Panoramic view from a hill on Cotswold Way south of Winchcombe, Cheltenham, UK overlooking the hilly agricultural landscape with large green tree standing alone in middle against a blue sky
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Walking Holidays and Outdoor Adventures in Winchcombe

Walkers-welcome town, castle gardens, and crossroads of Cotswold trails

Where honey-stone lanes meet rolling escarpments — and every route tells a story.

Winchcombe is an ideal base for walking holidays and outdoor adventures in the North Cotswolds. The Cotswold Way runs through town, while local classics radiate in every direction: the figure-of-eight Winchcombe Way, hilltop views to Belas Knap Long Barrow, quiet paths to Hailes Abbey, and charming village links toward Stanway and Stanton. You can also connect via the Wardens Way and Windrush Way between Winchcombe and Bourton-on-the-Water, or follow the Isbourne Way to Evesham.

Between walks, explore Sudeley Castle & Gardens, browse independent shops, and settle into pubs and cafés that make Winchcombe a true walkers’ town.

Why Walk Here

Nearby Trails

Outdoor Adventures and Activities

Frequently Asked Questions

Can I start a self-guided walking holiday from Winchcombe?

Yes — Winchcombe sits on the Cotswold Way and anchors the Winchcombe Way, with straightforward links to Belas Knap, Hailes Abbey, and nearby villages for multi-day itineraries.

Where should walkers stay in Winchcombe?

Expect walker-friendly inns, boutique B&Bs, and self-catering cottages in and around the town, many within a short stroll of trailheads.

Is Winchcombe good for a car-free walking break?

Definitely — frequent buses connect via Cheltenham and Broadway; the Gloucestershire Warwickshire Steam Railway (seasonal) stops nearby for heritage links. Many walks start right from the High Street.

What’s a great first-day or rest-day walk?

Try the Hailes Abbey loop for a gentle warm-up, or the Belas Knap circuit for classic escarpment views. For a village day, walk the Stanway–Stanton section and return.

When’s the best time to visit Winchcombe for walking?

Spring brings wildflowers to the meadows, summer offers long days and clear escarpment views, autumn brings golden foliage, and winter walks can be crisp and quiet with fewer visitors.

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