Racing Down the Chesapeake

I arrived at the dock on a cloudy Wednesday morning at 9:30am to board Woodwind and meet my fellow crewmates. There were two captains, Jen and Mickey, two navigators, Ken and Rai, four paid staff crew, Chris, Courtney, Dallas and Delaney, and four guest crew, Brett, Chris, Gene, and me. I was the only relatively inexperienced member of the party. Captain Jen showed me around parts of Woodwind I hadn’t seen before below deck, including the berth where I’d be sleeping. She also showed me how to strap into my sailing harness, which I’d be required to use at night regardless of the weather.

The wind was very light, so we cast off and motored up the bay. Once we got a little bit north of the Bay Bridge, the sun began to come out, the wind grew a tiny bit, and we set sail. The crew soon set the spinnaker, the light racing sail that generally replaced the jib when the winds allowed. After some discussion among the experienced sailors, a second spinnaker was hoisted for practice. While this was going on, Chris, Courtney, and Dallas worked with me on tying knots. While I’d learned a couple knots in sailing class, I definitely had not mastered them, and I needed a lot of practice to feel moderately secure I could tie a bowline knot. Even then, I don’t believe I tied a knot during the whole trip without someone watching to be sure I was doing it correctly.

We continued up the bay past the Magothy River and Baltimore Light, all while the crew experimented with the spinnakers. Jen fixed the first of a series of astonishingly delicious meals that we had while underway, a cold shrimp noodle dish. It turns out she can cook as well as she can sail! Soon we reached the Key Bridge, where we saw a helicopter with two people hanging down from it, working on some equipment fixed near the bridge. We all marveled as the helicopter suddenly flew off, the two people still hanging from it, dangling behind.

We passed the marker that designates the place where Francis Scott Key wrote his Star Spangled Banner poem from a ship near where the bridge now spans. Then we focused on Fort McHenry and the city of Baltimore from an angle I’d never experienced before.

At about 3pm we arrived in Baltimore at Anchorage Marina. Most of the other schooners had already arrived. We took some time on the dock to admire the schooners. An old dancing friend, Stacey, called to me from the boat she keeps at the marina, and she showed me her boat and talked to me a bit about sailing. She also showed me the schooner she and her significant other, Rayned, would be sailing on during the race, the Jolly Dolphin.

Then came the Parade of Sail, during which the schooners paraded around Baltimore Harbor. The professional crew brought out the small cannon and got to fire it several times for show as the other boats fired their cannons in answer. The guest crew and several others that joined us enjoyed some beer and snacks on the boat. The winds were too light to sail, but the sails were set for show while we motored around the harbor.

Dinner catered from Mission Barbeque came next. The whole crew ate and drank beer together and mingled with the crew from other boats. Of particular interest was the tiny sailing replica of the huge Pride of Baltimore, which was a quite tippy little schooner that I’m quite sure would only be fun to sail in light air. After a shower at the marina, I headed for my berth, where I spent my first night ever on a boat. I slept surprisingly well.

When I awoke in the morning, many of the schooners had already set off south for the start line near Annapolis. Again the air was light, so as we had our morning coffee, we were obliged to motor back past the Bay Bridge to get there. On the way we passed the Coast Guard barque Eagle, a large training vessel, motoring the other way. Dallas worked with me some more on knots. Jen then prepared huge sandwiches for us before manning the helm for the race start. Courtney inadvertently made us laugh when she emerged from below with one of the sandwiches, tripped on a step, and spilled the contents of a sandwich. As she reassembled the sandwich, she announced that it was not hers, but Mickey’s. Mickey accepted the reassembled sandwich with good humor. Generally the crew was full of good humor, and I felt no real tension between members of the crew during the whole trip.

The race start was quite hairy, but Jen and the crew managed it amazingly well. The wind remained very light, while a current pulled the schooners too quickly towards the start line, and several schooners passed it early. The violators were penalized with a requirement that they bring their boat around 360 degrees, making it difficult to ever catch up. Meanwhile, the captains and navigators agreed that the best route for Woodwind would be to cross the shipping channel and sail on the eastern portion of the bay, the current being more favorable there. The sailors also agreed to set the second spinnaker to take advantage of what wind they could find. I’m sure we were a curious sight with our two spinnakers. I’ve yet to see a photo of Woodwind from a distance while both spinnakers were up, but photographers did come near the boat to take pictures. At this point we began to pull ahead of the Pride of Baltimore, which we left on the west side of the bay.

We continued in light wind throughout the afternoon, moving at only 2-3 knots. I manned the jib for a short period. To pass the time, crew members told stories. I’ll never forget Courtney trying to tell a ridiculously wandering shaggy dog story that made even me groan. As dinnertime neared, I steered for the first time during the race. I sailed to the compass, with occasional navigational changes as determined by the navigator. The sun set with colors of pink and purple. We ate a dinner of pasta and salad, after which I steered some more in the dark.

By this point we had been divided into watches of 1 captain and 4 sailors each, plus staggered watches for the two navigators. From 8 to midnight I had my first experience sleeping while underway. The boat was moving slowly enough that once I got used to the sway of the boat, I was able to sleep a little. At midnight it was time for my watch to begin, so I emerged from the cabin below and strapped myself into my harness and attached myself to the jackline in the pitch dark.

Immediately I noticed the stars – so many of them, with Orion rising in the East. It had been mostly cloudy during much of the evening, so I was glad to be greeted with the stars and planets on a night with no moon visible. My first job was to look out for crab pots and lights from other boats. Honestly, even with a small flashlight, seeing crab pots was an almost impossible challenge for my eyes, which were unaccustomed to the dark. We did see other boats as the night wore on – first a Ro-Ro (a roll-on-roll-off car carrier), then a barge with a tugboat, and then a cargo ship. It was wonderfully quiet most of the time, and the crew kept one another awake with gentle conversation. I also steered a little more, but this time I was tasked with steering to the wind. This was difficult, as I didn’t have a good feel for how to keep us in the most efficient course, and I also had trouble reading the navigational equipment from a distance. I didn’t last long, unfortunately. Only the stars, a distant lighthouse, and those few boats kept us company.

Finally it was time to go below to sleep again. This time I slept hard for about two hours but awoke to the sound of movement on deck at about 6am. I stayed below and kept trying to sleep, but the sounds of the boat moving through the water had become louder and more difficult to ignore. The guest cabin was towards the bow of the boat, and every sound was amplified.

When I finally emerged from my berth at 8am, I was surprised to discover that we’d traveled a great distance, as the wind had picked up significantly during the other watch. Amazingly, we were only about 20 miles from the finish and were making excellent time. As coffee was served, someone cried, “dolphin to port!” As it turned out, we saw dozens of dolphins playing as we sped along, frequently jumping completely out of the water and doing flips. The whole crew – even the seasoned sailors – were thrilled with the show.

In what seemed like no time, we reached the latitude of Thimble Shoals, the finish line for the race. We’d long ago left the rest of the boats over the horizon, so we were first to the line. We celebrated with a group selfie and then quickly turned west to motor the rest of the way to Norfolk, just staying to the edge of the shipping channel.

As we motored along, a large US naval ship began to bear down on us from behind, and soon after we saw a submarine being escorted in the other direction. The sub passed quickly. When the ship, the USS San Antonio, passed us, sailors were standing at attention – it was quite the sight. As we drew closer to Norfolk, a C-130 passed close over.

We arrived at the dock in Norfolk at about 12:30. It turned out we were at least six hours ahead of the next boat to arrive. There was little to do but wait for our fellow schooners, nap, and take a shower. The shower was a little adventure in itself – it was in the tiny head. For dinner we had amazing chili, once again cooked by Jen, with guest sous chef Michelle, and of course we had to have Flying Dog’s Numero Uno beer to celebrate. Others hit the bars, and I stayed up with some of the crew talking about music with them, but I was ready for bed by 9, and I slept HARD in my berth for at least 10 hours.

When I finally awoke the next morning, the rest of the schooners had arrived. All of the schooners were docked just a few minutes’ walk from the USS Wisconsin and Nauticus museum, so the guest crew agreed we wanted to visit. We toured the battleship and took a short look around the museum. Then it was time for lunch and the award ceremony. The crew gathered together with the rest of the schooner crews to shuck oysters (I didn’t partake), eat barbeque, and drink beer. Captain Jen insisted the whole crew should go up to the stage to receive our trophies. Woodwind won our boat class, line honors, and the overall race. I was incredibly happy for Jen and the rest of the regular crew. It felt like the ultimate happy ending to a rough couple of pandemic years.

That evening, Jen took me and the other guest crew on a tour of the schooner Virginia, a gorgeous boat based in Norfolk that unfortunately doesn’t get to sail often enough. Beer was served on the Virginia, including beer that had been schlepped from the party in buckets and which was ladled out to the imbibers by members of the Virginia crew. Afterwards the guest crew went to a restaurant for dinner. There was the singing of sea shanties in the awning of the Nauticus museum, and then I went back to the Woodwind for the last night’s sleep. After shooting the breeze with a few members of the crew, I went below and slept once more like a baby.

The next morning the schooner crews gathered for breakfast, and then it was time to say goodbye. I felt that as soon as it had begun, it was all over. It was certainly an adventure to remember.