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Winchcombe Way

An double-loop route showcasing the northern Cotswolds with Winchcombe at its centre.

3 to 5 nights
43 miles
Moderate to Strenuous

From £270 per person

Discover the available tours

About this route

The Winchcombe Way is a fantastic trail that takes an enjoyable figure-of-eight route around the charming region of the northern Cotswolds, revealing constantly changing scenery with the town of “Walkers are Welcome” Winchcombe nestled conveniently in the middle.

The 44-mile walk offers plenty of enticing views and unique sites of interest along the way, taking in a mixture of quiet valleys, picturesque villages, tranquil woodlands and fascinating historical landmarks – such as the impressive Sudeley Castle and its pretty gardens – as well as plenty of breath-taking viewpoints, including Cleeve Common, the highest point along the trail.

© Contours Walking Holidays Winchcombe Way map
Circular trail beginning at Winchcombe
43 miles (69 km)
2nd January to 24th December

Holiday highlights

Exploring the dynamic, changing landscapes of the Cotswolds, from peaceful forests and valleys to undulating hills and the Cotswold escarpment.

Visiting the many picturesque villages along the trail and sampling a range of locally-sourced produce.

Reaching Cleeve Common - the highest point on the trail - and enjoying the wonderful, unimpeded views of the surrounding countryside.

Available tours

CodeTourDurationDifficultyPrice per person
WINCW1 A circular trail beginning at Winchcombe 3 nights, 2 days walking Strenuous£270
WINCW2 A circular trail beginning at Winchcombe 4 nights, 3 days walking Demanding£360
WINCW3 A circular trail beginning at Winchcombe 5 nights, 4 days walking Moderate£450

Winchcombe Way 3 nights, 2 days walking

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

Important information

One of the itineraries offered along the Winchcombe Way is a three-night, two-day single centre holiday, with each day taking in one of the circular loops of the trail before returning to Winchcombe at the end of each walking day.


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

Day 1

Winchcombe to Winchcombe. 21 miles (34km)

Day 2

Winchcombe to Winchcombe. 22 miles (35km)


Depart from Winchcombe 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
£42.00 per person / per night
Single Supplement
£32.00 per person / per night

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

Extra night (Standard)
£55.00 per person / per night

What's included?

  • 3 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

If you would like to extend your walking holiday to find out more about the enchanting locations along the Winchcombe Way, we can arrange for you to spend extra nights at any of the overnight stops along the route.

Dubbed the walking capital of the Cotswolds, Winchcombe is a fantastic option for an extra night or two; not only because the trail stops here several times during the holiday, but also because the town itself has ?Walkers are Welcome? status, and as such is fully stocked with all the facilities and services you may need. As well as a selection of tea rooms, coffee shops, pubs, restaurants and shops to enjoy, Winchcombe has picturesque streets lined with cottages of golden yellow stone and hidden courtyard gardens to discover, giving the impression of having stepped back in time.

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

Extra night (Standard)
£55.00 per person / per night

Tour Facts

Total distance: 43 miles (68.5 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 21 miles (34 km)
Maximum daily distance: 22 miles (35 km)
Code: WINCW1 Grade: Strenuous
Season: 2nd January - 24th December
Start of holiday: Winchcombe
End of holiday: Winchcombe

Route Profile

Winchcombe Way 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 city and international airports are Birmingham and Bristol.

By Rail - The nearest rail stations to Winchcombe are either Cheltenham Spa (about 9.5 miles away) or Ashchurch for Tewkesbury (about 11 miles away).

By Bus - Various bus services run to and from Winchcombe.

From London - Trains run from London Paddington station to Cheltenham Spa. From there a bus/taxi will be required to Winchcombe.

Return To The Start - The Winchcombe Way is a circular tour beginning and ending in Winchcombe.

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.

Routes on this trail

4 to 7 nights
43 miles
Easy to Demanding
Dog friendly
From £365 per person
A fantastic walk from Chipping Campden through the quintessentially English countryside of the Cotswolds.Find Out More
5 to 9 nights
48 miles
Easy to Moderate
Dog friendly
From £445 per person
A walk from Moreton-in-Marsh visiting the finest towns, villages and countryside in the Cotswolds.Find Out More
7 nights
60 miles
From £625 per person
A walking holiday from Moreton-in-Marsh through the many iconic settlements of the Cotswolds.Find Out More
7 to 13 nights
80 miles
Easy / Moderate+
From £625 per person
A pleasant walk from Winchcombe through the tranquil countryside of the southern Cotswolds.Find Out More
3 nights
27 miles
Dog friendly
From £270 per person
A lovely two-day walk from Bourton-on-the-Water via Winchcombe and the Windrush Valley.Find Out More
Sudeley Castle Sudeley Castle
Hailes Abbey Hailes Abbey
Cleeve Common Cleeve Common
Snowshill Manor Snowshill Manor
Cleeve Common Cleeve Common
Belas Knap Long Barrow Belas Knap Long Barrow
Cleeve Hill Cleeve Hill
Looking west Towards Alderton and Dumbleton Hills Looking west Towards Alderton and Dumbleton Hills
Stanway House Stanway House
Sudeley Castle Sudeley Castle
Hailes Abbey Hailes Abbey

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