Cotswold Highlights Trail

Cotswold Highlights Trail

A fantastic walk from Chipping Campden through the quintessentially English countryside of the Cotswolds.

4 to 7 nights
45 miles
Easy to Demanding

From £430 per person

Discover the available tours

About this route

Beginning at the beautiful old town of Chipping Campden, this delightful circular walk links the show piece villages and towns that the northern Cotswolds is renowned for, including Stow-on-the-Wold, Winchcombe, Stanton and Broadway.

The Highlights trail cuts through the very heart of the Cotswolds and along the western edge of the Cotswold Hills, offering plenty of stunning scenery and varied landscapes to enjoy. Each wonderful town and village boasts its own unique history waiting to be discovered, such as the opulent Jacobean manor house in Stanway and the stunning gardens of Batsford Arboretum in Blockley, to name just a few.


© Contours Walking Holidays Cotswold Highlights Trail map
Circular trail beginning at Chipping Campden
45 miles (71 km)
19th March to 30th October

Holiday highlights

Exploring the narrow streets, ancient houses and thatched roofs of the many classic Cotswold towns and villages, including Winchcombe, Stow-on-the-Wold and Broadway.

Beginning and ending your walk in Chipping Campden and spending time uncovering its many hidden gems.

Passing through the heart of the Cotswolds Area of Outstanding Natural Beauty and admiring the stunning landscapes along the way.

Available tours

CodeTourDurationDifficultyPrice per person
COTH1 A circular trail beginning at Chipping Campden 4 nights, 3 days walking Demanding£430
COTH2 A circular trail beginning at Chipping Campden 7 nights, 6 days walking Easy£755

Cotswold Highlights Trail 4 nights, 3 days walking

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

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

Day 1

Chipping Campden to Stow-on-the-Wold. 13.5 miles (21.5km) / 1552 ft (473 m) ascent

Day 2

Stow-on-the-Wold to Winchcombe. 13 miles (21km) / 1093 ft (333 m) ascent

Day 3

Winchcombe to Chipping Campden. 18 miles (28.5km) / 2369 ft (722 m) ascent


Depart from Chipping Campden 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
£55.00 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)
£60.00 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

An extra night is the perfect way to explore the sights and sounds of the Cotswolds.

Many people choose to have an extra night in Chipping Campden. It is the loveliest, best preserved and most historically important of all the Cotswold towns. Buildings of interest include the open-sided Jacobean Market Hall, built to shelter stallholders from all weathers; the Town Hall; the 14th century Woolstaplers Hall, where the fleeces were sold and which now houses the town's museum. Opposite this is the magnificent Grevel House built in 1380. St James' Church is one of the best examples of a Cotswold 'wool' church and contains the largest memorial brass in the county, dedicated to William Grevel, 'the flower of the wool merchants of all England'.

Next to the church is the gateway and onion-topped lodges of the old manor of Campden. The manor itself was destroyed during the Civil War. Nearby, on a raised pavement, stands a superb row of Almshouses built during the reign of James I in stunning symmetry.

Stow-on-the-Wold is an attractive town with many good antiques shops and art galleries, while Winchcombe is another popular choice for a rest day. It is a charming small town with two or three inns, many attractive old Tudor houses, cottages with roses clambering over their porches and a fine church containing an altar cloth worked by Catherine of Aragon, Henry VIII's first wife. Forty-five grotesque gargoyles, each representing a local character from the 1460's adorn its outer walls. Winchcombe is also a good base for exploring Sudeley Castle.

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

Extra night (Standard)
£60.00 per person / per night

Tour Facts

Total distance: 44.5 miles (71 km)
Duration: 4 nights, 3 days walking
Minimum daily distance: 13 miles (21 km)
Maximum daily distance: 18 miles (28.5 km)
Code: COTH1 Grade: Demanding
Season: 19th March - 30th October
Start of holiday: Chipping Campden
End of holiday: Chipping Campden

Route Profile

Cotswold Highlights Trail 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 - Most convenient major city and international airports are Bristol and Birmingham.

By Rail - The nearest rail stations to the start of the trail (Chipping Campden) are either Honeybourne (about 5.5 miles away) or Moreton-in-Marsh (about 6.5 miles away).

By Bus - There is no bus service from/to Honeybourne, so a taxi would be required. There is a bus service between Moreton-in-Marsh and Chipping Campden Monday to Saturday only, but this is very infrequent at times, so a taxi may be a better option and essential on a Sunday.

From London - Trains run from London Paddington station to Honeybourne and Moreton-in-Marsh . A taxi/bus will then be required to Chipping Campden.

Return To The Start - The Cotswold Highlights walk is a circular tour beginning and ending in Chipping Campden.

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

Cotswold Round
5 to 9 nights
49 miles
Easy to Moderate
Dog friendly
From £535 per person
A walk from Moreton-in-Marsh visiting the finest towns, villages and countryside in the Cotswolds.Find Out More
Cotswold Villages Trail
7 nights
60 miles
From £750 per person
A walking holiday from Moreton-in-Marsh through the many iconic settlements of the Cotswolds.Find Out More
Cotswold Short Break
3 nights
27 miles
Dog friendly
From £325 per person
A lovely two-day walk from Bourton-on-the-Water via Winchcombe and the Windrush Valley.Find Out More

Customer reviews from the Cotswold Highlights Trail

“Very organized, easy to follow directions, great accommodations, and beautiful walks.”
Mr Litsky, USA
“I enjoyed the walking very much and was sad to have to stop. It was very well organised and the route explained.”
Ms Meldrum, Canada
“My colleagues and I have just returned from our trip to the Cotswolds. We all agree that we have had a most enjoyable time. We have had a good few days.”
Mr Cowking, UK
“All the arrangements were excellent and the walking was great. We’ve never been disappointed with any of the holidays we’ve booked with Contours. Luggage transfers couldn’t have been better.”
Mrs Wilson, UK
“Overall a wonderful walk.”
Ms Lundquist, USA
“We thoroughly enjoyed the walk and the range of accommodation. We received excellent support from Contours. Thank you. We enjoyed it all.”
Mrs Davis, UK
“Enjoyed the holiday very much. Wish I had booked for a longer walk!”
Mr Jenkins, Australia
“Had a wonderful walking holiday so thank you very much.”
Mrs Woodward, UK
“Very good holiday. Overall, very well organized and positive.”
Mr Waite, Canada
"By the Plough Inn" by Samantha Smith (2018) "By the Plough Inn" by Samantha Smith (2018)
"Hailes Abbey" by Petra Cullmann (2018) "Hailes Abbey" by Petra Cullmann (2018)
"Way down to Winchcombe" by Petra Cullmann (2018) "Way down to Winchcombe" by Petra Cullmann (2018)
"Near Hailes Abbey" by Petra Cullmann (2018) "Near Hailes Abbey" by Petra Cullmann (2018)
"Sheep at Guiting Power" by Petra Cullman (2018) "Sheep at Guiting Power" by Petra Cullman (2018)