The route begins at Lewes Station and follows the steady incline eastward toward the golf course. Lewes occupies a strategic position above the River Ouse, and its name is generally understood to derive from Old English hlēw or hlæw, meaning “hill” or “mound,” a reference to the prominent chalk heights on which the town sits.

At the top of the hill, the path crosses Lewes Golf Club, established in 1896 on the chalk ridge. Walking across the fairways requires attention, as golf balls can land without much warning.

Continuing east, the route passes the Cuilfail Monument, a modern sculpture installed in 1993. The name Cuilfail is believed to come from Old English elements meaning “nook” or “corner” combined with “fold” or “enclosure,” reflecting the shape of the valley at this point.

Beyond this, the path skirts Cliffe Hill, whose name comes from Old English clif, meaning a steep slope or escarpment — an accurate description of the chalk face overlooking the eastern side of Lewes.

The walk then continues toward Week Lane. “Week” is a common Sussex place‑name element derived from Old English wic, meaning a dairy farm or settlement. From here the route rises to Saxon Down, an area containing several tumuli. These burial mounds are typically Bronze Age in date and indicate long-term human activity on the ridge.

The return follows the road from the golf club back into Lewes. Conditions on the day were cold, around 1°C, but visibility was clear, providing unobstructed views across the Downs.