Archaeological discoveries indicate that the area around Helmsley was first settled in around 3,000 BC and small farming communities existed here throughout the Neolithic, Bronze and Iron Ages and into Roman times. Finds of beehive querns confirm local agriculture and the milling of grain since at least the Iron Age. There are also reports of finds of Roman pottery and a second century Roman coin.
The ancient settlement, whose Old English name was Elmeslac, pre-dates the Domesday Book. It means ‘Helm’s forest clearing’ and indicates the nature of the landscape at that time.Vikings also left their mark in the Old Norse, “gate” ending of the names of many of the streets. The ownership of much of the town and its surrounding land has changed hands only twice since the Norman Conquest. After the conquest it was held by William the Conqueror’s half brother the Count of Mortain and land to the west of Helmsley was a royal deer park. The ancient pollarded oak trees in Duncombe Park date from this period and the park is now a national nature reserve. In about 1100 the estate passed to Walter Espec, founder of Rievaulx Abbey. Walter Espec’s heirs were the eldest surviving sons of his three sisters and the Helmsley properties devolved upon Robert De Ros, the son of the youngest sister, Adeline. In 1191 Robert de Ros granted Helmsley its Borough Charter, which established it as the market town.
The charter created the burgage plots — long, narrow plots which can still be seen in the property boundaries on the west side of Castlegate and east side of Bridge Street. Large-scale sheep farming, wool production and weaving were the mainstay of Helmsley’s economy for several centuries. Despite setbacks, including marauding Scots and the Black Death, Helmsley grew steadily throughout the Middle Ages. When wool production declined after thedissolution of Rievaulx Abbey, Helmsley’s weavers turned to flax, much of which was imported. The weavers were located on Bond and Bridge Streets. By the beginning of the 17th century the form of Helmsley was largely complete, and many buildings in use today date from this period. The oldest surviving house is Canon’s Garth, the vicarage. The town remained with the holders of the barony of De Ros through the Earls of Rutland and the Dukes of Buckingham until it was sold to the city financier, Sir Charles Duncombe in about 1689.
The ruined Norman castle is the most significant medieval survival of the buildings in the town, although parts of the parish church and Canon’s Garth are mediaeval in origin. The 18th and 19th centuries saw major developments and expansion in the hands of the Duncombe family, beginning with the construction of Duncombe Park outside the town. At the beginning of the 19th century the cottage weaving industry declined in the face of competition from new industrial cities. Despite this, the 19th century saw various major development in the town, notably the rebuilding of All Saints’ Church, and at the end of the century, building of the town hall. More houses were built along Bondgate and, after the arrival of the railway in 1871, along Station Road. This period also saw older houses remodelled so that little thatch remained in the town. With the decline of weaving, agriculture became the mainstay of the economy.
On 30 June 2011 the BBC2 programme “History Cold Case” featured an archaeological investigation into four two-thousand year-old skeletons found in Windy Pits caves, concluding that at least one had been the victim of a ritual killing, including scalping. The findings, including the facial reconstruction of the scalping victim, were presented, at Duncombe Park, to local history experts.