Glenwood takes part in the inter-schools cross country league where eight league meetings take place during the Second Term and Third Term. Venues include Hutchinson Park in Amanzimtoti), Curro in Hillcrest, Virginia Bush, Kearsney, Crawford College (Umhlanga), Gate 10 UKZN and Umhlanga College. On average 20 boys have been competing on a weekly basis.
Cross country boys also participate in the tours to Grey College (Bloemfontein), Monument (Krugersdorp), Affies (Pretoria) and Framesby (Port Elizabeth). We have also become the first school to regularly attend trail running events and have run at the Giba Gorge, Scottburgh (Rocky Bay), and the night event at Hilton.