Cobbled Mermaid Street in Rye, East Sussex, lined with historic timbered and brick houses on a sunny day.
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1066 Country Walk – Walking Holidays and Outdoor Adventures

Is it for me?
Easy going
Gentle terrain, minimal climbs, suitable for most walkers.
What will I see?
Castles, abbeys, and battlefields
High Weald ridges and woodlands
Sussex marshes and lowland valleys
Medieval towns and cobbled streets
What’s the vibe?
Cultural & story-driven
Peaceful & Relaxed
Scenic & Photogenic
Relaxed & accessible

Historic Battlefields, Rolling Countryside, and Sussex Coastlines

Follow in the footsteps of history on the 1066 Country Walk, a 31-mile (50 km) trail across East Sussex in South East England. Linking the coast at Pevensey with the medieval town of Rye, it traces the story of the Norman Conquest, weaving through the site of the Battle of Hastings and the rolling landscapes of the High Weald National Landscape.

This is a trail where walking holidays blend heritage, countryside, and seaside exploration. From castles and abbeys to marshland and ridgelines, it’s a rewarding outdoor adventure for walkers looking to combine culture and history with peaceful landscapes.

Trail Overview

Explore the Route

Pevensey to Battle
Begin at Pevensey Castle, where William the Conqueror landed in 1066. The path leads through open farmland and quiet villages, arriving at Battle Abbey, built on the site of the Battle of Hastings.

Battle to Winchelsea
From the historic town of Battle, the trail continues across the ridges and woodlands of the High Weald National Landscape, offering wide countryside views before reaching the old port town of Winchelsea.

Winchelsea to Rye
The final stage runs through lowland marshes to the medieval town of Rye, with its cobbled streets, timbered houses, and harbour atmosphere.

Stay and Explore

The route connects a string of characterful towns and villages that make ideal walking bases: Pevensey, Battle, Winchelsea, and Rye. Each offers a mix of cosy inns, B&Bs, and boutique guesthouses, plus plenty of cafés and pubs for post-walk meals.

Thanks to good rail connections (notably at Battle and Rye), the trail is accessible for weekend walking breaks as well as longer holidays. Several operators offer self-guided walking holidays with luggage transfer, making it easy to enjoy the route at a relaxed pace.

Adventure Highlights

Frequently Asked Questions

Does the 1066 Country Walk run through any National Parks or Landscapes?

Yes – much of the route crosses the High Weald National Landscape.

How long does it take to walk the trail?

Most walkers complete it in 2–3 days, though it can be split into day walks.

Is it suitable for beginners?

Yes – the route is easy to follow and mostly gentle underfoot.

When is the best time to walk it?

Spring and summer bring flowers and long days; autumn colours the Weald; winter offers quieter paths and dramatic skies.

Can I book it as a walking holiday?

Yes – several operators offer self-guided holiday packages with luggage transfer.

Walking Holidays

Coming soon!

Active Adventures

Coming soon!

Local Independent Stays

Coming soon!