The £4,000 project was funded through Yorkshire Forward's Renaissance Market Town programme, supported by Harrogate Borough Council and Boroughbridge Town Council. The route is one of six walking trails developed as the Ure Walks Through Time project.
The oaks, from Barcham Trees and planted by Skeltons of High Birstwith, are in 250-litre grow-bags. Harrogate Borough Council assistant arboricultural manager Alan Gilleard said the trees will quickly root down into the ground once the bags are removed.
"We hope that children and residents will get enjoyment from watching these trees grow and mature for many generations to come," he said.