SummaryAlthough the Shephelah region (Israel) is of a great archaeological significance and has been intensively excavated, very little is known about its landscape history. This study presents two large‐scale charred wood assemblages (>2300 items) that were recovered from Tel Azekah and Tel Lachish in order to reconstruct the ancient vegetation of the Shephelah. The two assemblages cover a temporal range from the Middle Bronze Age through the Hellenistic period (c.2000–100 BC). This new diachronic environmental investigation demonstrates that the natural arboreal vegetation in the Shephelah was dominated by oak and pistachio. From the perspective of the regional fruit tree horticulture, olive was the dominant component, indicating that the region included extensive olive orchards. Other documented fruit trees are grapevine, fig, sycamore fig, carob, date palm and almond. The high frequencies of olive remains throughout all investigated periods point to climatic conditions in the region being close to what we are facing today, with at least 400–450 mm of annual precipitation, which is required for a profitable grove. During the Iron Age II, the proportion of olive remains reached its zenith, most probably as a result of Assyrian agroeconomic management that assigned the Shephelah to olive oil production. At the same time, a reduction in natural Mediterranean trees was identified, representing intense human pressure on the natural environment. The discovery of charred cedar of Lebanon remains only at Lachish points to the high status of the site within the region.