Our specially-designed northern Cotswolds walking itinerary begins in Stratford-upon-Avon, recognisable for its distinctive timber-framed Tudor houses and as the birthplace of William Shakespeare. We follow the famous Monarch’s Way — the escape route used by King Charles II after his defeat by Cromwell — to join the Cotswold Way at Chipping Campden. This stunning region is home to chocolate-box villages surrounded by picture-perfect countryside.
This is quintessential England as described in Jane Austen’s Persuasion and Laurie Lee’s Cider with Rosie. Discover the delightful honey-coloured villages of Stanton and Painswick for which the Cotswolds is famous.
Meander through a patchwork of sheep-dotted fields, see miles of enchanting dry stone walls and enjoy quiet country lanes.
Get Ready For
- Historic Painswick often referred to as “The Queen of the Cotswolds”
- Stunning views of beautiful country-side atop the Cotswold escarpment
- ‘Take tea’ in the many quintessential Miss Marple reminiscent tea-rooms
- Wander through the small medieval market town of Chipping Campden
- Enjoy fields of frolicking Cotswold sheep known as the ‘Cotswold Lion’
- Visit folly castle Broadway Tower for your Instagrammable photo opportunity
Make your way to the flower-filled medieval market town of Stratford-upon-Avon. Explore its Shakespeare theme with a visit to Sharespeare’s Birthplace and his wife Anne Hathaway’s Cottage. Depending on timing, you may be able to take in a play at the Royal Shakespeare Theatre. You can also visit the Holy Trinity Church, Shakespeare’s final resting place.
STRATFORD-UPON-AVON TO CHIPPING CAMPDEN (24KM)
Today you begin your Cotswold adventure beginning with a short walk along the River Avon and following the Monarch’s Way to Chipping Campden. At the end, you will find a tiny historic market town with stunning examples of Cotswold stone craftsmanship and a history steeped in wool trading. Chipping Campden is extraordinarily beautiful and one of the loveliest Cotswolds villages, so try to make time to savour the numerous tea shops, attractive high street stores and storybook cottages.
Total ascent: 194m / descent 93m
CHIPPING CAMPDEN TO STANTON (16KM)
Today you will walk up and along the Cotswold escarpment. Take in the lovely views over splendid countryside from Dovers Hill. The walk takes you past Broadway Tower, a folly built in 1799. Here you’re at the second highest point of the walk (312m). Enjoy a break at the cafe, before continuing to Stanton through stunning countryside with rolling sheep-filled farmland and pretty barns. Idyllic honey-coloured Stanton remains almost unchanged for over 300 years and has been described as the ‘most ridiculously beautiful’ village in the Cotswolds.
Total ascent: 405m / descent 400m
STANTON TO CLEEVE HILL (21KM)
Walk through lovely meadowland before passing the grand 16th-century Stanway House. It’s hidden from view behind golden stone walls, but famous for its stately Jacobean gatehouse. The path begins a steady climb with respite found at the wonderfully-named Pinky Dickins bench before following the escarpment to Beckbury Camp — an Iron Age hill fort. The trail passes the ruins of 13th-century Hailes Abbey. This was once a pilgrimage destination before being destroyed under the reign of Henry VIII. From here, descend into bustling Winchcombe and Sudeley Castle before the path rises on gentle trails to the highest point (325m) of the walk at Cleeve Hill Common. Here you can look out to the River Severn and Wales. You will also pass by Belas Knap, an interesting Neolithic ancient burial mound with four chambers. It’s a worthwhile place to take a break.
Total ascent: 575m / Descent 370m
CLEEVE HILL TO BIRDLIP (25KM)
The trail continues along the Cotswold escarpment with highlights including gorgeous views over spa town Cheltenham and beyond. Enjoy glorious woodland walking surrounded by bluebells, wild garlic and ancient beech trees. You will also find two designated reserves harbouring rare butterflies. Near Leckhampton, keep a lookout for the distinctive limestone rock formation known as the Devil’s Chimney. As you near Birdlip you’ll pass Crickley Hill and Barrow Wake, a ‘biological and geological Site of Special Scientific Interest‘, which embraces an abundance of orchids, flowers, herbs, butterflies, snails and moths.
Total ascent: 595m / descent 615m
BIRDLIP TO PAINSWICK (14KM)
The trail descends from Birdlip through beautiful beech woodlands before climbing to Coopers Hill. This hill is famous for its annual cheese-rolling event. Fun facts — the event dates back to the 1700s, and the cheese rolls down the hill at approximately 70kph. The path leads to Painswick Beacon where there are the remains of an Iron Age hill fort. Historic Painswick is often referred to as “The Queen of the Cotswolds”. This town is one of the best-preserved villages in the Cotswolds and famous for its Rococo Gardens and 99 yew trees surrounding St Mary’s church. According to legend, should a 100th tree grow, the Devil would pull it out.
Total ascent: 575m / descent 685m
Today your Cotswold Way adventure ends after breakfast. You may wish to consider extending your stay to further explore this charming area.
What you get
- 6 nights in quintessential Cotswold accommodation including small hotels and B&Bs
- Daily breakfast including fresh fruits, yoghurt, cereals and/or a hearty, cooked English breakfast to support your day on the trail
- Pack-free walking with luggage transfers on each hiking day (1 x 20kg bag per person)
- Comprehensive information pack including detailed walk notes, map, luggage tag and laptop case
- 24/7 support from our UK-based RAW Travel staff member
- Pre-trip guidance and planning from experienced and dedicated RAW Travel Destination Experts
- Hassle-free walking with exclusive use of RAW Travel’s specifically designed navigational hiking App
- Single supplement $550
- Travel insurance
- Lunch and dinners
The Self-Guided Walk – Cotswold Way
- Marvel at the fine Georgian architecture in World Heritage Bath
- Wander among age-old beech trees along quiet woodland trails
- Explore some of the worlds best-preserved ancient Roman baths
- Delight at the chocolate-box villages and picture-perfect countryside
South Cotswolds – Cotswold Way
- Walk from charming Painswick to the elegant streets of Bath
- Explore honey-coloured villages and medieval market towns
- Follow the path through two butterfly conservation reserves
- Discover the ancient history of Neolithic Belas Knap
The Self-Guided Walk – Hadrian’s Wall
- Marvel at 2,000 years of ancient Roman history
- Explore a ‘Frontiers of the Roman Empire’ World Heritage Site
- Enjoy Newcastles’ Victorian and post-industrial architecture
- Meander through idyllic countryside and picturesque villages
TRIP date selection
when would you like to travel?
Please select your preferred dates for on-demand trips or select a scheduled date for group departures. If you have booked a self-guided trip please understand that because your trip date is on demand and we must check availability of all properties on your chosen dates before it can be fully confirmed