The Mediterranean region is experiencing unrelenting land-use pressure, largely driven by population growth. Long-term cropping system trials can guide crop and soil management options that are biophysically and economically sustainable. Thus, an extensive cereal-based rotation trial (1983–98) was established in northern Syria, to assess various two-course rotations with durum wheat (Triticum turgidum Desf.). The alternative rotations were: continuous wheat, fallow, chickpea (Cicer arietinum), lentil (Lens culinaris), medic (Medicago spp.), vetch (Vicia sativa) and watermelon (Citrullus vulgaris) as a summer crop. Ancillary treatments were: nitrogen (N) fertilizer application to the cereal phase (0, 30, 60 and 90 kg N/ha) and variable stubble grazing management (zero or stubble retention, moderate and heavy grazing). Both phases of the rotation trial occurred each year. The soil is a fine clay, thermic Calcixerollic Xerochrept. Seasonal rainfall was the dominant factor in influencing overall yields. Rotations significantly influenced yields, being highest for fallow (2·43 t/ha), followed by watermelon (similar to fallow), vetch, lentil, medic and chickpea, and least for continuous wheat (1·08 t/ha). Overall, yields increased consistently with added N, but responses varied with the rotation. The various stubble grazing regimes had little or no effect on either grain or straw yields. While the trial confirmed the value of fallow and the drawbacks of continuous cereal cropping, it also showed that replacing either practice with chickpea or lentil, or vetch for animal feed, was potentially a viable option. Given favourable economics, legume-based rotations for food and forage could contribute to sustainable cropping throughout the Mediterranean region.