Ermine Street crossed the River Welland on the site of the current town. The Romans established a town at Great Casterton slightly to the north (where Ermine Street crossed the smaller River Gwash) but the Anglo Saxons developed the settlement which has become Stamford itself.

By the 10th century Stamford had become one of 5 controlling boroughs of Danelaw – and by the 13th century it was one of the 10 largest towns in England, with a castle, 14 churches, 2 monastic institutions and 4 friaries. The wool trade was a foundation of its economic prosperity though by the 15th century this was being lost to other centres in East Anglia.

William Cecil, secretary of state to Queen Elizabeth I, was locally born. He built a palatial mansion just outside Stamford for his mother.  Burghley House survives as one of the finest Elizabethan houses in the country.

In the late 17th century Stamford was boosted by improvements to the Great North Road and the construction of the canal to Market Deeping which re-opened the town to river traffic. Prosperous merchants were attracted to the town leaving a legacy of fine Georgian houses. The coaching trade elevated old medieval inns like the George into major nationally renowned hostelries.

Events in the 1960s unusually served to preserve the historical centre of the town. In 1960 a bypass opened to carry the A1 west of the town. Then a few years later Stamford was the first conservation area to be designated under the Civic Amenities Act 1967.

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