In 1886, Howard Blackburn founded The Old Blackburn Tavern on Main Street, later transformed into the Halibut Point restaurant. Inside, visitors can admire photographs of Captain Blackburn's extraordinary journey and the original cash register. Despite his disabilities from a treacherous voyage at 20, Blackburn continued daring expeditions while running a successful tavern. He became a beloved storyteller, leaving a lasting legacy in the community.

Blackburn Challenge both celebrates and helps to keep alive the story of Howard Blackburn’s desperate mid-winter 1883 rowing of a small fishing dory from the Burgeo Bank fishing grounds to refuge on the south coast of Newfoundland. Though Blackburn survived he ultimately suffered the loss of most of his fingers and toes due to frostbite. In spite of his handicap, he later went on to twice sail solo across the Atlantic Ocean, earning himself the title “The Fingerless Navigator”.

Despite earlier dangers at sea, Howard Blackburn fearlessly embraced a new challenge years later. In 1903, he set out to cross the Atlantic multiple times aboard the Swampscott sailing dory America, only to face obstacles of harsh weather and physical limitations. Yet, Blackburn's indomitable spirit persisted through hardships, including the Prohibition era. Even at 72 years old in 1931, he pondered another solo transatlantic journey, a testament to his unyielding passion for exploration and commitment to the Cruising Club.