To inform a proposed planning application, a trial trench archaeological evaluation was undertaken on land at Highfields School, Newark. The site comprises four enclosed areas of sports or playing fields. Although the archaeological potential of the site was previously unknown, Newark has a rich and varied history, ranging from the Bronze Age through the Roman and Saxon periods when the riverside settlement expanded. Aerial photographs of the area have revealed cropmarks and earthworks indicating activity on the periphery of the settlement, extending around the proposed development site. The medieval town thrived on the trade of wool and cloth; the river being utilised to transport goods around the country. Newark was a strategic stronghold during the Civil War; a Royalist stronghold that came under siege repeatedly, finally surrendering when the king was captured in 1647. The military earthwork fortifications are still visible in the area, with Crawfords Sconce, a Parliamentarysiege position, lying c.350m southwest of Highfields School. Highfields House was built in the mid 19th century, later converted to use as a school. Fourteen trenches were excavated to investigate anomalies identified by a preceding geophysical survey. A complex of ditches and occasional pits were revealed to the north and east of the school buildings. Dating evidence indicates small scale activity in the Iron Age and Roman periods associated with an enclosure to the north of the school, and medieval and post-medieval agricultural activity.