How do two novice cyclists with almost no overnight trip experience wind up pioneering the TransAmerica Bicycle Trail in 1974? For Jim Richardson and Linda Thorpe, the journey didn’t begin on a grueling mountain pass or in a velodrome. In September 1973, they crossed paths in a Weight Watchers class in Garden Grove, California. After Jim spotted a poster advertising Bikecentennial ’76 in a local bike shop, they decided to swap calorie-counting for a 4,252-mile journey across 11 states on a tandem bicycle. Their 93-day trek was anything but smooth. The couple folded a wheel on railroad tracks, hitchhiked with their tandem to make scheduled TV interviews, and survived mosquito swarms in Montana and Wyoming. Following a terrifying crash in Kentucky, Jim was inspired to propose, and they finally pedaled into Jamestown, Virginia, for a colonial-themed costumed wedding. Jim and Linda’s legendary test ride did more than just help map a historic route for future generations of cyclists—it proved that the road to happily ever after is best traveled on a bicycle built for two, even if it takes 120 flat tires to get there.