Roxbury Fall Classic

Roxbury Fall Classic is run in Roxbury, Connecticut, on November 14, 2026, in the state's Northwest Hills. The 50K (about 31 miles) starts at 7:30 a.m., with the marathon (26.2 miles) and the half marathon (13.1 miles) following at 8:30. Courses are hilly and mix paved surfaces with dirt roads and trails, and a cutoff time applies.

That surface mix is what you should train for. Long runs on pavement alone will leave you unprepared for the footing, so build some of your weekly distance on dirt and hills, and get comfortable walking the steepest climbs to save your legs for later. The longer races run loops, and there is an out-and-back stretch along Judds Bridge. Check the cutoff against a realistic estimate of your finishing time before entering, particularly for the 50K, which is the step up from a marathon rather than a variation on it.