The Phatwater Challenge ain’t your average kayak marathon. One former winner of the fall, 42-mile race down the Mississippi River, three-time Olympian Mike Herbert, once wrestled a 725-pound black bear to win a car. The Natchez, Miss., race headquarters is a bluesy biker bar, the Under-the-Hill Saloon, decorated with crawfish pots, tortoise shells and faded paintings of prostitutes and manned by a 4-foot-11 bartender who can pluck a lit cigarette out of the air with chopsticks. (Hang out long enough and you’ll meet a chicken named Pretzel who eats peanuts off the bar.) And before native son, Keith Benoist, a silver-haired 55-year-old ex-Marine, moved back to Natchez in 2001, racing kayaks on this stretch of the river was less common than UFO sightings.

In 2002, Benoist paddled from Grand Gulf, the first viable put-in upriver on the Mississippi side, to the boat ramp below the Under-the-Hill Saloon, which is owned by his girlfriend and her brother. That solo trip spawned the first Phatwater Challenge, with all of 11 entrants, seven months later. In 2007, the first year he offered prize money—$1,000 to the first male and female finishers and another grand for the first paddler to crack four hours—99 paddlers showed up.

“My goal,” said Benoist, in a voice that somehow sounds both harried and mellow, “is to create the preeminent downriver kayak race in the country, a race that serious paddlers cannot afford to ignore.”

I heard about the race from two world-class South African paddlers who competed in 2008, calling it brutally long but delightfully quirky. Having now done the race twice, I can concur. Part of the appeal is Natchez itself, where history is tied to the waterway the Ojibwa Indians called misi-ziibi or “Great River.” The Spanish explorer Hernando de Soto passed through the area in 1540 but things didn’t really get going until the French arrived in 1716 and built a fort on the bluffs above the river to protect their trading interests. New Orleans wasn’t even in diapers yet. Natchez was the first settlement on the Mississippi and, for a time, the richest. At the start of the Civil War, there were more millionaires in town than anywhere else save for New York City.

But Natchez had its seamy side as well, and back in the 1800s the Under-the-Hill saloon was at the heart of it. “It’s been a brothel, warehouse, grocery, general store and probably a few other things,” Benoist said. Sitting on the porch with a beer in hand, watching the sun set on the Louisiana side, it was easy to picture men streaming up the hill from their boats on the river in search of whiskey, illicit love, and a game of five-card stud. Law enforcement was lax to the point of nonexistent. Some saloons, built on stilts over the river, had trapdoors to allow easy disposal of the bodies of travelers who were clubbed to death and robbed. Even more unsavory, Natchez was the site of the second-largest slave market in the South, a fact I learned from a burly black man named Clifford Boxley that I bumped into in town. Boxley, a dedicated historian, was dressed in a full Union Army uniform at the time.

And then there was the kayak race. On October 9, 165 paddlers gathered in the dawn’s early light for the start at Grand Gulf, a key supply point for Grant’s army during the siege of Vicksburg. I saw two masked men in red capes and blue briefs over red tights in a black carbon canoe; they called themselves Los Humongos Paddlelos. Less frivolous and far faster was the solo winner Sean Lupton-Smith, a South African living Newport Beach, Calif., who finished in 4 hours, 1 minute. Posting the fastest time of the day was the husband-and-wife duo of (and fellow South Africa-rooted, Southern California residents) Patrick and DeAnne Hemmens, with a time of 3:54.

Benoist seems well on his way to creating a race that serious paddlers can’t afford to ignore. But during the post-race bash, a woman and her dog were dancing at the bar as the band did a killer rendition of Janis Joplin’s “Piece of My Heart,” and … well, I found myself wishing that the non-serious paddler would keep showing up as well. — Joe Glickman

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