Editor’s note: Read the article on this award-winning short story here.

“Up from the meadows rich with corn, clear in the cool September morn, the clustered spires of Frederick stand, green walled by the hills of Maryland.” My grandfather muttered this as the race horn sounded. Weaving in and out of boats, he skillfully drew the tiller back and forth to avoid a collision, a look of happiness and determination on his tanned, wrinkled face.

Sailing with my grandfather, surrounded by dinghies on this warm August Saturday, made me feel happy and safe. I was the first person he asked when he needed crew to race with him in his sailboat “Moby Dick.” The starting area was filled with a large fleet of dinghies, gathered for the weekly race. The small, one-sail boats were closely packed together as the horn announced one minute. His eyes gleamed as he spoke the last verses of the Barbara Frietchie poem, which took him exactly five minutes to recite. He said it at the start of every race, instead of using a watch, to know exactly the amount of time before the starting horn.

“Peace and order and beauty draw; Starboard! Starboard!” he cried, while positioning his boat on the line. I always stifled a laugh when he recited the “peace and order” verse during the start, the most stressful time in the race. “Round thy symbol of light and law; quick pull in the sail!” he shouted at me from the side of the boat. I rushed to grab the mainsheet as the five short beeps followed by a long beep, signifying the start, blared from the Race Committee Boat.

“Hike, hike,” he told me as we turned up into the wind. I felt the cool, ocean droplets sprinkle on my face, the sun warm on my shoulders. We had a great start. Starboard, right by the committee boat, and we were covering, or blocking the wind of, about half the fleet.

“Great day for a race,” Chad Worthington, my grandfather’s ongoing rival, shouted from another boat. Suddenly, Mr. Worthington pushed the tiller away from him and headed us up into the wind, missing us by an inch. He was fooling around, attempting to get his stiffest competition disqualified. A sneaky smile spread across his craggy face.

My grandfather’s eyes narrowed. “Don’t get into arguments on the water, Abigail. It’ll just put you in last,” he told me.

We sailed along peacefully, the sound of the waves hitting the front of the boat. The warm sun on my face made me slightly sleepy on this light air day.

Suddenly, I was jolted from my lazy daydream by a deep voice, “Tacking!” my grandfather cried, as he pushed the tiller away and switched sides of the boat. I quickly hopped over and hung my torso over the opposite edge. The whole fleet copied his every move, cries of leeward and starboard filled the air as boats fought for right of way. Grinning wildly, my grandfather yelled loudly that we were tacking again, and all the boats followed us. He had the fleet in his hand. Laughing to himself, I guessed that he already knew we were going to win this race.

A lieutenant in World War II, my grandfather was a leader. When he raced, he either would come in first by a mile or last by a mile. He never followed other skippers and always sailed his own course. He wanted to win, but when he lost, he just laughed. He seemed so carefree, yet he was careful. I was never scared to sail with him as I knew we would be okay. I had gone out with him on the most blustery days, when whitecaps filled the thoroughfare. He knew the tides like the back of his hand, and he could easily draw a map of all the dangerous rocks hidden in the channel. Before every race he would tinker with the boat, switching the ballast, tightening the sail, or just switching things up. He was full of imagination, and just wanted to enjoy himself on the water. Unlike Mr. Worthington, whose biggest interest was to collect half-heartily won sailing trophies to display in the center of his house.

“Abigail, do you see any storm clouds?” he asked, looking sincere. I almost laughed. This was the clearest, calmest day.

“Of course not. It is so flat out here. I am surprised we are moving,” I answered respectfully.

“Hmm…” he grunted under his breath. I wasn’t old enough to understand how quickly conditions can change.

I did know the hardest part was yet to come: The Dumplings, the little islands my grandfather insisted on sailing between on light air days. This was the active time for the crew; pull up the centerboard, hike, and watch for rocks, all at once. It would be solitary though because no one would dare to follow us into the collection of ledges that had shipwrecked so many before. But he could do it.

We weaved in and out of the seaweed-covered rocks, a sign of low tide. The current was weak, so we moved along nicely. I peered over the gunnel, looking at the ocean bottom, faintly seeing the crabs scurrying for cover, afraid of the shadows the boat created.

“Get ready, Abigail! The lee will be gone soon,” said my grandfather, his eyes darting around, examining the wind, current and rocks up ahead. Suddenly, almost just as he said it, the wind picked up, like a switch turned on. Rejoined with the crowd of dinghies, we found ourselves in the middle of the fleet.

“Huh, I guess the wind was better out here,” he said, surprised his usual technique for light air days didn’t work. Mr. Worthington, leading the pack, eyed our boat. “Not this time, Perry,” he shouted over the water. “This race is mine!”

My grandfather shook him off and held his course toward the first mark, the metal buoy clanging in the distance. The sky had darkened and the water turned an icy gray. It still looked sunny in the opposite direction, but in less than five minutes the harbor was filled with menacing clouds. It was clear a squall was coming. My stomach sank with a nervous feeling as it always does when the wind picks up and the sky shifts. My grandfather and I were both calculating the amount of wind that would hit us once we sailed into open water, no longer protected by the small thoroughfare. I sat on the edge of the boat, biting my nails, in an anxious daze.

“Abigail, stop biting those nails, they’ll be nothing left,” he said hurriedly. His tone scared me. He was serious. A switch hadn’t only gone off with the wind, with my grandfather as well. I stopped biting my nails, but my stomach remained queasy. We were on a clear course for the first mark, but covered by another boat. My grandfather skillfully pushed the wooden tiller away from him, forcing the other boat up into the wind. We passed them and many others, ducking and pointing until we rounded the first mark in fourth place. Mr. Worthington looked back at us. Using the heavy wind to our advantage, we quickly passed ten boats, the other skippers nervously pointing their bows into the wind and letting out their sail too much to avoid the dreaded capsize. We were cruising. My stomach burned from hiking out to balance the boat, but we were going fast. However, we were still a considerable distance from first place.

I saw them first. Coming like an army over the horizon. At least fifty of them, in a long parade, stretched out on the ocean.

“Granddaddy,” I whispered to avoid other skippers from hearing my ignorance. “What are those?”

“Ah, the New York Yacht Club, making its way up the Maine coast. We’ve got to play this right, Abigail. It could put us in first. In order to complete the race we have to cross the channel twice,” he lectured, glancing around. He seemed familiar with this scene.

I looked around too, pretending to be thinking about something important, but really I couldn’t take my eyes off the enormous yachts coming up behind us; large wooden masts, several stories high and hulls that stretched fifty feet. All of them had exotic flags on the stern, proudly displaying their origin. Some of the other racers had spotted them, and I could hear them strategizing about how to navigate through the fleet.

“We are heading up, Abigail,” my grandfather shouted over the strengthened wind. I leaned out, my body parallel with the water, hands over my head. It seemed we were cutting across the thoroughfare at a strange angle. Instead of going to the mark on a broad reach, like you’re supposed to, we were heading up almost into the wind. We were moving faster, but not closer to the mark. Other racers stared at us, their faces revealing that we had finally lost our minds. We continued on and crossed the channel in no time. We then headed dead downwind on a course toward the mark. It took longer, but we started to see our competition slow down as the New York Yacht Club approached. The huge sails were stealing all the wind, and most of the boats were in the lee. Some NYYC boats honked, trying to get the racers to move out of the way. It became a mess of sails and hulls. My eardrums shook as I watched the furor in the distance.

Amazingly, we were now in the lead and I could calmly sit back to watch this all play out. But even my grandfather, always focused, seemed distracted by the craziness with the boats. We both heard a sharp crack and our attention was back in our boat. Our bow slowly began to fill with a steady trickling of water. I could see my grandfather tense up.

“Damn it! Abigail, grab that rag and push it against the hole! Grab the bailer, too,” his voice urgent. Under his breath I heard him pray that he remembered a hole patch, kind of funny, considering he wasn’t very religious. I only heard him mention God on the water. Soon as he said it, I jumped toward the bow. I pumped the water, but the leak was definitely slowing us down. Other boats had made it out of the NYYC mess. We were getting closer to the mark, when my grandfather motioned to me to take the tiller. A rush of nervous adrenaline went through me. I had only sailed “Moby Dick” when we were cruising around in light air. Never in a race, and never during “a situation.” I was always the crew. My grandfather looked at me with pleading eyes and I dropped my rag and bailer, nervous to take his spot as the captain.

The moment I touched the splintery wood the fear washed away and I wondered what I had been doing, wasting my time as a crew. A skipper is where the magic is. I knew what to do from watching my grandfather, but I had never been in charge. I had never had the choice of going exactly where I wanted, of being the leader. My grandfather occasionally called out warnings: “Watch the gust here; do you see that boat covering us?” But it was mostly me; I was the skipper now. The other dinghies were gaining on us, and I felt the frustration of sailing a leaky boat.

We rounded the mark, wide and tight, followed by Mr. Worthington trying to disqualify us. “Buoy room! Buoy room, Perry! I’ll protest you unless you do your spins,” he shrieked. A skipper and crew in another boat rolled their eyes. No one was a fan of his fallacious antics.

“Wait, Perry,” Mr. Worthington said, “Are you really letting your granddaughter sail this race?!” He laughed with wicked delight. I kept my eyes straight ahead and focused on the course toward mark number three, almost parallel to number two. “You must be getting too old, Perry!”

I saw my grandfather frown, knowing perfectly well that he was the one who was the more capable sailor. Yet he said nothing. I kept steering, moving around the thoroughfare for the best wind, which had quieted down once we came back into the channel. Mr. Worthington followed us like a shadow.

The hole was plugged, the squall had passed, the New York Yacht Club had drifted away and first place was mine. We were coming up on the cove entrance, on a beam reach. Without warning, the boat quickly keeled over, my grandfather’s left arm was in the water and I was fighting with the tiller for control. He jumped to the other side of the boat, yelling to let out the sail. I screamed as I attempted to un-cleat the main sail. In the panic of trying to get the line loose, I let go of the tiller. We whipped around up into the wind and collided into Mr. Worthington. I had T-boned the enemy. I was trembling when I finally looked up at what had happened. Feet away from the finish line, I put us out of control. My grandfather had always warned me about strong gusts blowing from the cove, even he had capsized there once, but today he didn’t mention it. Everyone on the water saw what had happened. I even saw a few leading NYYC boats pull out their binoculars, watching like cars passing a crash on the highway. Mr. Worthington screamed, “Told you your granddaughter couldn’t do anything.” He didn’t seem angry that we had put a dent in his boat, but pleased that he would win this race because of my error. I wanted to shout back at him and defend myself. Tell him he was a jerk who didn’t deserve first place. As I opened my mouth, I caught a death stare from my grandfather. His eyes pierced through me. I felt so ashamed.

We placed third. I thought my grandfather was mad at me for losing, especially to Mr. Worthington. When Mr. Worthington accepted his award at the tea he announced,

“I’d like to thank my crew for helping me. Also, there is one other person who I couldn’t have won this race without. Thank God for her bad sailing!” he said laughing. We left then. I couldn’t bear to look at someone that horrible. When we returned home, my grandfather simply said I had learned a lot on the water, and there would be plenty of other races.

* * *

The beautiful blue of the ocean water has stayed the same these past 30 years. The Race Committee still runs the same race course as the one I used to sail with my grandfather. Even the people stay the same. Last year, I beat old Mr. Worthington’s grandson, Brooks Worthington, in the July Series. He cursed and stormed out of the room when they announced it.

“Mom! Do you see him?” shrieked my eleven-year-old daughter, pointing to a boat on starboard heading directly toward us. A daydreaming skipper! My grandfather would not approve. “Abigail, if you are not focused you will not win this race,” I could hear him in my head. I moved the same old splintery tiller away from me and shouted “tacking!” for the whole fleet to hear. My daughter laughed when she saw the boats follow our every move. I laughed with her and told her about the importance of taking risks and going your own way. She took it as a sailing tip, like I did when I was eleven. Now I know my grandfather wasn’t teaching me only about sailing. He taught me more about how to behave in life in that one race than in any class or book. If he had just wanted to win that day, like Mr. Worthington, he could have held onto the tiller, or warned me about the predictable gusts coming from the cove. But he knew, at some point, I needed to figure it out myself.

We came upon The Dumplings, sailing through the passageways between the tiny islands. “Let’s go over there! Look at the gusts!” shouted my daughter.

“We can’t, Madeline, there’re rocks,” I told her. “Plus the current’s stronger.” She looked at me in awe, impressed that her mother knew these hidden dangers so well. “You can’t go through The Dumplings unprepared, Abigail,” he would say to me.

We emerged from The Dumplings and back into the fleet, to find ourselves in first place. “Ha-ha! Let’s turn around and stick our tongues out at Brooks Worthington!” pleaded my daughter.

“No, Madeline, you sit down right now,” I scolded. “We never insult people in the race. Do you want to be like the Worthingtons? You must win and lose with grace and sportsmanship.” I imagined my grandfather smiling as I passed these lessons on to Madeline.

“Do you think there will be a squall today?” I asked Madeline sincerely. She laughed at my suggestion.

“No way! Are you crazy?” We both laughed.

Coming around the first mark, wide and tight, I turned back to see our competition still working to get past the little islands. We were lazily sailing for a while when out of the blue she asked, “Hey, Mom, can I steer?”

I passed her the tiller and a smile spread across my face. “Chart your own course,” I heard my grandfather say, as the first drop of rain hit the splintery tiller.