The rider seated onboard twin-cylinder Indian racer is Peter H. Cox of New Haven, Connecticut. Standing next to him in all back, racing number pinned to the back of his sweater is Peter’s brother, James F. Cox Jr., and next to him in the white sweater I believe is another New Haven man by the name of George Wildman. The gentlemen racers were all competing, onboard Indians no less, in the Shingle Hill Climb on May 26, 1909. The race, a timed one mile ascent for both automobiles and motorcycles was hosted by the Yale Automobile Club and took place on Shingle Hill in West Haven, Connecticut. The Cox brothers and their club-mate Wildman were also joined by three other competitors including veteran Indian racer William Wray, George Gregory and his FN Four, and G.G. Byrnes onboard an MM. It is quite hard to tell but that is most likely G.G. Byrnes biting his nails in the far back left of the photo, and either Wray or Gregory in the suit just behind Peter Cox.

As usual for 1909 the Indian boys took all of the high honors in front of a crowd of nearly 15,000. Peter blasted up the hill 14 seconds faster than any of the other competitors in the small displacement race, making the climb in 1 minute 4 and 2/5 seconds. He also took the top spot in the free for all event on board the twin cylinder machine seen in this photo, covering the mile in 55 seconds flat. His brother “Jimmy” was never far behind, coming in third place in all three events, a fact I’m sure Peter reminded him of over the following weeks. The sensation of the day however was the veteran William Wray who shot up the hill onboard a similar twin cylinder factory racer in 52 seconds flat winning the twin cylinder race. The long time friend of Indian’s chief engineer Oscar Hedstrom, Wray’s time made all of the headlines as he nearly made the fastest recorded time for any machine that day, two wheels or four. Onboard his 6 HP Indian twin, Wray averaged a speed of 62 mph and was bested by only 4/5th’s of a second by David Bruce Brown in his monstrous 120 HP special construction Benz racer, affectionately referred to as the Automastadon.