[1] During childhood Weston moved frequently, and by his own account, spent some time travelling with the popular Hutchinson Family Singers.

[2] He first received attention as a notable pedestrian in 1861, when he walked 478 miles (769 km) from Boston, Massachusetts to Washington, D.C. in 10 days and 10 hours, from February 22 to March 4.

In 1867, Weston walked from Portland, Maine to Chicago, Illinois, covering over 1200 miles (1900 km) in 26 days, winning a prize of $10,000.

In 1874, after several failed attempts, he became the first person in the world to walk 500 miles in six days, accomplished in Newark, New Jersey.

[5] In 1879, he defeated the British champion "Blower" Brown, in a 550-mile (890 km) match which he walked in 141 hours 44 minutes, winning him the prestigious Astley Belt.

In March 1884 he completed his Temperance walk of 5000 miles in 100 days, excluding Sundays, with a meeting at the Royal Victoria Coffee Hall, Lambeth, chaired by Dr Norman Kerr.

[9] Weston was the subject of a 2012 biography, A Man in a Hurry,[10] described by U.S. sports writer Brian Phillips as "a spectacularly entertaining book.