In the summer of 1905 Guy B. Hiltz went for a "spin" on Louisbourg harbour in his new yacht while crowds watched from the shore. The "Sharp" was 20 feet long on the deck and designed and built by Wylie Stacey who had recently opened a boat building shop in Louisbourg. Within a year Stacey would employ 3 people and complete 5 vessels. His fast boats made Louisbourg a contender in Cape Breton’s sailing world.

In late August 1906 the Stacey-built "Maggie" won first prize in the fishing boat race in Baddeck. The win encouraged local people to promote a Labour Day race on the harbour and they invited boats from Port Morien to Gabarus to come to Louisbourg. The Sydney Record noted that " with good boats such as there are, and with good men to sail them, such as our fishermen are noted for, and an excellent place for a race, a very interesting and exciting race can be got up."

On Labour Day, the Louisbourg weather started out threatening but the storm held off. The sailing event for the day was a sloop-rigged race which Thomas Wilcox won easily, beating out 10 rivals.

In mid September, 17 sloop-rigged fishing boats raced on the harbour. The course was from a wharf at the foot of Minto Street, around a buoy at the Old Town, round the bell buoy off the lighthouse and back. The wind was light on the run to Old Town, but freshened on the return, making it a race for 5 of the boats. W.H. Townsend’s boat, sailed by Fletcher Townsend, placed first, Bert Wilcox came second, Joseph McDonald in Patrick Campbell’s third, Thomas Dickson, in John E. Tutty’s, fourth and Michael Williams fifth. The first prize, donated by Mayor Lewis, was $7.50. The success of the event set in motion plans for a sloop-rigged fishing boat race at Thanksgiving.

This enthusiasm must be viewed in the context of the times, of the various racing meets around the island, and of a booming and optimistic Louisbourg in the first two decades of the 20^th century. The coal company’s S&L railway came, bringing prosperity, work and new people. Louisbourg was established as a town with mayor and councillors and there was talk of a railroad from St. Peters. There were new homes and businesses constructed including a Marine Hospital, new glebe houses and manses. The fortress ruins were being stabilized, a brass band was formed, and a few years later the Marconi wireless receiving station was established. It seemed that the 20^th century was Louisbourg’s century.

The 1907 boating season opened on Victoria Day with harbour races featuring yachts built during the preceding winter in Wylie Stacey’s boat house. These included Duncan Crowdis’,"Ivanhoe" and John A. McDonald’s, "Marion."

Formal races were set for Dominion Day, and visitors came to Louisbourg by the morning train. In addition to watching the races, they could also tour the ruins of the fortress where D. J. Kennelly was directing the repair of the ruined casemates. Luck was not with our sailors, however, for as the yacht races started the wind died and the event was cancelled.

Not discouraged, the enthusiasts planned races for Labour Day. They were optimistic because that summer, for the second year running, a boat designed by Wylie Stacey - "Ivenhoe" - won the Commodore’s Cup in Baddeck. According to the Sydney Record "Captain Crowdis got the rooster for 1907."

Races for Labour Day 1907 included fishing boats no more than 35 feet long, fishing sloops and first class sloops rated as yachts. The yachting prize was a silver cup which had to be won two years in a row in order to keep it.

The starters and judges were W.E. McAlpine, John Matheson, Joseph O’Toole and Paul Bates. For spectators from outside of town there was a special-price ticket on the S&L.

The day began ominously with a downpour of rain and little wind. But, by mid morning the sky cleared and the day turned out well with a fresh breeze from the north east. The first race was the doubles rowing match over a 2-mile course with 5 entries vying for prizes of $5, $3 and $2. D.W. McDonald and George Wadden came in first followed by William Grey and Patrick Lahey. The other boats were crewed by Captain Jenner and Henry C. Verner, Charles Hunt and Charles Beaver, Fletcher Townsend and Bert Wilcox.

In the schooner-rigged fishing boat challenge there were three entries racing for prizes of $20, $12 and $8. The first prize went to the "Maggie" owned by A. Kennedy of Little Lorraine and sailed by its builder Wylie Stacey. Second place went to the "Arthur Severance," of Fourchu, sailed by Gordon Stevens and third to the "Fearnot" sailed by Samuel Tanner.

There were 15 entries in the fishing sloop race. The course was from the freight pier, around the bell buoy off the light and back. Fraser Wilcox was first, then Bert Wilcox, Dave Tutty and Charles Dickson.

Five yachts entered the 1st class race. They were: John A. McDonald’s, "Marion" sailed by Fletcher Townsend, "Louisa" sailed by Dan Fleet, "Ivanhoe" sailed by Duncan Crowdis, "Vera" sailed by Dr. Freeman O'Neil and "Sharp" sailed by Guy B. Hiltz.

The favourite was "Ivanhoe" fresh from winning the Commodore's Cup in Baddeck. But it was Fletcher Townsend in the "Marion" who won the silver cup in Louisbourg, a sweet victory since "Ivanhoe" had won over the "Marion" in Baddeck by a mere 18 inches. Three of the five yachts racing that day were of the same size and lines and all built by Wylie Stacey.

The last race involved six tubs vying for prizes of $1, 50c and 25c. In the final field of four, Fletcher Townsend came first followed by Abe Wilcox and Charles Dickson.

Throughout September and October, on Saturday afternoons, Louisbourg yachts raced on the harbour, watched by an interested and anticipating population. By mid October the standings were 2 wins for the "Marion," and one each for the "Louisa" and "Ivanhoe" with 2 more races planned.

The Louisbourg Yacht Club was formed in September 1907 with 26 citizens joining the first night. Officers included: Dr. Freeman O'Neil, commodore; W. W. Lewis, vice-commodore; Duncan Crowdis, rear commodore; and A.A. Martell, secretary-treasurer. The governing board included the officers plus Captain P. J. Wilcox, H.C.V. Levatte and Joseph O'Toole. The racing committee included Capt. W. P. Cann, Fletcher Townsend, Wylie Stacey and G. B. Hiltz. The commodores were asked to draft designs for flags, and plans were made for sloop and schooner-rigged races.

The creation of the Louisburg Yacht Club opened the door for more than racing. In early October the Club sponsored a "very elaborate ball" in Peter's Hall on Main Street. The event was open to members and friends. At the dance held in November it was noted that " a large number of strangers from neighbour towns attended the function."

The last race of the season was held on Thanksgiving Day. In addition to local yachts racing for a cup there were races for fishing boats. A celebratory turkey supper was served at the yacht club rooms, which were in the coal company office buildings on Main Street near the railway overpass.

There was great anticipation for the opening of the 1908 season. Yachts owned by Duncan Crowdis, John A. McDonald, Capt W. P. Cann, Vincent O’Toole, Fletcher Townsend, R. Kerr, Michael Mackenzie, John Dillon and Mr. Fleet were to race.

On Dominion Day the weather was good but the wind was light so the races did not prove as interesting as they might have. There were six yachts racing with Fletcher Townsend's the best by 10 minutes. In addition to the yachts there was a sloop rigged fishing boat race with 6 boats from Louisbourg and 2 from Lorraine. The Lorraine boats claimed the day, Fraser Wilcox coming first followed by John Fiander, then Thomas Wilcox and Michael MacKenzie.

This was the beginning of a summer of sailing. The Baddeck Yacht club races were coming up and four yachts left Louisbourg for Baddeck. These were: John A. McDonald's, "Marion," Duncan Crowdis', "Ivanhoe," D.P. Cann's, "Donald" and the "Aeolus" owned by Fletcher Townsend.

The visit to Baddeck was a successful one for Louisbourg for Fletcher Townsend's yacht won the 8 mile race on each of three days coming away with the cup and cash prize.

Racing went on during the summer of 1908 in preparation for Labour Day. Meanwhile the captains of the "Ivanhoe" and "Marion" with several others planned to go to Sydney to race for the Cibou Cup offered by the Royal Cape Breton Yacht Club. The tug E.M.Cates towed the "Aeolus," "Ivanhoe," "Marion" and "Donald" to Glace Bay where they were turned over to the Steamer Gladiator and towed into Sydney.

In Sydney it was the "Aeolus," that "succeeded in lifting the silverware and all the honours that went with it." The Cibou Cup was Louisbourg’s again.

On their return, the tug E. M. Cates towed the yachts from Scatterie into Louisbourg. The boats were met at Townsend's wharf by an enthusiastic crowd and "when the steamer and her yachts rounded the point there was a great screaming of whistles from the power house, the coal engines and the steamers in port. Flags were displayed from many buildings and the Norwegian steamer Hermod were gaily dressed up in bunting. The yacht crews were given a great ovation on landing."

The events for Labour Day 1908 included a schooner-rigged fishing boat race, fishing sloop race, yacht race and "an exciting" tub race. The weather was not pleasant with a south wind, occasional rain squalls and fog. Still, the morning train brought visitors in from outlying areas, a steamer brought out 70 people sponsored by the Port Morien Masons and the races went on as planned. J. Dillon’s yacht was the early favourite but Fletchers Townsend’s "Aeolus" won, followed by J. Reid, John Dillon, John A. McDonald and, trailing the pack, Duncan Crowdis’ "Ivanhoe."

But smooth sailing is rare and there were problems with the fishing boat races. Dickson’s boat came in first but because of a time allowance Stacey won. There are no details but the news paper reported " considerable dissatisfaction in some quarters over yesterday's races and it is said that there will be few if any fish boats compete in any races here in future."

The gossip that fall, as the yachts were taken ashore for winter, was that the "Marion" owned by John A. McDonald had been sold. There was speculation that McDonald was going to have another yacht built to compete against the "Aeolus."

The 1909 season opened in the spirit of friendly competition. Fletcher Townsend, the 1908 winner, set the challenge by flying a flag with a picture of a rooster and 1908 inscribed on it. According to the newspaper it " fluttered from the main peak of the Aeolus as she glides over the blue waters."

On Dominion Day there were harbour races on and, once again, the weather was bad. The sloop race included Fraser Wilcox from Big Lorraine, Archie McDonald's sloop "Helen" sailed by Fletcher Townsend and Michael MacKenzie's "Idle Hour" sailed by Arthur Townsend. As in 1908 Wilcox won the race, followed by the "Helen" and 5 minutes later the "Idle Hour."

There were only three yachts racing in rainy weather. They were the "Aeolus," the "Marion" and Dillon’s yacht. During the race the "Marion" broke a mast and the "Aeolus" won. After the races the Methodist Ladies provided dinner at Wylie Stacey's boathouse for visitors.

At the end of July the "Aeolus," the "Marion," and yachts owned by D. Cann and R. Kerr left Louisbourg to participate in the Cibou Cup race in Sydney. From Sydney the yachts moved on to Baddeck for races in early August.

The "Aeolus" was all round winner, gaining the Cibou cup in Sydney and the Commodore’s cup in Baddeck. The Sydney Record opened its column by saying, "Hats off to Captain Fletcher Townsend his sturdy crew and gallant little craft Aeolus, a jolly combination from the Louisburg Yacht Club which on Saturday afternoon successfully defended the Cibou Cup against all comers in an invitation jaunt for 17 footers over the R.C.B.Y.C.'s fifteen mile course." There were six yachts in the race which took place on a warm sunny day with a stiff north west wind blowing. John A. McDonald and the "Marion" crossed the finish line in second place. D. Cann’s "Sport" took 5^th place.

Back in Louisbourg there were expectations that yachts would race on the harbour for a cup donated by James Ross of the Dominion Coal Company. The race was cancelled however since bad weather would not permit the yachts from Sydney and North Sydney to get to Louisbourg. Finally, on Labour Day, there was a race for Ross’ President's Cup. Only three yachts sailed the course. In first place was the "Aeolus," then a yacht owned by Mr. Kerr and then the "Marion." There were also races for schooner rigged and sloop-rigged fishing boats. As usual the S&L provided a special train to Louisbourg, there were visits to the fortress ruins and the cornerstone of the new Masonic Hall was laid.

From the annual meeting of the Louisbourg Yacht Club in June 1910 there is a list of officials. They included: Dr. Freeman O'Neil, commodore; W. W. Lewis, vice-commodore; Porter J. Wilcox, rear commodore; A. A. Martell, secretary; and Neil Murphy, treasurer. The sailing committee included, G.B. Hiltz, Alonzo Tutty, George Lewis, Roderick Kerr (flag captain) and A.W. Stacey (official measurer). The managing committee was H.C.V. Levatte, Norman McRury, D.J. Matheson, D.W. McDonald and Joseph McDonald.

There were no yacht races on Dominion Day because of lack of wind. The newspaper reported waters "as placid as those of a small lake." But there were motorboat races with three entries: W. W. Lewis, A. Stacey and Lewis Cann. The Lewis boat won.

Again in 1910, for the third year running, Fletcher Townsend's "Aeolus" won the Cibou Cup. Two other Louisbourg yachts the "Argo" and "Marion" were there and placed 3 and 5. There were no races on Labour Day and the Sydney Record for 8 September notes that "the yacht racing fever seems to be on the wane among the active sports of Louisburg."

It was not until 1912 that the Cibou Cup was returned to the Royal Cape Breton Yacht Club. That year the race on Sydney Harbour was won by S. J. Dobson, ". . . thus bringing to Sydney the cup, which ever since its donation has remained at Louisbourg."

In 1913 in Baddeck, the "Aeolus," "Marion III" and "Osprey" represented Louisbourg. "Marion III" was a new boat built John A. McDonald from designs of George Owen It won the first race of the Aeolus Cup for Louisbourg. According to the Beinn Bhreagh Recorder, "The win was a very popular one, as the Louisbourg yachtsmen have done more than any other club toward keeping up the interest in the Aeolus Cup."

On July 27, 1914, two weeks before the outbreak of World War I, the Cape Breton Yachting Association held the first race of its season in Louisbourg. Though started, the race was called off due to poor winds. The cup was awarded to F. W.(Casey) Baldwin, of the Bras D’or Yacht Club, sailing "Scrapper II," since he had completed the first leg of the race and had won the race the year before. The following took part in the last yacht race on Louisbourg Harbour. "Scrapper II," F.W. Baldwin of Bras d’Or Yacht Club, "Haydea," Lang of North Sydney, "Cibou II", Dobson, Sydney, "Vsato," Jack Barrington, North Sydney, "Marion III," John A. McDonald, "Aeolus, Fletcher Townsend, and "Extenue."

With the coming of war interest in sailing meets on the harbour waned. John A. McDonald went to Sydney and Baddeck to take part in races in 1915, but there is nothing else mentioned. It would not be until the 1930s that racing on the harbour, this time with motorized fishing boats, would draw local attention.