Castle to River Run

Castle to River Run takes place in Philipstown, New York, on October 25, 2026. Both formats are run on trail: a half marathon (13.1 miles) at 9:00 a.m. and a 5K at 9:30 a.m.

A trail half is a much bigger day than a road half over the same distance, and treating it like one is the usual mistake. Expect to be out considerably longer, pace by effort rather than by watch, and walk the steep parts without feeling you have failed. In preparation, swap at least one road run a week for trail miles over the final two months and add some hill work, because leg strength matters more here than raw speed. The 5K is the shorter option and a good introduction if you have never raced off-road. Trail shoes are worth the money for either distance.