Brooklyn To Bermuda: The Days Of Seafaring On Gravesend Bay

Gravesend Bay was once home to a vibrant, nationally known yacht racing club. During the summer months, yachts would attempt to out sail one another in our local stretch of the Atlantic, with dapper and sea-faring names like “Wanderlust” and “Flamingo.”

These races would typically commence as soon as the weather would begin to warm up and prizes ranged from cash rewards, to the fame of a victory cup. While races typically were restricted to the reaches of Gravesend Bay, one notable yearly race decided to take it a bit further: Bermuda.

On a pleasant June 6 afternoon in 1908, the Ailsa Craig and Irene II set sail on a 650-mile mission to see which would reach Bermuda in the shortest amount of time.

The race is well-documented by Brooklyn Daily Eagle reports of the day. As the boats first set sail at the mouth of Gravesend Bay, both were cheered on by a crowd of onlookers and cluster of other boats that quickly parted way to make room for the southeastern journey.

The Irene II was the smaller of the two boats, at 40 feet long, and was jokingly likened to a toy. The Irene II, painted white and fresh for the journey, and the larger Ailsa Craig, measuring in at 60 feet, were both made for racing. On either boat, a fleet of five sailors would be overseeing to the boats’ safety and efficiency on their cross-Atlantic journey.

The Irene II shipped out first to compensate for any advantage the Ailsa Craig may have had with its greater length. However, even with this slight advantage, the Ailsa Craig seemed to be able to outmaneuver her companion  — in even the early parts of the race as it quickly took past Norton Point on Coney Island.

The year prior, the Ailsa Craig had defeated another boat in a race to Bermuda and some were already predicting a similar outcome this year. As the two boats continued out of Gravesend Bay and towards the deeper stretches of the Atlantic Ocean, the Ailsa Craig raised its yellow flag, appropriately detailed with the image of a dragon.

Sailing to Bermuda was a difficult and potentially fatal affair. These boats were equipped with only the bare essentials so as to not weigh them down. With only moderate motor power capabilities and often unpredictable north Atlantic winds, the simple yachts could have easily been blown to a pulp of wood in the churning sea. A vague plan was set forth, that should great trouble be encountered, the yachtsman would signal for a cruise liner to rescue them.

When Ailsa Craig arrived at Bermuda 67 hours and 15 minutes after leaving Gravesend Bay, despite surviving the perilous mission, the captain and his men did not yet know if they were again victorious. The Irene II had an extra 20 hours to beat the Ailsa Craig due to a time allowance for smaller and older boats. While it might seem foolish to race boats of varying quality against one another, the quality of a ship’s crew was typically credited with success in a race or mission, rather than the vessel.

In the end, the Ailsa Craig won the fourth annual Gravesend Bay to Bermuda race. A day later, the Irene II failed to show up within the designated time frame and the Ailsa Craig won the cup. Trapped in strong head winds and rough waves, the Irene II was and was unable to make it to the finish line in time.

Long gone are the days of yacht racing on Gravesend Bay or really any past time vessels in these local and storied waters, but one can still imagine the thrill that must have been present, gazing into an open Gravesend Bay.