The challenges are part of the annual Hemingway Days festival that commemorates the life and work of the author who lived in Key West throughout the 1930s. The Lazy Dog Paddleboard Race is to kick off at 6 p.m. at the island city’s Southernmost Beach, 1405 Duval St. on the Atlantic Ocean. Competitors are tasked with paddling a 3-mile ocean course before finishing back at the beach. The 5k run is to begin at 7:30 p.m. at the Southernmost Point in the continental United States, located overlooking the ocean at Whitehead and South streets. The fast, flat 3.1-mile course takes runners through picturesque Old Town Key West past landmarks including the Ernest Hemingway Home & Museum. There is a walking division as well.