Wednesday Night Racing offers sailors and spectators active sporting and friendly competition
It’s a Wednesday night in peak summertime, which means several hundred sailors will head out of Annapolis Harbor for an evening sailing race. Anywhere from 125 to 150 boats participate in this weekly ritual. The Annapolis Yacht Club has been hosting Wednesday Night Racing (WNR) since 1959. The concept has been become popular across America. The idea is for informal type racing for sailors of all skill levels and ages. Additional local sailing organizations host weeknight racing on other nights, but Wednesday is the premier event. On Tuesday nights small dinghies race and on Thursday nights a variety of J Class fleets compete.
The Annapolis Yacht Race Committee starts the first of ten classes at 6 p.m. sharp. The racecourse takes the fleet out into the Chesapeake Bay before returning to Annapolis Harbor with the finish line adjacent to the club house right next to the Spa Creek Drawbridge. Spectators can get a good view of the action as the racing boats sail past the Naval Academy, City Dock, along the Eastport waterfront and the bridge. On windy nights it can be exciting as sailors execute last minute maneuvers and often have close finishes. Competitors will tell stories of being comfortably in the lead and sadly losing the race in the final quarter mile. Conversely, other sailors will make a heroic come-from-behind finish. The result is always in question during the race, and that keeps crews humble and hopeful.
The Harbor 20 class debuted ten years ago in Annapolis and has become a popular boat. Most Harbor 20 competitors tend to be on the mature side and, yet, are still very competitive. The Harbor 20s place a starting line closer to the harbor and usually race on a shorter course. This competitive class will feature several overlapped boats as they cross the finishing line.
Overall, the idea for weeknight racing started in New England after World War II. In the mid-1950s, the late Gaither Scott was visiting Rhode Island and was intrigued by a weeknight series he witnessed at the East Greenwich Yacht Club on Narragansett Bay. Scott, along with sailing enthusiasts, Jack Martin and Howard Benson, liked the idea and started an informal series hosted by the Annapolis Yacht Club. The club’s archives state the racing was not very serious, but people enjoyed getting out on the water while the sun was high late in the day during the summer season.
A fleet of racers sail into the Annapolis Harbor on a Wednesday night.
Inevitably, the racing became a little more intense; after all, the thrill of winning is in our human nature. In the mid-1960s, boat yard owner Arnie Gay, along with Larry Newark and Al Bruce, organized more formal racing in several classes and gave the winning sailors trophies. The club started a tradition of serving an informal dinner after racing. The social event became a big draw for families. Many young sailors got their first taste of racing on Wednesday nights.
Top sailors used the weeknight series as practice sessions and crew tryouts for the more serious races that took place on weekends. As the years passed, weeknight racing has become more important. The Annapolis Yacht Club breaks the summer into three separate series with awards presented to the winner of each series. Victory is a treasured feather in a sailor’s cap.
Summer weather and wind conditions can vary dramatically week to week. On some nights a delightful summer thermal breeze will power the boats with 8–12 mile-per-hour winds. The air is warm and the sailing ideal. On other nights there is not a breath of air at all. On these slow nights the race committee will send the fleet back to the harbor after a short wait of thirty minutes or less. And, then there are nights with thunderstorms. Every sailor watches the skies carefully when threatening clouds build up. Lightning is dangerous especially when strong winds arrive with the storm. If there is a serious threat, racing will be cancelled. The race committee will issue a cancellation notice two hours before the scheduled race. This seems to be happening more often in recent years.
Wednesday night races have competitors sail out the Annapolis Harbor, into the Chesapeake Bay, and return for a dramatic finish.
Annapolis and the surrounding area are a fast-paced region. Road traffic is heavy throughout the day, and people seem busy everywhere one travels. Keeping pace with this lifestyle, the exercise of preparing a boat for racing in a short period of time can be frantic as people rush from their jobs to be on the water. The sailors have little time to tune up before the Wednesday night race begins. Once the boats cross the starting line and head for the bay, a beautiful sense of relief arrives and everyone relaxes. Sailors get a sense of freedom as they race for the turning marks. Sailors are determined to improve their boat’s speed while trying to gain an edge on the competition. The cadence of commands and communication is short and focused. Crews understand what is needed. Within a few minutes of the start, every sailor is sailing efficiently. Many young people feel honored to be invited onboard and probably do not realize they will continue this routine for many years in the future.
Once the sailors are back on the land after racing, any on-the-water tension is long gone. The discussion revolves around the shifting winds, capricious currents, efficient crew work, stories of hardship and triumph, and most importantly, a feeling of satisfaction of being on the water with a happy crew. The races only last an hour or so, but the experience shortens the week and like a siren’s call brings sailors back just seven days later.
This year’s Wednesday Night Racing concluded at the very end of August. This September, fall races begin and, in due time, the winter Frostbite Series will resume. More on these races in an upcoming issue. To learn more now, visit annapolisyc.com/racing/regattas.


