Marathon races near New Windsor

The Tarrywile Half Marathon is a November trail race held in Tarrywile Park, Danbury, Connecticut, featuring exclusively unpaved park trails. The event includes a 10K, half marathon, and marathon, all utilizing a consistent hard loop structure: one loop for the 10K, two for the half, and four for the marathon. This course is not a road race with some dirt; it consists of Northeast single track, rocky and rooty sections, and sufficient climbing to significantly slow runners compared to their typical road pace. The 10K involves approximately 1,500 feet of climbing, the half marathon around 3,000 feet, and the marathon reaches about 6,000 feet of elevation gain. Participants gain viewpoints over Danbury and the park's lakes, though these require navigating technical, hilly trails. Hikers and walkers are permitted in the 10K and half marathon provided they can finish within the seven-hour time limit. The event maintains a small scale with a 250-person limit. The half marathon also features a standing cash challenge: bonuses are awarded to the first man finishing under 1:45 and the first woman under 2:00, with the prize pool increasing annually until claimed.

The Millbrook Marathon is a 26.2-mile road race in Millbrook, New York, presented by the Eastern Dutchess Road Runners Club. It takes place in April, starting promptly at 7:30 a.m. from the Town of Washington Park and Pool on Route 44, with a six-hour time limit. The course is USATF certified and eligible as a Boston Marathon qualifier, attracting runners seeking an official marathon time over a casual event. The route follows Millbrook roads, featuring rolling hills, primarily pavement with some packed dirt sections, and approximately 2,400 feet of elevation gain, making it unsuitable for those seeking a purely speed-focused race. The setting is rural Dutchess County, with quiet country roads and farms highlighted by organizers as key attractions. Awards are presented to the overall male and female finishers and to winners in each age group, while the first 200 participants are guaranteed finisher medals. Club members receive a discount, and early registrants are assured a race T-shirt.