America’s road racing tradition is rich and varied. From the historic (Boston) to the wild (Bay to Breakers). From hairpin turns (Carlsbad) to beachside hills (Falmouth).
Art of the Road Race celebrates seven iconic races and their most memorable moments, curated below by Toni Reavis.

Each race includes a limited-edition Grayboy and commemorative finisher’s poster. Grayboy Tees and Tanks are available for purchase below. Posters will be hand-stamped and shipped after the race. 



Who knew how fast fast could really be? Though four men’s world records had already been set at Carlsbad, ranging from 13:32 by Steve Scott in 1986 to 13:12 by Kenya’s William Mutwol in 1992, nobody could believe what Kenya’s Sammy Kipketer did in 2000. Going through the opening mile in 3:59, the Kenyan star set a standard of 12:59 in 2000, which he then matched in 2001, also going through the mile in sub-4:00. Nobody has come within ten seconds of Sammy’s record since. Truly, it remains one of road racing’s most legendary records.



In 1995, the Kenyan husband and wife team of Ismael Kirui and Rose Cheruiyot not only won Cherry Blossom, they both set world road records in the process. Ismael ran 45:38, and Rose ran 51:40. They pulled off a similar double that January, winning both divisions at the Belfast International Cross Country meeting in Northern Ireland. Both 10 mile records have since been broken, but it was the only time in Cherry Blossom history that both world 10-mile records were set on the same day, much less by a husband and wife.





1957 champ John “The Younger” Kelley found himself in a three-man tussle with Eino “The Ox” Oksannen of Finland (1959 champ) and Englishman Fred Norris, 39, a former coal miner. Around mid-race a small black dog took up their pace with the runners not giving it a thought. But when a motorcycle cop tried to shoo it away, it darted in among the runners’ legs. Oksannen hurdled out of harm’s way, but Kelley got tripped and went down, skinning his elbow. In an act gentlemanly camaraderie, Norris stopped to help Kelley to his feet, while Oksannen seized the opportunity to break away. Kelley later caught back up, but The Ox used his superior strength to pull away in the spitting snow, winning by 25 seconds. Norris came third another two minutes back. We don’t know what happened to the dog.



At the 75th anniversary of the race in 1986, BYU grad Ed Eyestone became the last American man to win Bay to Breakers. He brought his then girlfriend Lynn Lambert to the race, and set a course record with Lynn watching from the lead vehicle. Then Ed used his first prize, a roundtrip ticket for two to Paris, as a motivation to ask Lynn to marry him, perhaps earlier than he anticipated, because he had to use the tickets before the end of October. They were married October 23rd. Today, Ed and Lynn have six daughters. Thank you, Bay to Breakers.




Five-time women’s champion, and former Boulder resident, Rosa Mota of Portugal twice used Bolder Boulder in late May as a springboard to the Olympic Marathon podium later in the summer. In 1984, Mota won her first Bolder Boulder before taking the bronze medal in Los Angeles at the inaugural women’s Olympic Marathon. Four years later she earned her fourth Bolder Boulder win as a lead-in to grabbing gold at the Olympic Marathon in Seoul. For good measure, she added a fifth Boulder title in 1990 and linked it with another gold medal at the European Championships Marathon in Split, Yugoslavia. Remember when runners used to race as a buildup to their marathons?



While the Peachtree Cup featured a continental-based team competition in 2015, the open division race that followed produced the closest finish in race history. America’s Ben Payne looked to have the title sewn up, but Great Britain’s Scott Overall kept pushing, and when Payne raised his left hand pointing his index finger skyward to signify his win, Overall edged past him by the sheerest of margins. It took race officials over an hour to declare Overall the champion. The winning margin, 9/100ths of a second. Oh, my!


On a brutally humid day, U.S. Olympian Jen Rhines utilized an even-paced effort to become the first American women’s champion at Falmouth since Laura Mykytok in 1994. Early leader and three-time race winner Catherine Ndereba of Kenya pulled off to the side of the road at five miles, cooked. Then Russia’s Olga Romanova, a winner at both Cherry Blossom and Sallie Mae 10K earlier that season, collapsed in the stifling humidity at the top of the last hill, just 200 meters from the tape. Rhines had no idea she had won till race officials told her. World class athletes dropped like ten pins at a bowling alley in the oppressive conditions.



To reserve your hand-stamped poster, submit your email address and select the race you're running. After the race we will send you an email to verify your time, stamp your poster, collect your address, and process payment. Posters shipped to the U.S. are $8 and outside the U.S. are $15.

Fill out my online form.

Join Our Newsletter