Trail Running calendar near Winchester 2026-2027

We have found 126 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

A minimally marked 40.3-mile counter-clockwise loop through the Massanutten Mountains with about 6,500 feet of climb, three aid stations, and limited entry; participants must self-navigate, self-support, and prepare for winter mountain cond..

January 2027

A 50 km New Year trail run at Prince William Forest Park with three repeats of a roughly 10-mile loop, mostly on groomed trails. The event uses an unmanned aid spread at the start/finish and has limited entry.

A 32 mile point to point mountain training run on Jan 16, 2027, covering roughly the first third of the MMT 100 with about 4,600 feet of ascent. It requires a shuttle, includes two aid stations and has limited entry.

February 2027

A 50 km trail run at Hashawha Environmental Center near Westminster MD featuring 31 miles of mixed surfaces, 5,800 feet of elevation gain, five aid stations and a 9 hour time limit. Lottery entry opens Jan 1, 2027 for ten days.

March 2027

A rocky, technical 50 km on mostly forested single track in the northern Massanutten range, with 6,400 ft of elevation and limited aid at Mudhole Gap and Elizabeth Furnace; navigation relies on blazes, turnsheet, and GPX.