Challenge was run in conjunction with the 19th annual Port Huron to Mackinac Solo. This race was added as "an equally significant event" and finishers are awarded lifetime membership of the GLSS. The inaugural Chicago to Mackinac Challenge resulted in eight new Members of the Society.

The Lake Michigan Solo Scramble was conceived in 2000 to promote and encourage singlehanded sailing in Lake Michigan. With concurrent starts from both Holland, Michigan and Racine, Wisconsin and a common finish in Michigan City, Indiana, singlehanders on both sides of the lake don't have far to travel to participate, or return to their home ports. It is possible for new skippers to use this race as a solo qualifier for a Mac Challenge or the Sault Ste. Marie - Duluth Solo Challenge, as long as it takes over 24 hours to complete the 110 mile race.

In the fall of the 2002, veteran singlehander Mike Silverthorne lost his life while competing in the Lake Michigan Solo Scramble. Always ready to lend a hand, Mike represented the true spirit in solo sailing. To honor Mike's memory, the Mike Silverthorne Memorial Trophy was established the following year. It is awarded to the skipper who best embodies the exemplary conduct that Mike demonstrated day in and day out, and as such, is only presented by committee recommendation for significant merit.

At the Annual General Membership Meeting held in Chicago in January of 2005, the Membership unanimously voted to sanction a Solo Challenge on Lake Superior. Non-member skippers who successfully completed the inaugural Sault Ste. Marie to Duluth Solo Challenge were granted lifetime membership in the Society, like those skippers who have received a finish in either the Chicago or Port Huron to Mackinac Island Solo Challenges. This Challenge is different from the other races in that the GLSS competes within a solo division, conducted concurrently with the crewed Trans Superior Yacht Race. Unlike the Mackinac Solo Challenges, the Sault Ste. Marie to Duluth Solo Challenge is held every other year (odd years). The inaugural Solo Challenge saw thirteen skippers enter, and there were ten successful finishers. Three of those were non-members who were granted lifetime membership to the Society at the 2006 AGM.

The Lake Erie Solo Challenge became the newest addition to the membership granting challenges sanctioned by the Society when the membership voted to amend the Constitution accordingly at the 2007 Annual General Membership Meeting in Chicago. The inaugural Challenge took place on August 25, 2007, with a start off of North Cape Yacht Club near Monroe, Michigan, proceeding the length of Lake Erie to a rounding of the Seneca Shoal light near Buffalo, New York, and thence to a finish off of Presque Isle Harbor at Erie, Pennsylvania. All but one of the fifteen skippers completed the initial challenge, in which they saw gale force winds in a squall, and significant periods of no wind at all. Of the fourteen finishers, three were first timers, and as a result, they have been awarded lifetime membership in the Society. In terms of length, the LESC ranks third behind the Sault Ste. Marie - Duluth, and Chicago - Mackinac Island Challenges.

With the addition of the Lake Erie Solo Challenge, the Society continues to encourage the development of suitable techniques, equipment and gear for shorthanded Great Lakes passages under sail, and recognize the accomplishments of singlehanded sailors from the Great Lakes region.

Having shared the common experience of successfully completing a membership-granting Challenge, there is a very strong bond of admiration and respect among the Society members. Their friendship is strong and has overcome the barriers of time and distance to be together for the Society's social events. Starting with those 17 skippers that finished the first solo to Mackinac, the Society has grown into a strong vibrant organization that strives to provide encouragement to all sailors who often find that their boats must be handled shorthanded.