In 1873, Webb was serving as captain of the steamship Emerald when he read an account of the failed attempt by J. B. Johnson to swim the English Channel. He became inspired to try himself, and left his job to begin training, first at Lambeth Baths, then in the cold waters of the Thames, the English Channel and Hollingworth Lake.

He is walking from New York to Minneapolis, a distance of 1,446 miles. He expects to make it in 60 day. He is 75 years old and has covered 100.000 miles in long-distance walk in his lifetime. His greatest walk was in 1906, when he hiked clear across the American continent. Upon completion of his present walk Weston will lay the cornerstone of the new clubhouse of the Minneapolis Athletic club.