Cotswolds Midweek Guided Walking Holiday

Explore England's Most Beautiful Countryside

The Cotswolds National Landscape offers some of Britain's most enchanting walking, from rolling hills dotted with honey-coloured stone villages to ancient trails steeped in history. This midweek walking holiday combines the very best Cotswolds walks with a comfortable base in Chipping Norton, giving you easy access to excellent evening dining and the town's welcoming atmosphere.

Our leisurely-paced Cotswolds walking holiday takes you to iconic locations like Stow-on-the-Wold, Lower Slaughter, and Bourton-on-the-Water (the 'Venice of the Cotswolds'), plus the mystical Rollright Stones and Broadway Tower. You'll discover Shakespeare's Way, ancient trading routes, and some of England's most photographed villages.

Perfect for solo travellers and small groups, this Cotswolds walking break offers stunning countryside scenery, fascinating local history, and the chance to explore England's most beloved landscape with expert local guides. With all transport included from your Chipping Norton hotel, you can focus entirely on enjoying the walks, the company, and the timeless Cotswolds charm.

Suggested Itinerary

Here’s what we’ve got planned - of course, we may have to offer alternatives or make amendments if the weather misbehaves or other unexpected situations arise!

Day 1 - Arrival & Welcome

Arrive at the Premier Inn Chipping Norton from 15:00 and settle into your room in this historic market town. The hotel puts you right in the heart of the action, with independent shops, cosy cafés, and traditional pubs all within easy walking distance.

Your friendly host will meet everyone in the hotel bar from 18:00, where you'll get to know your fellow walkers over drinks before heading out for dinner together. Evening meals are not included, giving you the freedom to explore Chipping Norton's excellent pub and restaurant scene.

Day 2 - Stow-on-the-Wold & Cotswolds Villages

After a hearty cooked breakfast, we'll drive to the picturesque village of Stow-on-the-Wold for our first Cotswolds adventure. This spectacular walk takes you through some of the must-see places in the Cotswolds, following sections of The Monarch's Way long-distance path.

We'll visit Lower Slaughter, often called one of England's most beautiful villages, before continuing through lovely riverside surroundings to Bourton-on-the-Water, known as the 'Venice of the Cotswolds' thanks to the River Windrush flowing gently through the village centre. We'll enjoy a café stop in Bourton to soak up the scenery before picking up the Diamond Way path to Icomb and returning to Stow-on-the-Wold. Before heading back, we may visit one of Stow's wonderful pubs to savour the day with a drink in hand.

Day 3 - Broadway Tower & Cotswolds Escarpment

Today we explore the dramatic Cotswolds escarpment and visit the iconic Broadway Tower, one of the area's most recognisable landmarks. This folly tower, built in 1798, offers spectacular panoramic views across multiple counties on clear days. Our walk takes us through the picturesque village of Broadway, often called the 'Jewel of the Cotswolds', with its wide main street lined with honey-coloured cottages and boutique shops.

We'll explore the surrounding countryside, walking ancient paths through beech woodlands and across open hilltops with sweeping views over the Vale of Evesham. The contrast between the intimate village streets and the expansive countryside views makes this a truly memorable day's walking.

Day 4 - Shakespeare's Way & The Rollright Stones

Our final morning takes us along Shakespeare's Way, a historic route linking Stratford-upon-Avon with London, said to have been used by the playwright himself. The highlight is visiting the mysterious Rollright Stones - a 4,000-year-old Neolithic stone circle steeped in folklore, plus the Whispering Knights burial chamber and the solitary King's Stone, all tied to local legends.

After completing our loop and exploring these ancient mysteries, we'll return to Chipping Norton for a final group lunch at a local café or pub before saying our goodbyes.