This walk leaves Heathfield via Sandy cross and then continues across fields to the village of Old Heathfield, (the original town). Passing through the Churchyard the walk continues to Cade Street. Cade Street gets its name from Jack Cade who, in 1450 led an army of insurgents to London. Just off the route along the main road is a monument where he was killed by the Sheriff of Kent. From Cade Street the route continues across fields with good views across the High Weald.
Rushlake Green has a shop and a pub, and at the heart of the village is the village green. After leaving Rushlake Green the remains of the iron industry can be seen. The river has a rusty tint from the deposits of iron. The walk continues over the rolling hills of the High Weald, passing through Nettlesworth Wood which is spectacular when the bluebells are in flower. The fields after Nettlesworth Wood are full of wild flowers in the summer. The walk continues through the SSSI of Sapperton meadows before joining an old railway line, the Cuckoo Trail.