Starting from the Wye Bridge in Monmouth, the Wysis Way heads eastwards up The Kymin and into the Forest of Dean. Heading primarily eastwards, the trail goes through Hillersland before continuing through the Forest, passing through Nailsbridge, Harrow Hill and Mitcheldean on its way to the top of May Hill () and views of the River Severn. From May Hill, it continues eastward through Glasshouse, Taynton, Tibberton and the edge of Highnam before reaching Gloucester. At Gloucester, the trail starts to head more southerly but still in an eastern direction up to the trig point on Robinswood Hill () before continuing southeasterly through Painswick, Bisley and Oakridge Lynch where it turns east along the River Frome and the Thames and Severn Canal to Daneway and Sapperton, Gloucestershire before reaching its end in Kemble, where it meets the Thames Path.