Do long voyages on tumultuous waters, troublesome weather a’brewing, and passing sea-faring enemies in a race to the finish mean anything to you? No, we’re not talking about a children’s book filled with pirate adventures; we’re talking about the Wednesday Night Sailboat Races that launch from City Dock during the spring through the end of summer. You don’t have to be a sailor or even understand the slightest bit about sailing and boating to enjoy these free races. You can simply watch from the starting line and wait in anticipation for the boats to finish at the Harbor. We have the scoop on the past, present, and future of this Annapolis tradition.

The Annapolis Yacht Club hosts these races and, quite impressively, initiated the races after observing the East Greenwich Yacht Clubs’s Wednesday Night Races in Rhode Island. The Annapolis Yacht Club’s site, www.annapolisyc.com, tells more about this history: The year was 1959 when Gaither Scott, who was once a commodore, named Wednesday the racing night at the yacht club here. If you add it up, that’s 55 years of sailing and racing on Wednesday night–it’s quite the tradition. Back when Scott started up the races here in Annapolis, they were not for prizes or score but were essentially entertainment and a good thing to do on otherwise mundane Wednesday nights. Now of course, the sailing is certainly charged with a racing spirit and trophies are awarded to the winners. In the fall, the Annapolis Yacht Club also passes out overall performance awards to those sailors who demonstrated their capabilities.

Not nearly as attended at its inception as it is now, the races have grown to include a upwards of a stunning 125 vessels. The race goes on for a couple miles as participants make their way through the Chesapeake Bay and then turn around for a challenging finish through the Harbor. It’s quite easy to watch both the start and the finish but the finish is arguably more thrilling as sailboats in the race must manuever through docked ones already in the Harbor. At the starting line, the first fleet of boats are already up to speed when the gunshot signal is fired. As the race goes on, more fleets get the go-ahead to race. This staggered start prevents accidents and keeps the racing fair. You’ll see all sort of boats, large to small, with names like “Crash” and ones probably named after family members.

If you participate in the race or are a member of the Annapolis Yacht Club, there is a get-together after the race with food, drinks, and good times at the clubhouse. Truly, it’s incentive to join as a member. The club also has opportunities for young sailors like the International Junior Sailors program.

As for the future of the races, the tradition will continue many Wednesdays from now. After all, what would Annapolis be without sailboats, racing, Annapolis Yacht Club, and free entertainment from the Dock?

The races begin on Wednesdays in the early evening, a bit after 6 p.m. The racing concludes around 8 p.m. Take a camera, binoculars, and some friends to participate in this long-established Annapolis activity. For more information, head to the site above.