Circular Walks in the Cotswolds

Circular Walks in the Cotswolds

A selection of circular walks through the beautiful countryside of the Cotswolds.

3 to 9 nights
27-60 miles
Easy to Demanding / Strenuous

From £365 per person

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About the trail

Strewn with countless pretty villages built by medieval merchants, the Cotswolds fulfils most people's idea of an idyllic English landscape. While walking in the Cotswolds, you will find neat fields, rolling green hills, ancient woodland and clear streams, combined with simple stone cottages and historical landmarks to create a truly unique picture of timeless beauty. Our selection of circular trails explores the scenery, settlements and stories that make the Cotswolds such a wonderfully special place to discover on foot.

Looking for the full Cotswold Way National Trail? Click here.

Choose your route

  • Cotswold Villages Trail
  • This route includes dog friendly tour options Cotswold Round
  • This route includes dog friendly tour options Cotswold Highlights Trail
  • This route includes dog friendly tour options Cotswold Short Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

About this route

4 to 7 nights
45 miles
Easy to Demanding
2nd January to 24th December
Includes Dog-Friendly Tours

From £525 per person

Cotswold Highlights Trail

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.


Available tours

Code Tour Duration Difficulty Price per person
COTH1 A circular trail beginning at Chipping Campden 4 nights, 3 days walking Demanding £525
COTH2 A circular trail beginning at Chipping Campden 5 nights, 4 days walking Moderate / Demanding £650
COTH3 A circular trail beginning at Chipping Campden 7 nights, 6 days walking Easy £900

Short breaks

Code Tour Duration Difficulty Price per person
COTSB A circular trail beginning at Bourton-on-the-Water 3 nights, 2 days walking Moderate £365

Cotswold Highlights Trail 4 nights, 3 days walking

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

Important information

This tour is available to book all year, however out of season from November to March, there may be a small supplement for luggage moves, which will be moved by taxi rather than the usual luggage courier.


Travel to Chipping Campden where your first night's accommodation will be 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 in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

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
£65.00 per person / per night
Single Supplement
£55.00 per person / per night

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

Extra night (Standard)
£65.00 per person / per night
© Contours Walking Holidays Cotswold Highlights Trail map
Circular trail beginning at Chipping Campden
45 miles (71 km)
2nd January to 24th December

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.

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)
£65.00 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: 2nd January - 24th December
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 to Chipping Campden, 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 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.
"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)

Customer reviews from the Cotswold Highlights Trail

“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
“Had a wonderful walking holiday so thank you very much.”
Mrs Woodward, UK
“The first two days were pretty good and the luggage transfer was well executed.”
Mr Buhaly, 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
“We had stunning weather and great accommodations.”
Mr Rowe, USA
“Overall a wonderful walk.”
Ms Lundquist, USA
“We had a wonderful time and perfect cloudy weather.”
Ms Monahan, USA
“Great directions, very responsive to concerns and questions. Everything went according to plan. Accommodations were excellent, scenery and landscapes were as advertised. Contours was recommended by a friend and I will be sure to recommend you to my friends as well.”
Mr Pavlidis, 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
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