When writer Ernest Hemingway first fell in love with Key West in 1928, the small Florida island scarcely resembled the busy tourist lined city of today. Closer to Cuba then to mainland Florida, the island was more accessible by boat than car until the Overseas Highway (now U.S. Highway 1) was finally completed in 1938. Hemingway found the secluded tropical island to be an ideal place for big game sport fishing, boating and writing. He would go on to write several of his best selling novels including For Whom the Bell Tolls and To Have and Have Not from his coral-stone house in what is now referred to as Old Town Key West.

While things have changed substantially on the island, we could still see remnants of the city’s rich history on nearly every street corner. From the historic taverns still operating, to the palm-lined streets bordered by quaint tin roofed conch houses, Key West still has the feel of an old port town. We had come to the Florida Keys in the middle of July. And although here in the Midwest, we tend to arrange our trips to the tropics during the frigid winters, we braved the tropical heat for the best scuba diving season, Ernest Hemmingway Days, and the Key West 5K Sunset Run organized by the Florida Southernmost Runners Club.

The run was unlike any I’d attended. Its timing to coincide with the Hemingway Days festival provided us with plenty of entertainment, both before and after the race. Walking down Duvall Street on our way to the starting line near the southernmost point of the continental United States, we were treated to countless bearded contestants from the Hemingway look alike contest bellying up to the street vendors for a shrimp kabob or a piece of fresh grouper. We arrived at the starting point half an hour before race time to find runners packed into the narrow street drinking water, stretching calves and hamstrings against palm trees, and hoping to catch the elusive evening trade breezes that would bring at least a temporary reprieve from the heat.

As the sun slipped towards the horizon, smearing the western sky with its red-orange hue, we took our place for the flat 5K course. The route would take us through the neighborhoods of Old Town Key West, past the lush grounds surrounding Ernest Hemingway’s house, and out onto the pier for the turn around point.

The starting gun fired at 7:30 p.m. and the runners spread out quickly among cheers from other runners, friends, and the locals, who had come down to see what all the excitement was about. We were all watching favored runner Ronnie Holassie as he shot away from the starting line. Unfortunately, he was having hamstring problems during his warm up and had to stop 100 yards into the race and stretch. It will probably be the only time we would pass a runner of his caliber during a race. Our small victory would not last long however, as Holassie reentered the race after stretching, and passed all the 270-plus runners to finish first with a time of 16:34 just 10 seconds ahead of Don Wennerstrom. Holassie, who is training for a marathon this fall and is a U.S. Olympic hopeful, later good-naturedly commented that, “It’s been a long time since I ran a 16-thirty something. I do training runs faster than that. I was still happy to win. I decided just to run for the win instead of trying to hurt myself more. I’m very cautious with what I’m doing right now.”.

The flat fast course itself offered little difficulty in terms of topography. The real challenge, especially for those of us from the north, was the heat. Race day temperatures soared into the 90’s but all the runners, ranging in age from 11 to 73 seemed prepared and finished the race carried by cheers of encouragement from the others. After the race was finished, many of us walked down the street to pose for our post-race pictures in front of the monument designating the southernmost point of the continental United States, just 90 miles from Cuba.

As the sun dipped below the water and the temperatures cooled, we all congregated around the pool at the Southernmost Hotel to exchange stories, cool off, attend a raffle for prizes donated by local vendors, and talk about upcoming races. Then it was off to Duvall Street again, where we spent the rest of the evening. Wandering through the waves of people still partying at the Hemingway Days festival, we took in the smells of fresh grilled fish, and the sounds of local bands drifting invitingly out onto the street. As the evening wound down, we made our way back to the car, greeting runners who hadn’t yet removed their numbers, and looking forward to our next visit to the island that Hemingway called home.