The Cotswold Circle

tarting in the regency town of Cheltenham, this tour takes you on a large circular walk through some of the nicest countryside and villages of The Northern Cotswolds before returning to Cheltenham for the last night.

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From £740.00 per person based on two people sharing in B & Bs & Village Inn all ensuite rooms.


7 nights / 8 days


6 miles to 17 miles per day


Moderate to Moderate/Challenging


March – September

The Tour

The Walking Tour

A 7 night/8 day self-guided walking holiday that offers a great Cotswold experience – the most beautiful villages, the finest views and the most interesting places. Starting in the bustling regency town of Cheltenham, you set off on your journey and enter The Cotswolds and all of its charm. Daily departures. For those who prefer not to change accommodation daily, this can adapted to a 2 base holidays with pre-arranged transfers.

This classic walk can include the beautiful town of Cheltenham on the first and last nights, to turn this into a 7 night 6 walking days holiday OR the daily distances can be reduced so that you follow the same route over 8 nights and seven walking days – please ask.

The Price

From £740.00 per person based on two people sharing in B & Bs and Village Inn accommodation with ensuite bathrooms

From £860.00 per person based on two people sharing in hotels, inns and selected B and Bs throughout the walking tour.

Single supplement depends on the level of accommodation chosen. Please ask.

What's Included
  • 7 nights B&B accommodation.

  • Luggage transfers each walking day.

  • Route notes & maps.

  • Local back-up.

The Itinerary

Day 1: Arrive Cheltenham for overnight

Day 2: Cheltenham to Winchcombe – 8 miles/13 km. Starting from the classical Pump Room, the route crosses Cleeve Hill – the highest point in the Cotswolds – to Belas Knap long barrow and descends to Sudeley Castle and the ancient Saxon capital of Winchcombe, with its fine wool church.

Day 3: Winchcombe to Broadway – 10.5 miles/17 km. Follow the pilgrims’ route to Hailes Abbey, then over the hills to Jacobean Stanway House and on to idyllic Stanton, before reaching the old coaching village of Broadway for overnight.

Day 4: Broadway to Chipping Campden – 4.5 miles/7 km. A half day’s walking over the hills via Broadway Tower with its magnificent views to Chipping Campden. In the afternoon, explore this charming town with its silversmiths and ‘wool church’, or visit Dover’s Hill, site of the annual ‘Cotswold Olympiks,’ or the beautiful gardens at Kiftsgate or the National Trust gardens at Hidcote; or spend the afternoon at nearby Stratford-on-Avon, birthplace of William Shakespeare.

Day 5: Chipping Campden to Moreton-on-Marsh – 8 miles/13 km. Through neighboring Broad Campden to charming Blockley and Batsford, famed for its arboretum and falconry centre. Then to the market town of Moreton-on-Marsh, straddling the old Roman road, the Fosse Way.

Day 6: Moreton-on-Marsh to Bourton-on-the-Water – 12 miles/19 km. After crossing the high wolds to Stow-on-the-Wold, complete with village stocks and picturesque square, the Cotswold Ring then passes through Lower Slaughter to Bourton-on-the-Water, prettily located on the River Windrush, with its many attractions.

Day 7: Bourton-on-the-Water to Cheltenham (Prestbury) – 15 miles/24 km. The Ring follows the pretty Windrush through the lovely villages of Naunton and Guiting Power. Finally, a dramatic descent from the high wolds through the meadows of the Cotswold escarpment to journey’s end in Cheltenham

Day 8: Departure after breakfast.

How Much Walking?


Distance: 55 miles (88 km). Duration: 7 nights, 8 days. 6 walking days.

This tour is of moderate difficulty. Maximum/minimum daily distances: 15 miles (24 km)/7 miles (11.2 km).

Route Summary

A 7 night/8 day self-guided walking holiday that offers the best of the Cotswold experience. Daily departures. For those who prefer not to change accommodation daily, this can adapted to a 2 base holidays with pre-arranged transfers. We will meet you to go over the route.

Tour Highlights

  • Rambling through some of the most picturesque countryside & villages in England

  • Carefully selected accommodation at which to stay

  • Transition from the bustle of Regency Cheltenham to the quiet of the hills

  • Walk past the ancient burial mound of Belas Knap on the way to Winchcombe

  • Soaking up the history of the area. Ancient abbeys, churches and houses.

  • Follow the pilgrims’ route to Hailes Abbey.

Travel Information

Arriving By Train:

Cheltenham Spa train station is served by regular trains. Trains travel from London Paddington to Cheltenham frequently, you may need to change trains once.

Arriving By Plane:

Nearest airport: Birmingham Airport (54.1km).

Other nearby airports: Bristol Airport (97.6km), London Heathrow: (164km). From London Heathrow, you can take the Heathrow Express train directly to London Paddington from where you can then take train to Cheltenham Spa

We are happy to arrange private transfers to your starting accommodation, please contact us for futher details.


There are different categories of accommodation available from B&B accommodation to Village Inns to small & luxury hotels. Ensuite rooms are booked where possible, in some B&B’s a private bathroom may be necessary.

B&B accommodation is generally in guesthouses, often private residences where some of the rooms are used for guests. They are also often smaller in size than Inns or hotels. All of our selected B&Bs will give you a warm welcome with a hearty breakfast for you in the morning. Because these are often private residences, there may not be the facilities you would expect to find in dedicated accommodation establishments. And they do not generally have options for dining in the evening.

Village Inns are generally larger, they may cater for only guests or they may also be a pub which also has guest rooms. They generally tend to have more in the way of facilities and have some kind of bar or dining options and are generally larger establishments than B&B’s

Hotels are usually the biggest of the establishments that we use and are more dedicated just to accommodation than B&B’s or Inns. There is a wide variety of hotels in The Cotswolds ranging from small hotels, to hotels with restaurants, to award winning luxury hotels.

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Cotswold Journeys offers independent walking tours, walking holidays & hiking vacations throughout The Cotswolds. With so many picturesque villages to discover, where will you walk?