Early Bird Sale2027 Walks & HikesSave Now
2
introductory to moderate
Activities
  • self guided walk
Accommodation
  • 5 nights Hotels and B&Bs
Meals
  • 6 Breakfasts

6 Days£910GBP

View Inclusions

Overview

Trip Code: W66

Trip highlights

  • Follow William the Conqueror’s 1066 journey from Pevensey on foot
  • Cross the wildlife-rich wetlands of the Pevensey Levels
  • Discover where William conquered England at the Battle of Hastings
  • Step back in time at Pevensey and Herstmonceaux Castles
  • Quaff a pint of real ale in ancient villages Icklesham, Winchelsea and Rye
  • Discover medieval Winchelsea, its gateways, church and historic cellars

On 28 September 1066, William, Duke of Normandy, and his army landed at Pevensey. Sixteen days later, just 17 miles away, William defeated the Anglo-Saxon King Harold at the Battle of Hastings, changing the course of English history.

The 31-mile 1066 Country Walk follows this remarkable chapter in England’s past, beginning at Pevensey Castle and crossing the countryside associated with the Norman Conquest. Walk across the atmospheric Pevensey Levels and through rolling farmland, ancient woodland and historic villages to Battle Abbey, built on the traditional site of the Battle of Hastings. From Battle, continue through the High Weald National Landscape, passing old churches, farms, country estates, oast houses and windmills, with welcoming village pubs and cafés along the way. The journey leads through Icklesham and medieval Winchelsea before finishing among the historic streets of Rye.

Relatively easy and low-level, this is a walk where landscape and history come together – following the story of 1066 while discovering some of the most attractive countryside, villages and historic towns of East Sussex.

Countries:

England

Starting Point:

Pevensey

Finishing Point:

Rye

Itinerary

Expand all | Collapse all

Make your way to Pevensey, the bay where William, Duke of Normandy, landed with his invasion fleet of 700 ships on September 28th, 1066. William used the 4th century Roman fort of Anderida (now Pevensey Castle) as a secure stronghold before making the march to Hastings. The castle is managed by English Heritage and is worth a visti at the start of your journey on the 1066 trail. Pevensey is easily reached from London Victoria train station, with the rail journey taking around 1 hr 40 mins. Accommodation: Overnight in a hotel or inn close to the sea front in Pevensey. (Note that accommodation here is limited, if so, you may stay in Eastbourne which is just one additional stop on the train).

Meals:  B

Begin your walk on the 1066 trail at Pevensey Castle. The castle itself has a long history, with its imposing walls incorporating the remains of a Roman fort dating from the 3rd century. The route heads north across the Pevensey Levels, an extensive area of low-lying wetland characterised by open grazing marshes, drainage channels and broad skies. This is predominantly flat walking, following footpaths across fields and crossing a series of small bridges over the waterways that criss-cross the Levels. After several miles across the marshes, the route climbs gently onto higher and firmer ground around Church Farm. The landscape gradually changes, with the open wetlands giving way to the hedgerows, farmland and pockets of woodland of the Sussex countryside. Continue towards Herstmonceux Castle, a striking 15th-century red-brick moated castle set within extensive grounds. Nearby are the distinctive domes of the Observatory Science Centre, formerly part of the Royal Greenwich Observatory. Accommodation: Overnight in a comfortable B&B once the home of the local blacksmith.

Meals:  B

Leaving Herstmonceux, the route continues through stretches of woodland and the rolling Sussex countryside towards Battle. Along the way, pass Tent Hill, traditionally associated with one of the armies that gathered in the area before the Battle of Hastings. Arriving in Battle brings you to one of the most significant historic sites in England. Battle Abbey stands on the traditional site of the Battle of Hastings, where William the Conqueror defeated King Harold Godwinson on 14 October 1066. Following his victory, William ordered an abbey to be built on the battlefield as an act of penance for the bloodshed. According to tradition, its high altar was positioned on the spot where King Harold fell. Although much of the medieval abbey is now in ruins, substantial remains survive, including the impressive gatehouse and parts of the church, cloister and monastic buildings. Accommodation: Overnight in a traditional inn in Battle.

Meals:  B

Walk through ancient woodland and farmland before reaching the village of Westfield. Continue to Icklesham, home to the Grade I-listed All Saints Church, which retains a number of Norman features. The village also has another traditional country pub, the Queen’s Head, as well as Hogg Hill Windmill, which has been used as a recording studio by Paul McCartney. On the approach to Winchelsea, pass 17th-century Wickham Manor, once owned by William Penn, founder of Pennsylvania, before entering the historic town through one of its medieval gates. Winchelsea has a fascinating history. The present town was established by King Edward I after the original settlement, once an important medieval port, was lost to the sea in the 13th century. At its heart is St Thomas the Martyr Church, where comedian and writer Spike Milligan is buried. His gravestone famously carries the epitaph “I told you I was ill” although, following restrictions on the wording, it was inscribed in Irish Gaelic, making it easy to miss. You may wish to visit Winchelsea Court Hall Museum or discover another side of the town’s history underground. At least 50 medieval cellars survive beneath Winchelsea, originally used by merchants to store wine and other goods. Guided cellar tours can be booked locally. Accommodation: A friendly B&B in the town.

Meals:  B

As today’s walk is short, spend some time exploring Winchelsea before setting out on the final section of the 1066 Country Walk. You could also visit Charles Palmer Vineyards for an 11am vineyard tour (Wednesday–Saturday, advance booking required) or sample Sussex wines at the Cellar Door Lounge. Continue via Cadborough Cliff to Rye, bringing your journey through 1066 Country to an end. While much of Rye’s visible history post-dates the Norman Conquest, its medieval streets and former importance as a coastal port provide a fitting finale to a walk that began at William the Conqueror’s landing place at Pevensey. Take time to explore St Mary’s Church, the Gun Garden and Rye’s historic streets before celebrating the end of the walk with a locally brewed ale at the Mermaid Inn, one of the town’s best-known historic buildings. Accommodation: Overnight at a characterful local inn in Rye.

Meals:  B

Depart after breakfast. Rye has its own railway station, with connections to London taking just over an hour, making onward travel straightforward. Alternatively, extend your stay in East Sussex and spend some time exploring the distinctive landscapes and historic villages of Romney Marsh.

Meals:  B

Map

Elevation

The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.

Inclusions

What's included

  • 5 nights Bed and Breakfast
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 20kg
  • Digital information pack including navigation app, route notes & maps
  • Emergency hotline

  • Entry fees into castles, Battle Abbey and stately homes
  • Transport
  • Lunch and Evening meals
  • A supplement will apply if you are travelling solo or book a single room
  • Excess luggage
  • Guide - this is a self guided holiday
  • Travel insurance

Accommodation

Inns, B&Bs and Small Hotels

You will stay in a range of Sussex hotels, inns and guesthouses, all chosen for their local character, proximity to the walking route and comfort. Rooms will have private bathrooms and generally a TV and tea and coffee making facilities. An English breakfast will usually be served and some of the accommodations have bars and restaurants specialising in locally-sourced food. Note that for the dates of your tour we may not be able to get you into the accommodation described. We will endeavour to get you into a similar standard of accommodation nearby, but please appreciate that there are limited accommodation options in rural England. Also, although we aim to get you into accommodations with ensuite rooms, this is not always possible.

Trail Surface

Grassy paths, woodland trails & lanes

The 1066 Country Walk follows a mixture of grassy field paths, farm tracks, woodland trails and quiet country lanes, with some short sections on surfaced roads and village streets. Across the Pevensey Levels, paths cross low-lying grazing marshes where the ground can be wet, muddy and occasionally waterlogged after heavy rain. Further along the route, expect undulating paths through farmland and ancient woodland, with uneven, muddy and potentially slippery sections in wet conditions. Sturdy, waterproof walking footwear is recommended.

Suitability

introductory to moderate

2

We grade this walk as Introductory to Moderate. The walking is straightforward and generally low-level, following a mixture of farm tracks, field paths, woodland trails and quiet country lanes across gently undulating countryside. Some sections can be muddy, wet or uneven, particularly after rain. Walks vary up to approximately 18 km / 11 miles, with around 2–5 hours of walking each day. A reasonable level of fitness and some experience of walking longer distances will help you get the most from the trip.

Departure dates

Daily from 12 Mar - 29 Oct

Priceper person from

£910GBP

Options & Supplements*
    *Prices listed are per person

Frequently Asked Questions

Expand all | Collapse all

The walk follows a landscape closely associated with the Norman invasion of England in 1066. It begins at Pevensey, where William the Conqueror landed in September 1066, and passes through Battle, the site traditionally associated with his victory over King Harold Godwinson on 14 October 1066.

The major historic sites include Pevensey Castle and Battle Abbey, together with medieval churches, villages and towns along the route. The walk finishes in Rye, whose historic streets and buildings reveal how this strategically important stretch of the Sussex coast developed in the centuries after the Norman Conquest.

The route combines low-lying wetlands, farmland, woodland, country lanes and rural footpaths. The opening section across the Pevensey Levels is predominantly flat, although conditions can be wet and muddy after rain. The countryside becomes more undulating as the route progresses inland.

Yes. Battle Abbey stands on the traditional site of the Battle of Hastings. You can explore the battlefield and abbey grounds, where an audio guide explains the events of 14 October 1066 and the story of William the Conqueror’s victory over King Harold.

Rye provides a fitting conclusion to a journey through 1066 Country. While much of its surviving architecture post-dates the Norman Conquest, its medieval streets, defensive structures and history as an important coastal port continue the story of this strategically significant part of southern England.

There are opportunities to visit traditional pubs in villages including Westfield and Icklesham, while Winchelsea and Rye offer further choices. Near Winchelsea, Charles Palmer Vineyards also offers vineyard tours on selected days and the opportunity to sample Sussex wines.

Rye has its own railway station, making onward travel to London straightforward. Alternatively, you can extend your stay and explore more of the surrounding coast and countryside, including Romney Marsh.

Trip reviews

Why travel with us

Personal Experience

We've been exploring the world on foot for over five decades, and our passion for walking runs deep. Having hiked nearly every corner of Europe, we take pride in sharing the joy, freedom and perspective that only travelling on foot can bring, all with the exceptional service and care our travellers know us for.

Great Value & Quality

Our trips offer excellent value for money, with everything you need for a seamless walking holiday. Each package includes detailed route notes, maps and navigation app, luggage transfers, and comfortable locally run accommodation. We take care of the planning, so you can simply enjoy the walk.

Self-Guided Specialists

We've been operating self-guided active holidays since 1973, taking care of every detail so you can relax and explore at your own pace. With many walking and hiking tours departing daily, you'll enjoy the freedom and flexibility to travel when it suits you.