On May 23, 1903, Vermont doctor Horatio Nelson Jackson, along with his mechanic Sewall Crocker, drove down San Francisco’s Market Street, hopped on the Oakland ferry, and traveled east into the history books — the first U.S. cross-country road trip was officially underway. This historical moment was born from a $50 wager to see if Jackson could travel from San Francisco to New York in under 90 days. It’s a wager easily won on today’s 164,000 miles of paved highway, but in the early 20th century, most byways west of Nebraska were little more than dirt roads.

The challenge was daunting, but Jackson accepted. He didn’t head due east, which would have sent him straight into California’s unforgiving desert, but instead traveled north into Oregon before making a sharp right turn into Idaho, where he picked up his second passenger — a pit bull named “Bud.” Averaging only 71 miles per day in his Winton touring car on the rough western roads, Jackson also had few reliable maps to navigate his way across Idaho and Wyoming. However, once Jackson, Crocker, and Bud entered Nebraska, paved roads appeared with increasing regularity, and the trio could cover 250 miles in a single day. Yet there were plenty of breakdowns, wrong turns, and other misadventures, and the whole trip took 63 days, 12 hours, and 30 minutes to complete — still well under the original 90-day bet. Jackson was greeted by cheering crowds as the group traveled down the Hudson River in New York toward their final destination. Finally, at 4:30 a.m. on July 26, 1903, the well-worn Winton parked in front of the Holland House hotel in midtown Manhattan. Jackson joyously honked his horn to announce their long-awaited arrival.