The Cotswold Way is one of the UKs managed National Trail footpaths, running 103 miles from the market town of Chipping Campden in the north of The Cotswolds, to the spa town of Bath in the South. The route crosses typical Cotswold countryside with a patchwork of fields partioned by traditional honey coloured dry stone walls across rolling hillside. The route stops at a plethora of traditional villages and small towns. This tour focuses on the northern part of the trail from Chipping Campden to Painswick, typified by the traditional Cotswold ‘chocolate box’ villages that the area is famous for.

6 Nights 7 Days Available Chipping Campden, England

By Rail: The nearest railway station to the start at Chipping Campden is at Moreton-in-Marsh, which is easily reached from London by train. Moreton-in-Marsh is approximately 8 miles from Chipping Campden and we suggest a short taxi ride from the station which we are happy to arrange on guests’ behalf.

By Car: The market town of Chipping Campden is relatively small so we instead recommend arrival to Cheltenham where we are able to provide parking and a transfer to Chipping Campden. Cheltenham is easily accessible via the M4/M5 route or by the A40 from London via Oxford. 


Hotel Category

B&Bs, Hotels and Inns (3*) or Luxury Hotels (5*). Please note the Luxury version includes some taxi transfers at the beginning or end of some days.

Luggage Transfer

The tour includes transfer of luggage as stated. The tour information pack provided to the clients contains luggage tags from Compass Holidays. The clients name and the hotels used throughout the stay will be on these tags. They should be fixed to the luggage. In the morning the luggage should be left at the reception for collection. Luggage is collected after 9.30am and delivered to the next hotel before 4.30pm.

Grade (Difficulty)

This grade of this tour is moderate.

Start Location

  • Chipping Campden

End Location

  • Painswick

Daily Distance Range

  • Minimum:7 miles / 11 km per day
  • Maximum:12 miles / 19 km per day

Duration (Nights)

This tour runs for 7 days, 6 nights and 5 days walking, but can be extended or decreased by changing the daily distance.


This tour is available from January until December.

What we'll give. What we won't

What is included in the tour

  • Accommodation at the stated category with breakfast
  • Luggage Transfers
  • Full Tour Pack
  • Smartphone App with GPS routes
  • 24-hr emergency helpline

What is NOT included in the tour

  • Lunch, Dinner & Drinks
  • Entrance to attractions
  • Buses and/or Ferries unless otherwise stated
  • Tourist Taxes where applicable

Arrive Chipping Campden and stay overnight. Chipping Campden is a traditional market town, with preserved historic features dating back as far as the 14th century. It is also one of the earliest examples of deliberate town planning with a charter from King Henry II to set out a plan of the town.

A: Chipping Campden to Stanton (10 miles / 16 km)

After leaving the town, the trail takes you out onto the Cotswold escarpment with stunning views from Dover’s Hill. This is where the annual ‘Olimpick’ games were held in 1612, with leapfrog, wrestling and shin-kicking events happening each year. The walk continues across the fields to Broadway Tower and then through the village of Broadway with its historic connections with the Arts & Crafts movement. Stanton is built entirely of Cotswold stone and will be your rest stop for the night.

Stay overnight in Stanton. Luggage will be transferred. Please note Stanton is a small village, so if no accommodation is available, the walk will be extended slightly to the next village of Stanway or Wood Stanway.

B: Stanton to Winchcombe (8 miles / 12.5 km)

After a steep climb up onto the escarpment, you will be rewarded with magnificent views across the Vale of Evesham towards the Malverns. Passing the Iron Age hill fort of Beckbury Camp, the Trail continues through farmland into the Cotswold town of Winchcombe. Stay overnight in this “Walkers are Welcome” certified town and explore its Neolithic, Roman and Medieval past. A highlight of the village is Sudeley Castle & Gardens, the only private castle in the UK, and final resting place of Catherine Parr, Henry VIII’s final wife.

Stay overnight in Winchcombe. Luggage will be transferred.

C: Winchcombe to Cheltenham (10 miles / 16 km + 2-3 miles into Cheltenham)

Leave through the Sudeley Estate, climbing steadily to the ancient Neolithic long barrow of Belas Knap to Cleeve Hill –the highest point in The Cotswolds. The route continues across Cleeve Common with extensive views over Cheltenham to Gloucester and the distant Malvern Hills, before you continue onto Charlton Kings Common with its breath-taking views across Cheltenham and the Severn Vale. Follow the escarpment onto Leckhampton Hill –look out for the distinctive rock pillar known as the Devil’s Chimney -before turning off The Cotswold Way and descending into Cheltenham via The Gustav Holst Way. Cheltenham is the most complete Regency Town in the UK with extensive period architecture, a fantastic foodie scene and museums attributed to Cheltenham’s famous sons –Gustav Holst composer of The Planetsand Edward Wilson, naturalist and fellow casualty on the Scott Antarctic expedition.Please note although only 10 miles along The Cotswold Way, there is an extra two-miledescent into Cheltenham and / or the option for a taxi transfer into Cheltenham instead.

Stay overnight in Cheltenham. Luggage will be transferred.

D: Cheltenham to Birdlip (12 miles / 19 km)

The trail follows quiet tracks, lanes and paths into Crickley Hill Country Park, with its excellent viewpoints and information about the archaeological history, as well as a great café for a pitstop. There is evidence of historic settlements from as early as the Neolithic Period, as well as an Iron Age Hill Fort, indicating many periods of occupation. The trail then crosses the undulating grassland of Barrow Wake before heading into woodland to emerge at Birdlip.

Stay overnight in Birdlip. Luggage will be transferred.

E: Birdlip to Painswick (7 miles / 11 km)

From Birdlip, the trail passes the remains of Great Witcombe Roman Villa, through magnificent beech woodlands and on to Coopers Hill, the site of the crazy annual cheese-rolling event every May which sees competitors chase a cheese wheel down the very steep slope. The route then emerges onto the common land of Painswick Beacon, where the ramparts of an Iron Age hill fort can clearly be seen. The section ends in the picturesque town of Painswick, the mid-point of the Cotswold Way. Painswick recently featuredin J.K.Rowling’s novel “A Casual Vacancy” and is also home to the Rococo Gardens which are worth a visit.

Stay overnight in Painswick or depart. Luggage will be transferred.

The nearest train station is Stroud or guests can return to Cheltenham via transfer and depart from Cheltenham train station as an alternative.


The routing is subject to accommodation availability and will run from A-E as above. Extra nights can be added in Chipping Campden, Cheltenham and Painswick if desired. 

Important Information


The correct clothes are important to ensure comfort during each walk. We suggest avoid anything with seams and buttons in sensitive areas. Clothing should take moisture from the body to the outside. Sweatshirts, thin pullovers and breathable jackets are ideal companions during the cooler days. Take light, waterproof jackets and trousers in case there is rain. On hot days we suggest a cap or hat and sunglasses to protect from the sun.

What makes this tour special
  • Discover the villages of Chipping Campden, Winchcombe and Painswick
  • Beautiful walks along rolling countryside
  • All taxes and surcharges included
  • Perfect tour for solo travellers, couples and families
Pickup point
Chipping Campden, UK View on Map