South Downs Way Trail Running

South Downs Way Trail Running

A self-guided trail running holiday from Winchester to Eastbourne.

4 to 7 nights
102 miles
Easy / Moderate to Strenuous

From £595 per person

Discover the available tours

About this route

Quality running can be found on the 100-mile (160 km) South Downs Way National Trail, where the terrain underfoot is excellent throughout.

The trail offers historic sites, expansive views and, at the finale, spectacular coastal scenery. A few steep hills are thrown in, to test the fitter runner.

Opt for the coastal alternative and you'll have to battle your way up the rolling hills of the Seven Sisters, the downfall of many a runner in the Beachy Head Marathon.

The gorgeous, postcard-perfect view is your reward for your labours. An irresistibly inspiring place at sunset.

© Contours Walking Holidays South Downs Way Trail Running map
102 miles (163 km)
1st April to 30th September

Holiday highlights

Enjoying open tracts of countryside as you rove along the Downs ridges, all within two hours of London.

Summitting the downland viewpoints of Beacon, Butser and Bignor Hills, Ditchling Beacon and Firle Beacon.

Arriving in Eastbourne to breath-taking views from Birling Gap, Seven Sisters Cliffs, and Beachy Head.

Available tours

CodeTourDurationDifficultyPrice per person
R-SDW2 From Winchester to Eastbourne 4 nights, 3 days running Strenuous£595
R-SDW3 From Winchester to Eastbourne 5 nights, 4 days running Demanding£685
R-SDW4 From Winchester to Eastbourne 6 nights, 5 days running Moderate£770
R-SDW5 From Winchester to Eastbourne 7 nights, 6 days running Easy / Moderate£845

South Downs Way Trail Run 4 nights, 3 days running

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather

Travel to Winchester where your first night's accommodation has been booked

Day 1

Winchester to Cocking. 35.5 miles (56.5km) / 4104 ft (1251 m) ascent

Day 2

Cocking to Pyecombe. 32.5 miles (52km) / 4016 ft (1224 m) ascent

Day 3

Pyecombe to Eastbourne. 34 miles (54km) / 4108 ft (1252 m) ascent


Depart from Eastbourne after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation; should your accommodation be further than this, transfers will be provided as standard.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£60.00 per person / per night
Single Supplement
£45.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

What's included?

  • 4 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

Choosing to add an extra night or two into your trail running holiday allows you more time to explore the various destinations that the magnificent South Downs Way visits on its race to the coastline; whatever your tastes, there is a location guaranteed to satisfy your needs.

An extra night's stay in Winchester could make an excellent start to your holiday. A walk up St Giles Hill offers spectacular views over the city, while a visit to Winchester Cathedral, one of Europe?s largest cathedrals, offers an insight to a whole range of treasures, including Jane Austen?s tomb and the Winchester Bible. For fans of Arthurian legend, the Great Hall of Winchester Castle features the round table, while a stroll through the city reveals Georgian buildings, Saxon streets and the gothic architecture of the Victorian Guildhall.

If you would like to spend some more time exploring at the end of your holiday, consider Eastbourne for an extra night. With spectacular views from Beachy Head and a host of historic locations such as Redoubt Fortress, as well as shops, parks, gardens, restaurants, museums and galleries, there is plenty to serve as reward after completing your run. The Sussex Spa at the Grand Hotel also offers a range of wellness facilities to help with your recovery, including swimming pools, a gym, a whirlpool spa, a sauna and steam room and a choice of spa treatments and massages to ease tired muscles.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

Tour Facts

Total distance: 101.5 miles (162.5 km)
Duration: 4 nights, 3 days running
Minimum daily distance: 32.5 miles (52 km)
Maximum daily distance: 35.5 miles (56.5 km)
Code: R-SDW2 Grade: Strenuous
Season: 1st April - 30th September
Start of holiday: Winchester
End of holiday: Eastbourne

Route Profile

South Downs Way Trail Run Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major cities and international airports are Southampton, Bournemouth, London Gatwick and London Heathrow.

By Rail - There is a rail station at the start of the trail (Winchester) and also at the end of the trail (Eastbourne).

By Bus - Various bus services run to Winchester and from Eastbourne.

From London - Trains run from London Waterloo station (and occasionally also Paddington on a Sunday) to Winchester.

Return To The Start - The easiest way to return to the start of the trail, is to take the train from Eastbourne to Winchester.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.