St. James 5 Mile Challenge

Lace up for the ultimate test of endurance and scenic beauty at the St. James 5 Mile Challenge, taking place on Saturday, May 9, 2026, in the charming locale of St. James, NY. This highly regarded 5-mile race, often described as a "doozie," offers a demanding yet rewarding course designed to thrill competitive runners. The journey begins with an immediate uphill climb, gradually leveling off before transitioning into three miles of picturesque rolling hills that wind through the historic village of Head of the Harbor. The true iconic hurdle awaits around mile four: the formidable Cordwood Path, a half-mile incline characterized as steep, which demands strategic energy conservation. Runners are ultimately rewarded with a flat and fast finish, ensuring a strong close to this challenging event.

Typical race day conditions in early May promise ideal running weather, with comfortable highs around 67°F and lows near 50°F, accompanied by a minimal 15% chance of precipitation. This event is more than just a race; it's a community celebration with a noble purpose. Proceeds from the St. James 5 Mile Challenge directly benefit Ronald McDonald House Charities New York Metro (RMHC NYM), supporting their $34 million capital campaign to establish a new Ronald McDonald House at Stony Brook Children's. Deepwells Farm serves as the central hub for race-day packet pickup, pre-race announcements, and a vibrant post-race community celebration, with the certified 5-mile course officially kicking off at the bottom of Harbor Hill Road.