Flint hand axes found deep within glacial gravel at Welton le Wold show that early humans were living in the Lincolnshire Wolds over 300,000 years ago. Isolated pieces of stone tools turned up by the plough are typical of the evidence for hunter-gather peoples living in the Wolds between 10,000 and 6,000 years ago.
The Lincolnshire Wolds has many Neolithic long barrows, communal graves in which the bones of the dead were deposited over several centuries. Often these barrows were also ways of marking land ownership – important for the first farmers. Round barrows, the distinctive burial mounds of the Bronze Age around 2000 BC, can still be seen throughout the Lincolnshire Wolds.
The Romans recognised the farming potential of the Lincolnshire Wolds and established major settlements at Horncastle, Caistor and Ulceby as well as a network of smaller settlements and villas. Some of these villas were built by soldiers who, upon retirement, were give an allotment of land.
Many Roman roads crossing the Lincolnshire Wolds are still in use today. Caistor High Street between Horncastle and Caistor is one of these. A major Roman route once connected Lincoln to a long since eroded port near Ingoldmells and then onto salt making sites along the coast.