By Bob Tagert

Annapolis, Maryland and the Wednesday Night Races

I have sailed into Annapolis Harbor for many years, mostly on my sailboat but also on others including the 125 foot Schooner Alexandria. The sight of the U.S. Naval Academy has never failed to impress me as well as the sheer number of sailboats on the water. This is why Annapolis is known as the Sailing Capital of the United States. On this particular trip however, we would not be sailing, but were guests of Carl and Tulinda Larsen, longtime friends, aboard their 50 foot trawler, Skylark. Our destination was to anchor one end of the starting line for Wednesday Night Races and also serve as the committee boat. And more importantly , it was also a birthday get together for Tulinda and Lani.

The Wednesday Night Races have been a time honored tradition in Annapolis for nearly 60 years and the Annapolis Yacht Club has been the host for every race. “What better way to break up the week than a relaxing evening out on the water?” said John Sherwood, a legendary Chesapeake Bay sailor and longtime Annapolis Yacht Club member, “I can’t imagine doing anything else on Wednesday night. It’s part of the weekly schedule.” Annapolis sailors do not take their sport lightly!

In addition to the 130 or so sailboats that participated in the race, there were also dozens of spectator boats that lined the course to watch the competition as the boats hoist their colorful spinnakers and asymmetrical sails. The finish of the race can also be observed in Spa Creek from the comfort of restaurants like the Chart House and Carol Creek if the wind cooperates. But we were here to observe the race from the committee boat and learn a little bit about what goes into a race like this.

Actually, this is not one race, but can be up to 10 separate races, all featuring different classes of boats. Each class has its own starting time and the faster boats start first so the classes stay separated as they sail out into the Chesapeake Bay. On Skylark there were at least 8 volunteers working the start of each race and being observant of any boats crossing the starting line before the horn sounds for the start. In addition, there are another 22 volunteers that help monitor the races from the start, duration on the course, around the marks and the finish boat.

Each class has its own signal flag that is flown on the Signal Boat (Skylark) so that each captain can see where the race stands even though there is radio contact from the Signal Boat as to starting times. The timing and organization of this spectacle is incredible and very smooth.

After the boats return to their slips the crew members make their way to the Annapolis Yacht Club where there is a party including drinks and food and also a video recording of the race for the crews to enjoy. During the entire race there is a crew out filming every start in order to replay all of the action. The best we can do is show the photographs from our afternoon on the Signal Boat.

The second part of this road trip is the town of Annapolis itself. Like Old Town Alexandria, Annapolis is an old seafaring town along the banks of the Severn River and the Chesapeake Bay. It is also the State Capital of Maryland and home to the United States Naval Academy. The Main Street of Annapolis runs from the City Dock along Ego Alley up through town to Church Circle. Like Old Town, former warehouses have been converted into fine shops and great dining establishments. Some of these establishments have come about in the past ten or fifteen years, but some have been there since I started going to Annapolis 45 years ago.

Down by the water front on Dock Street you can find McGarvey’s Saloon & Oyster Bar as well as Middleton Tavern. Both of these classic taverns have anchored the waterfront for decades. The Annapolis Market House is also located in this end of town. Located in the next block on Main Street is O’Brien’s Oyster Bar & Seafood Tavern. This place has been a favorite of ours for a long time. In the next block is the famous Chick & Ruth’s Deli. This is a favorite breakfast and lunch stop for locals and visitors alike. In the next block is Castlebay Irish Pub. This is a very popular pub and if you are lucky, our friends, The Eastport Oyster Boys might be in the house playing their “songs of the Chesapeake”.

These are just a few of our favorite spots in Annapolis. It is indeed a beautiful town with a lot of history and charm. You can get there by land or by sea and you won’t be disappointed. However, one disappointing note here is that after we got all of this done, I learned that the Wednesday Night Races ended on August 28^th. On the upside, however, the Frostbite Sunday Races will commence in November and you can watch the end of those races from one of the restaurants that border Spa Creek. Regardless, there will be a lot of sailing in September and it is a beautiful time of the year to visit Annapolis. I hope that you enjoy the photos.