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 £250 per person

More holidays on the Circular Walks in the Cotswolds trail

Winchcombe Way

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.

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.

Select Your Tour

WINCW1 Winchcombe Way (3 nights, 2 days walking)
Looking for a different itinerary? Choose from 3 tours on this route.
£250 per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather

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.

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 walk 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 walking on your own, or are part of a group but require a room of your own, then the Solo Walker or Single Supplements apply respectively:

Solo Walker Supplement
£35.00 per person / per night
Single Supplement
£25.00 per person / per night

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

Extra night (Standard)
£58.00 per person / per night

What's included?

  • 3 nights accommodation in en-suite rooms with private bathrooms (where available) in selected hotels, inns and guesthouses along the trail.
  • 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)
£58.00 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

Detailed instructions on how to get to the start of the holiday and back from the end, are sent to you on booking. 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.

It is very easy to travel to the start (and return home from the end) of the holiday using public transport. Please click here for more information.

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.
Sudeley Castle
Hailes Abbey
Cleeve Common
Snowshill Manor
Cleeve Common
Belas Knap Long Barrow
Cleeve Hill
Looking west Towards Alderton and Dumbleton Hills
Stanway House
Sudeley Castle
Hailes Abbey