Strand Gate, Winchelsea – Battery Hill Viewpoint loop from Fairlight

Strand Gate, Winchelsea – Battery Hill Viewpoint loop from Fairlight

Easy

4.2

(30)

riders

Strand Gate, Winchelsea – Battery Hill Viewpoint loop from Fairlight

00:59

19.3km

240m

Road cycling

Easy road ride. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: August 27, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

High Weald National Landscape

Waypoints

Start point

Parking

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8.39 km

Site of Old Winchelsea and Sea Road

Highlight • Historical Site

The line of this road was once the location of the beach - now a few miles away.

This area is thought to be the location of old Winchelsea, which at one time was England's third most important tax revenue in southern England. The sea broke through the shingle bank sometime in 800 AD and provided shelter in the tidal estuary for shipping.

Between 1233 and 1288, strong storms eroded the shingle bank and destroyed the settlement. So, in 1288, a replacement new town of Winchelsea was built on higher ground.

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8.98 km

Strand Gate, Winchelsea

Highlight • Historical Site

Pretty doorway into Winchelsea.

Translated by Google •

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8.99 km

Strand Gate and Lookout View of Rye Bay

Highlight • Monument

This gate is one of the three that once existed in the town. Built in the late 13th century, it provided access to the port.
This gate appears in Thackeray's novel "Denis Duval," which also helps to provide an idea of what life in the village was like in the late 18th century. It is a Grade I listed monument.
In the distance you can spot Camber Castle.

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9.82 km

Winchelsea High Road and Town Gate

Highlight (Segment) • Cycleway

This winding and hilly old access road to and from Winchelsea is characterized by its beautiful views, beautiful old trees and town gate. It is one of the most beautiful roads in the region and a must-see for every cyclist!

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16.3 km

Peter James Lane

Highlight (Segment) • Trail

A winding valley crossing that passes through farm and woodland. It's tougher going south than north. Look out for the caterpillar track-turned-crash barrier on the bend.

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18.0 km

Climb from Pett Level to Fairlight (Hastings Country Park)

Highlight • Trail

18.0 km

View of High Weald from the Beacon

Highlight • Climb

if you travel from Hastings be prepared for a very steep descend.

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18.0 km

Battery Hill Viewpoint

Highlight • Viewpoint

At the turn of the century, a local gun battery from Battery Hill is said to have regularly practiced firing. Fire was aimed at the sea; this was probably the origin of the name "Battery Hill". Centuries before William the Conqueror built a manor house in Fairlight, which he gifted to the French Countess of the EU, her husband was Hastings Castle's first agent.

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