At the northern base of the hill is the site of Yeavering (known as Ad Gefrin in Bede's Ecclesiastical History of the English People), which was the summer residence of the early Anglo-Saxon kings of Northumbria.

However, by 1107, at the time of the creation of the 1st Baron of Wooler, the settlement was described as "situated in an ill-cultivated country under the influence of vast mountains, from whence it is subject to impetuous rains".

Wooler subsequently enjoyed a period of prosperity and with its expansion it was granted a licence in 1199 to hold a market every Thursday.

Wooler is close to Humbleton Hill, the site of a severe Scottish defeat at the hands of Harry Hotspur in 1402.

This battle is referred to at the beginning of William Shakespeare's play Henry IV, Part 1 – of which Hotspur is the dashing hero.

After the Dissolution of the Monasteries, the patronage and tithe income from the parish church passed from the Bishop of Durham to the Earl of Tankerville.

Wooler also used to have a drill hall that was the local "picture house" which children were evacuated to in World War II.

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