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Cotswolds Way North | 7 Day Walking Tour

Tour Includes:


  • Luggage transfer between hotels 


  • B&B's or Hotels from 3*- 5*


    • Full breakfast daily at hotels except day 1

    Other Inclusions

    • Visits, tours and admissions
    • Headsets for walking tours
    • Ticket wallet & luggage tags
    • Smartphone App with GPS routs 
    • 24-hour emergency helpline 
    • Color coded routes on local maps 

    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 patch work of fields partioned by traditional honey colored 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.

    Tour Highlights 




    Day 1: Arrival

    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.


    Day 2: Chipping Campden to Stanton (10 Miles)

    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.


    Day 3: Stanton to Winchcombe (8 Miles)

    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.


    Day 4: Winchcombe to Cheltenham (10 Miles 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 Hols composer of The Planets and 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-mile descent into Cheltenham and / or the option for a taxi transfer into Cheltenham instead.


    Day 5: Cheltenham to Birdlip (12 miles)

    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.


    Day 6: Birdlip to Painswick (7 miles)

    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 featured in J.K.Rowling’s novel “A Casual Vacancy” and is also home to the Rococo Gardens which are worth a visit.


    Day 7: Return Home

    Enjoy your last morning before starting the journey home. 

       100 Spring St, Boston MA, 02132 | 1.617.327.4242