Cotswold Round: Cheltenham Circuit

Cheltenham Circuit in 5 Days Walking Code: CRC6

We offer 3 itineraries walking from Cheltenham. When choosing from 4, 5 or 6 days walking consider how far you’d like to walk each day, as well as whether your choice will have you stay in your preferred locations, should you have them.

This 5 day walk is the middle ground of our 3 itineraries on the Cheltenham Circuit. Averaging 12 miles per day, you will find it more comfortable than the 4 day option. This choice includes nights in Winchcombe, Chipping Campden and Stow-in-the-Wold.

Miles Km
Day 1 Travel to Cheltenham for your first nights accommodation
Day 2 Cheltenham to Winchcombe 9 14
Day 3 Winchcombe to Chipping Campden 13 21
Day 4 Chipping Campden to Stow-on-the-Wold 15 24
Day 5 Stow-on-the-Wold to Guiting Power then transfer back to Stow-on-the-Wold 11 18
Day 6 Transfer back to Guiting Power then walk to Cheltenham 11 18
Day 7 Depart from Cheltenham after breakfast

Cheltenham to Winchcombe

This is a really pleasant start to your walking holiday. Leaving the town by the racecourse you begin a steady ascent through farmland, following hedgerows and woodland over Cleeve Common and onto Cleeve Hill, which at 330 m/1083 ft, is the highest point in the Cotswolds, and a magnificent viewpoint. Three radio masts near the summit will act as a guide. After which you enjoy a long easy decent into the village of Winchcombe following a combination of the Cotswold Way and Winchcombe Way, which at times, are one and the same.

A fascinating feature on this section of the trail is Belas Knap at the charmingly named Humblebee How. Built around 3000 BC, Belas Knap is one of Britain’s finest Neolithic long barrows. Restored on a number of occasions, the barrow is now cared for by English Heritage. Take time for a look around.

Winchcombe to Broadway

A fabulous stretch of gently undulating countryside following fields and tracks, once again making good use of the Cotswold Way and Winchcombe Way. Puck Pit Lane leads to the ruins of Hailes Abbey. Consider visiting the on-site museum where you can discover the treasures of Hailes, uncovering stories of the monks who lived and worshipped here for nearly three centuries.

Between Hailes and Broadway you are treated to the captivating crossroads hamlet of Stanway and the delightful village of Stanton. Time should be set aside to savour the sights of these two lovely locations.

Broadway to Moreton-in-Marsh

This section of the trail begins with an enjoyable but fairly steep climb up to Broadway Tower at 312 m/1024 ft. After which comes gentle level walking along the Cotswold Way into Chipping Campden. The Heart of England Way/Monarchs Way then leads you over slightly more undulating ground to Moreton-in-Marsh.

The tower on Broadway Hill is the second highest point in the Cotswolds. This iconic landmark, completed in 1798, was the brainchild of 18th century landscape designer Capabilty Brown. It was the architect James Wyatt who brought the idea to life for George William 6th Earl of Coventry. Wyatt’s Saxon tower incorporates battlements, gargoyles, turrets and even balconies.

Moreton-in-Marsh to Bourton-on-the-Water

A combination of the Monarch’s Way, Heart of England Way, Macmillan Way and Gloucestershire Way, will lead you from Moreton-in-Marsh to Bourton-on-the-Water. This is an absolutely stunning stretch of land through fields, along tracks, in and out of woodland and across beautiful meadows between picturesque villages you may never want to leave.

One such village is Stow-on-the-Wold. Stow sits, as the name suggests, on a hill, at around 245 m/800 ft. Located at the junction of six roads, its market square is a centuries old meeting place. Take time to seek out St Edward’s Parish Church whose north door is flanked by Yew Trees. It’s an impressive sight, not to be missed.

Bourton-on-the-Water to Cheltenham 

Walkers on this, the Cheltenham Circuit, as well as those on the Moreton-on-Marsh Circuit, must first aim for Guiting Power, from where their paths then split. The walk out to Guiting Power follows first, the Windrush Way then latterly the Warden’s Way/Diamond Way. A mix of meadow, track, woodland and river bank make for pleasant walking.

From Guiting Power, meadow and farm track with some time spent on quiet tarmac roads lead to Cheltenham. The walking is predominantly rural, culminating in a thoroughly enjoyable descent into Cheltenham.

Easy to Moderate

As with the Cotswold Way, this is a relatively easy trail in terms of walking. Making good use of the guidebook and maps will result in a pleasant introduction to long distance walking.

Terrain: Varied, but these are gentle wolds and not mountainous areas. The path rises and falls over the Cotswold Escarpment in the western section, and is lower, but still undulating, over farmland and through woods in the east.

What’s it like underfoot? Pretty good. Predominantly on well-maintained paths and minor roads, although there are sections across fields and open hillside which can get a bit muddy in wet weather.

How much up & down? This trail is rolling and it does go up and down a bit, with some short steeper sections, but they are not prolonged. The highest point on the trail is 330m (1083ft). Ascents and descents are usually 150 - 200m (495 - 660ft).

Signposting: No designated ‘Cotswold Round’ waymarking. There are however occasional waymarkings for other routes such as the acorn marking of the Cotswold Way.

Navigation: By following the directions in your guidebook and confirming your position on the Ordnance Survey maps supplied, navigation should be straightforward. At times, you will follow yellow arrow ‘Public Footpath’ signs. Be mindful that not all yellow arrows are relevant to your walk, so check carefully against your guidebook.

All Holidays
Accommodation Overnight Bed and Breakfast accommodation in selected hotels, farmhouses, village inns, guest houses and family B&Bs.Full English or Continental breakfast.
Guidebook A detailed guidebook with route information, maps, photos and background information.
Information of Services Along the Route A comprehensive Service Info sheet, including services such as cash points, banks, post offices, village shops, inns, cafes and taxis.
Maps Ordnance Survey Explorer (1:25000) maps covering the entire route.
Personal Itinerary A personal itinerary setting out each overnight stop, including large scale maps of each accommodation, to ensure you find it easily.
Emergency Telephone Support If you get in to difficulties during your holiday, we are always available to help, even out of office hours.
12.5% discount at Cotswold Outdoors We will issue you with a 12.5% Discount Card valid at all Cotswold Outdoor stores, and online, for the whole year on confirmation of your booking.
Luggage Transport We will transfer your luggage between each overnight stop – if you leave your luggage at the accommodation when you set off in the morning, it will be moved on to your next B&B. You only need to carry a small day sack with the clothes and provisions you require during the day’s walk.
Packed Lunches
Provided for each day’s walking and recommended on this holiday as there will not always be a handy shop or cafe on the route.
Off Road Parking If you are travelling by car we can usually arrange off road parking for the duration of your trip. (There may be a small charge for this).
Arrangement of return transport We can also arrange your transfer back to your car, (or advise you when public transport is a better option)!
What’s not Included
Evening Meals Your evening meal isn’t included in the package, but we include full details and recommendations for each evening meal in your itinerary. You will normally be within walking distance of a pub and/or restaurant, or where there is good food available at the accommodation, we’ll book that for you. Allow about £20.00 per night.
Transport to the Start & Away from the Finish Have a look at the “Travel Info” tab above for suggestions. If you’re still struggling, get in touch and we’ll help you sort it out.
Travel Insurance Even if you are based in the UK travel insurance is worth having.

Good accommodation and friendly hosts are an essential part of any holiday. We understand this and go out of our way to find the best. We put a great deal of effort into hand picking our accommodation and matching it to individual customer requirements. As well as visiting the accommodation ourselves, we ask all our customers to complete a short evaluation on each night’s accommodation, which then gives us an insight into the day-to-day operation and lets us spot any potential issues before they become a problem.

We use a variety of accommodation. Over the course of your trip you might stay in a village inn, a bed and breakfast in a converted barn, a Victorian guest house, or on a working farm. In selecting the accommodation we look for helpful, friendly hosts with good quality, characterful accommodation close to the trail. Occasionally we may use a chain hotel.

We always try to arrange en suite accommodation, i.e. rooms with their own bathrooms for each night of your stay. However, in some of the more remote locations accommodation is limited and occasionally we may have to book rooms with shared bathrooms for one or two nights of your holiday, (especially if the booking is made at short notice), but we will always let you know if this is likely to be the case.

We are happy to book single rooms on our holidays but cannot normally book more than two for any one group. Single room bookings include a supplement.

Here are some examples of the accommodation we use on the Cotswolds Round:

Lyndsay and Mark look forward to greeting guests, both old and new, at their award-winning bed and breakfast. Crossways is a classic Regency Grade II listed building, located in central Cheltenham within a few minutes’ walk of festival sites, theatres, excellent shopping, the Promenade with its fine Regency terraces, and some of Cheltenham’s excellent restaurants. Visit their website

Kate and Robin guarantee you a warm welcome at Windrush House in Broadway. A classical contemporary guest accommodation with an emphasis on old time values – courtesy, politeness, consistency and competency as well as the presence of the working owners. Windrush House is a quiet place to relax and their large landscaped garden is a haven to chill out in. Visit their website

In the picturesque village of Bourton-on-the-Water is The Old New Inn, a characterful, Grade II listed former coaching house. Built in the early 18th Century, it has recently been refurbished to a very high standard. Your hosts, Andrew and Julie, bought the hotel at the end of 2018. They have many years’ experience operating hospitality businesses. Visit their website

The Limes Guest House has been welcoming visitors since 1973. Charging £2.50 per night, it was one of the first guesthouses in Stow-on-the-Wold . Some of the guests from that time, are like old friends and return each year to see current owners Graham and Helen, who took over from Graham’s parents Valerie & Tony 19 years ago. Visit their website

General travel information for the Cotswold Round will be in your holiday pack including train and bus timetables where available.

Detailed instructions on getting to your first night’s accommodation by car, or on foot from the nearest train or bus station, will also be included in the holiday pack on individual accommodation maps.

To view train times please visit trainline where you can also purchase tickets in advance. For information on bus timetables please visit traveline

If you require secure car parking whilst walking this route, please contact us for detailed information.

Getting There:

By Air: The nearest International Airport to Cheltenham is Birmingham. Alternatives are London Heathrow or Gatwick. There is a railway station at Birmingham Airport (Birmingham International (BHI)) with frequent services to Cheltenham Spa via Birmingham New Street. From London Paddington station, regular trains run to Cheltenham Spa via Bristol Parkway.

By Public Transport: Cheltenham station (CNM) is located on the CrossCountry line direct from Bristol Parkway.

By Road: Cheltenham is located just off the M40/M5 motorways. From the M40, exit at Junction 8 following signs for A40 and continue on this road until you come to Cheltenham. From the M5, leave at Junction 11 and follow the A40 into Cheltenham.

Getting Back:

As this is a circular route you will be walking back to your starting location so you can depart by the same means you arrived.


Nestled at the foot of the Cotswold escarpment, Cheltenham is the perfect place to unwind prior to your walk, or relax and recharge at the end. Whichever you choose, Cheltenham is intimate and friendly, with a host of independent shops and incredible culinary experiences with everything from street food to Michelin starred fine dining.

Cheltenham offers a wide range of traditional and modern culture, and on account of the number, size and frequency of the Regency style buildings, Cheltenham is regarded as Britain's most complete Regency Town. There’s no shortage of parks, theatres, museums and examples of history and heritage alongside a contemporary leisure and nightlife scene.

Chipping Campden

Many people choose to spend an extra night in Chipping Campden in order to soak up the mellow atmosphere of this charming medieval market town with its beautiful honey-coloured buildings dating back to the 14th Century. It also makes an excellent base for a day trip to Stratford-upon-Avon, Shakespeare’s Birthplace, which is about an hour away by bus, (8 miles/16km) but please note that there are no buses on Sundays.

Prices GBP (£)
Accommodation, map & guidebook only £750
with Luggage Transport £792
with Packed Lunches £805
with Luggage & Lunches £844

Other Options

Extra Nights (per night) £90
Single Supplement (per night) £70
Solo Luggage Supplement (per day) £0