The Oakham Canal was opened in 1802. Leaving the old canal basin by the Boat Inn at Melton Mowbray, it followed the valley of the River Eye to Saxby before reaching a wharf which became Station Cottages (the location of the former Whissendine railway station), and then on to Edmondthorpe and Market Overton. Heading south to the Ashwell / Cottesmore Road, it is now crossed by the former mineral railway at the Cottesmore Iron Ore Mines sidings, the site of “Rocks by Rail”, before reaching the Oakham canal basin.

Despite difficulties with water supply, the canal was financially successful, especially in its last 10 years of operation, carrying some 30,000 tons (mainly coal) in 1846. The canal closed in 1847, having been sold to the Midland Railway Company to allow the construction of the Syston and Peterborough railway.

Much of the canal remains in the landscape, with several sections still in water, although the connection with the Melton Mowbray Navigation has been severed. Both canal basins, and the areas east of the Melton Mowbray canal basin and north of the Oakham canal basin, have been redeveloped. Several sections were used for the route of the Syston and Peterborough railway which now crosses the canal at several locations. The site of the former Market Overton wharf, the warehouse (now converted into cottages) and the converted weigh-house can still be seen from the Market Overton to Teigh Road. The former warehouse at the Oakham canal basin is now the Queen Elizabeth Theatre. The stonework around its windows, and the interior beams are the original.