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United Kingdom
England
South East England
East Sussex
Rother
Icklesham

1066 Country Walk and Winchelsea Loop

Moderate

6

runners

1066 Country Walk and Winchelsea Loop

00:53

7.37km

80m

Running

Jog this moderate 4.6-mile loop through Winchelsea and the High Weald, featuring historic sites and scenic views of Rye Bay.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

High Weald AONB

Waypoints

A

Start point

Bus stop

Get Directions

1

23 m

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 …

Tip by

2

318 m

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 …

Tip by

3

4.43 km

The Watcher is one of the evocative sculptures along the long-distance 1066 Country Walk route. This sentry is beautifully carved from wood and watches for the invading army. He stands by Wickham Manor Farm.

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4

6.20 km

Remains of St. Leonard's Windmill

Highlight • Viewpoint

This viewpoint is located right where the St. Leonard's Windmill used to stand. In fact, you can see some of its ruins. This windmill was built in the early 18th century but was destroyed in the October hurricane of 1987.

Tip by

5

7.00 km

Pipewell Gate (Ferry Gate)

Highlight • Monument

Pipewell Gate gave access to the ferry and later to the road which led from Winchelsea to Rye.

Its alternative name is Ferry Gate. It is newer than the others. …

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B

7.37 km

End point

Bus stop

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Way Types & Surfaces

Way Types

5.14 km

1.24 km

570 m

236 m

164 m

Surfaces

3.06 km

2.09 km

1.69 km

349 m

175 m

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Elevation

Elevation

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

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Weather

Powered by Foreca

Friday 29 May

23°C

13°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to jog the Winchelsea Loop?

This specific loop is designed for jogging and typically takes around 50-55 minutes to complete. The total distance is approximately 7.4 kilometers (4.6 miles).

What is the starting point for the Winchelsea Loop and where can I park?

The loop starts and ends in Winchelsea. While specific parking details for this exact loop aren't provided, Winchelsea generally offers parking options within the town. For public transport, Winchelsea has a train station, making it accessible by rail.

Is the Winchelsea Loop suitable for beginner joggers?

The Winchelsea Loop is rated as 'moderate' difficulty for jogging. While some sections of the broader 1066 Country Walk can be quite challenging, this specific loop offers a varied experience. Flatter sections along the Royal Military Canal are suitable, but you should be prepared for some rolling hills and potentially uneven surfaces, so sturdy footwear is recommended.

What kind of terrain can I expect on this route?

The terrain on this loop is mixed. You'll encounter grassy hillsides, ancient woodlands, and some paved sections within Winchelsea. Expect varied surfaces, including potentially uneven paths, especially in the more rural parts. The route passes through the High Weald Area of Outstanding Natural Beauty, offering diverse landscapes.

What historical or natural sights will I see along the way?

The route is rich in history and natural beauty. You'll pass by significant landmarks such as St Thomas the Martyr Church, Winchelsea, Strand Gate and Lookout View of Rye Bay, and The Watcher Sculpture on the 1066 Country Walk. Other notable features include the Remains of St. Leonard's Windmill and Pipewell Gate (Ferry Gate). You'll also enjoy views of atmospheric marshes, water meadows, and flat farmland.

Does this route connect with other trails?

Yes, this loop incorporates sections of several well-known paths. Approximately 55% of the route follows the 1066 Country Walk, 44% is part of the Saxon Shore Way, and about 19% overlaps with the National Cycle Route 2 Dover to Hastings. A small portion (8%) also uses the Spring Steps.

Is the 1066 Country Walk and Winchelsea Loop dog-friendly?

Yes, the 1066 Country Walk and its loops, including this one, are generally dog-friendly. However, as the route passes through farmland and areas with wildlife, it's essential to keep dogs under control, preferably on a leash, especially near livestock or sensitive habitats.

Are there any permits or entrance fees required for this area?

No, there are no specific permits or entrance fees required to access the 1066 Country Walk or the Winchelsea Loop. The trail passes through public rights of way within the High Weald Area of Outstanding Natural Beauty, which is freely accessible.

What are the best times of year to jog this route?

The route can be enjoyed year-round, but spring and autumn offer particularly pleasant conditions with milder temperatures and beautiful scenery. In spring, you'll see wildflowers, while autumn brings vibrant foliage. Summer can be warm, and winter might involve muddy sections, so dress appropriately for the weather.

Are there places to eat or drink near the trail?

Winchelsea, the starting and ending point of the loop, is a historic town that offers options for refreshments. You can find local pubs and potentially cafes within the town to refuel after your jog.

What should I wear or bring for jogging this route?

Given the varied terrain, sturdy, comfortable jogging shoes with good grip are highly recommended. Dress in layers suitable for the weather, as conditions can change. Bringing water is advisable, especially on warmer days. A small backpack for essentials like snacks, a phone, and a light jacket is also a good idea.

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