South Downs Way Running Holiday, Trail Running South Downs Way End to End Running Retreat Winchester to Eastbourne Seven Sisters
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Over 3 nights, this point-to-point trail running adventure follows the iconic South Downs Way from end to end, tracing 170km of rolling chalk ridgelines, ancient byways and dramatic coastal cliffs from Winchester all the way to the sea at Eastbourne. Camping under the stars at carefully chosen sites along the way, we move together at a relaxed, social pace, with bags transported between camps so you only carry what you need for the day. Expect long days on the trail, hearty camp meals, classic pub dinners, and a final finish above the white cliffs of the Seven Sisters. This isn't a race - it's a shared end-to-end journey along one of Britain's most beloved long-distance trails.
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Dates & Spaces
Only 20% deposit to secure your booking.
Pay the rest any time up to 60 day before trip.
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Itinerary
Welcome to the South Downs Way, one of Britain's most iconic long-distance trails - 100 miles of rolling chalk hills, ancient drove roads, beech-shaded climbs and dramatic coastal clifftops, stretching from the historic city of Winchester all the way to the sea at Eastbourne. Join us for 4 days of trail running covering the entire route end-to-end, sleeping under canvas at carefully chosen campsites along the way. We'll run roughly 40-45km a day across four big days, taking on around 170km in total. By Day 4, the trail finally meets the coast for some of its most spectacular running, with the dramatic chalk cliffs of the Seven Sisters guiding us to the finish.
This is not a race, it's trail running as a journey. We'll move as a group at a relaxed, social pace, taking time to stop for coffee, pop into village pubs and farm shops along the way, and enjoy long evenings around camp. Your gear is transported between campsites each day, and all meals are provided - camp breakfasts, lunches on the trail, and pub dinners or campsite BBQs in the evenings. The adventure wraps up with a celebratory final dinner in Eastbourne to mark the end-to-end finish. Please note: this is a demanding multi-day trail running trip with sustained daily distances, so a solid base of trail and endurance fitness will help you get the most out of it.
Day 1
Winchester to the Edge of the Downs - 44km, 850m+
We meet early in central Winchester at 9:00 where you'll hand off your main luggage to our support driver and set off along the opening miles of the South Downs Way. The trail eases out of the city and climbs steadily into open countryside, including the long ascent of Butser Hill - the highest point on the entire route - which rewards us with wide panoramic views across the Downs. We'll take time to stop for snacks and coffee along the way, keeping the pace relaxed and sustainable. The day finishes at our campsite, where we'll settle in for the night and unwind after our first big day on the trail. Dinner is wood-fired pizza at camp, so you can take the evening to recover and relax.
Day 2
Into the Heart of the South Downs - 45km, 900m+
Day two starts with breakfast at camp before we head west, deeper into the South Downs. Covering around 45km, the route flows through classic chalk trails, long climbs, and fast open descents, with expansive views stretching across the countryside. We'll drop into the small village of Houghton for a relaxed lunch stop along the way. By late afternoon we arrive at our campsite just north of Worthing, where a comfortable pitch and a well-earned rest await. Once showered we'll head to a classic local pub for a proper dinner before turning in for the night.
Day 3
Open Ridges and Coastal Views - 42km, 950m+
Today we continue west as the landscape begins to change and the coast draws closer. The trail becomes more open and expansive, with fewer trees and long stretches of ridgeline running. On clear days, views open out toward the sea, adding a fresh sense of space and momentum to the miles. Lunch is at a local farm shop, full of delicious local goodies to refuel with. We finish the day at our campsite, where a relaxed evening awaits - complete with a well-earned BBQ and time to unwind after another full day on the South Downs Way. We're getting close to the end now.
Day 4
To the Sea & Eastbourne Finish - 40km, 1000m+
Our final day takes us all the way to the official end of the South Downs Way in Eastbourne. After breakfast at camp we set off toward the coast, where the trail delivers some of its most iconic running, with the dramatic chalk cliffs of the Seven Sisters and big sea views guiding us to the finish. Reaching Eastbourne marks the completion of four rewarding days on the trail, and we'll celebrate together with a well-earned final dinner, reflecting on the miles, the effort, and the shared experience of running the South Downs Way from start to finish.
Highlights
Challenge Level
Every Run Weekends adventure is a little different. The Overall Challenge Level is designed to give you clear, at-a-glance guidance on how demanding a trip is likely to feel as a whole. It’s not about speed or racing, it’s about the combined physical, mental, and logistical challenge across the entire experience.
All our trips are suitable for all abilities because we design the support to take good care of you. These rating are simply to help you make an informed decision as to the challenge you’ll experience. Taken together, these four elements provide a balanced, honest snapshot of what to expect, helping you choose the adventure that best matches your appetite for the challenge.
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Book with a friend
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Included
Accommodation
3 x Nights Camping - Tents provided
Running
44km, 45km, 42km, 40km
95% Trail + 3,600m Elevation
Meals
3 x Breakfast
4 x Lunch
3x Dinner
All group meals shared together
Travel
Your Bags will be transferred to each campsite every day. Run light with only what you need in the day.
Activities
4 x Trail Running days
Fire Pits and Stargazing
National Park Running
Photos
The team will be taking photos throughout the weekend. You'll be sent these via a link post weekend.
Not Included
Travel
You must make your own way to and from your Run Weekend location.
Travel Insurance. You must come prepared with appropriate travel insurance.
Extras
All drinks.
Additional food.
Snacks on run route.
Accommodation upgrades
Extra meals
Kit
Run gear as mentioned. You'll carry your run pack yourself.
Dates & Spaces
Only 20% deposit to secure your booking.
Pay the rest any time up to 60 day before trip.
Packing List
Mandatory:
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Trail running shoes with good grip.
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Running socks (2–3 pairs)
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Running T-shirt or long sleeve.
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Running shorts or leggings.
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Lightweight waterproof jacket.
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Lightweight mid-layer or thermal top
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Running vest or pack (min 6 litres)
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Soft flasks or hydration bladder (Must have carry capacity of 2 litres of water)
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Whistle (usually built into your pack)
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Head torch (emergencies)
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Small personal first-aid kit
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Personal ID / Emergency contact details
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Fully charged mobile phone and charger
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Hat or buff (for warmth or sun protection)
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Sunglasses with UV protection
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Sunscreen (SPF 30 minimum)
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Lightweight gloves
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Sleeping Bag Liner
Optional:
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Extra technical layers for variable weather
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Emergency Cash (€50-€100)
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Spare set of dry clothes for post-run recovery
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Spare shoes or sandals
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Compression socks or calf sleeves
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Lightweight towel & swimwear (for river)
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Energy gels, bars, or on-the-run snacks
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Electrolyte tablets or powder
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Small waterproof dry bag for valuables
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Running poles
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Painkillers and or Anti Inflammatories
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Waterproof phone case or backup phone
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Watch or GPS device
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Lightweight running cap or visor
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Waterproof phone pouch or small zip bag
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Casual clothing for evenings
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Power bank & charging cables
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Travel adaptor
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Ear plugs & eye mask
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Toiletries & travel-sized essentials
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Small notebook or journal
Getting to us
Meeting Point
Your Run Weekend will commence in central Winchester at 9am on Day 1 (exact location shared in your welcome pack). Please plan to arrive in Winchester the evening before, or very early on Day 1, to allow for a relaxed start. Once your travel is booked, email your arrival details to contact@runweekends.com.
Arrival & Departure Times
Please plan to arrive in central Winchester by 9am on Day 1, in time for the start of our first day's running.
The Run Weekend will conclude in Eastbourne in the early evening of Day 4, after our finish at the official end of the South Downs Way and a celebratory group dinner. Your main luggage is transported between campsites each day by our support vehicle, so you only carry a day pack on the trail.
Getting to Winchester, UK
Winchester is easily reached by train from London Waterloo in approximately one hour. From Eastbourne at the end of the trip, regular trains run back to London Victoria in around 90 minutes. Travel to and from the meeting and finish points is not included and is the responsibility of each guest. Full meeting details and local travel tips will be provided in your welcome pack.
Important Info: Trip Confirmation
This trip operates with a maximum number of 16 guests and will be confirmed once a minimum number of 10 guests have booked. We will inform you once this number has been reached. If you wish to book travel in advance, please ensure your travel booking is fully refundable. We do not hold liability for loss of flights if this trip doesn't run. If the trip doesn't run your deposit along with any balance paid will be fully refunded.
All our trips are shared rooms with the same genders
Together Is Better
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