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Monks Walk Ruins – Strand Gate, Winchelsea loop from Winchelsea

Monks Walk Ruins – Strand Gate, Winchelsea loop from Winchelsea

Easy

riders

Monks Walk Ruins – Strand Gate, Winchelsea loop from Winchelsea

00:43

14.3km

140m

Road cycling

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: May 27, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

High Weald National Landscape

Waypoints

Start point

Bus stop

Get Directions

488 m

Monks Walk Ruins

Highlight • Historical Site

552 m

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!

Translated by Google •

Tip by

8.93 km

The Red Pod

Highlight • Cafe

Stop here for a tasty hot dog, tea, coffee or cake. All locally sourced and vegan/veggie options are available. Open 10am to 4pm at the weekend.

Tip by

13.3 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.

Tip by

13.9 km

Strand Gate, Winchelsea

Highlight • Historical Site

Pretty doorway into Winchelsea.

Translated by Google •

Tip by

13.9 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.

Tip by

14.2 km

St Thomas the Martyr Church, Winchelsea

Highlight • Religious Site

Now partly in ruins, the 13th century St Thomas the Martyr Church is dedicated to Thomas Beckett, Archbishop of Canterbury. The church was built when the whole village of Winchelsea was moved inland and uphill after flooding decimated the port of the same name. There are differing accounts as to whether the building was ever finished or if it was partly destroyed in an attack by the French. It is worth looking inside at the intricate masonry, medieval tombs and early 20th century stained glass window.

Tip by

14.3 km

End point

Bus stop

Way Types & Surfaces

Way Types

13.9 km

172 m

156 m

< 100 m

Surfaces

8.93 km

5.17 km

172 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (50 m)

Lowest point (0 m)

Weather

Monday 13 July

29°C

16°C

0 %

Additional weather tips

Max wind speed: 24.0 km/h

to get more detailed weather forecasts along your route

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Monks Walk Ruins – Strand Gate, Winchelsea loop from Winchelsea

Monks Walk Ruins

Winchelsea High Road and Town Gate

The Red Pod

Site of Old Winchelsea and Sea Road

Strand Gate, Winchelsea

Strand Gate and Lookout View of Rye Bay

St Thomas the Martyr Church, Winchelsea

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