Winchcombe is a Cotswold town with timbered inns, quality shops, centuries-old architecture and stunning countryside offering beautiful walks, and a castle!
There are 12 routes to explore the Cotswolds from Winchcombe
Upland walk around the source of the River Coln
An upland walk from Wardens’ Wood around the headwaters of the river Coln and includes the villages of Sevenhampton and Brockhampton.
Cheltenham
- Length
- 5.5 miles
- Difficulty
- Moderate
Walking the Ways 2 (of 5)
The second of five circular walks during the year exploring the Wardens’ and Windrush Ways. Each is a complete walk, so no need to commit to them all. The Ways run between Winchcombe and Bourton on the Water.
Bourton-on-the-water
- Length
- 9 miles
- Difficulty
- Moderate
Walking the Ways 1 (of 5)
The first of five circular walks during 2025 exploring the Wardens' and Windrush Ways, which run between Winchcombe and Bourton on the Water, and the landscape and villages they pass through.
Bourton-on-the-water
- Length
- 8.5 miles
- Difficulty
- Moderate
Walking the Ways 5 (of 5)
The last in a series of circular walks exploring the Wardens’ and Windrush Ways, which both end in Bourton. On this walk we go to Lower Slaughter on the Windrush Way, before returning to Bourton on the Wardens’ Way. We then explore to the east of Bourton using the Oxfordshire Way.
Bourton-on-the-water
- Length
- 9 miles
- Difficulty
- Moderate
Walking the Ways 3 (of 5)
The third in a series of circular walks exploring the Wardens’ and Windrush Ways, which follow different routes between Winchcombe and Bourton on the Water. Each is a complete walk, so no need to commit to them all.
Bourton-on-the-water
- Length
- 8 miles
- Difficulty
- Moderate
Kilkenny Views (we hope)
Starting in public car park (free) we go past St Paul's Epistle, descend to Foxcote, make our way to Shill Hill and back across the escarpment (hopefully with views!)
Cheltenham
- Length
- 5.5 miles
- Difficulty
- Moderate
Andoversford - Miles without Stiles
This walk links Andoversford, Sevenhampton and Brockhampton with interesting features along the way and beautiful views of the Coln Valley.
Bourton-on-the-water
- Length
- 5 miles
- Difficulty
- Easy
- Mobility aid rating
- Stile free
Wild Wintry Wolds - binoculars essential
A return to explore of the fields and woods above Stanton, searching for wintering birds. The route will depend on what we find but is approximately 4 - 6 miles in length. There are some steep slopes and paths will be muddy so wear appropriate footwear!
Bourton-on-the-water
- Length
- 5 miles
- Difficulty
- Moderate
Naunton to Guiting Power
Two Cotswold villages along the Windrush Valley. Starting from one pub and a church, we cross fields along the valley from one to the other and then take a higher route back.
Bourton-on-the-water
- Length
- 6 miles
- Difficulty
- Moderate
Stanton to Stanway via the Cotswold Edge
From Stanton we have a 600ft (200m) steep climb up to the Cotswold Edge, then continue, with views across the vale to the west. We descend down to Stanway and have a gentle stroll across fields back to the start.
Broadway
- Length
- 5 miles
- Difficulty
- Moderate
Ford to Cutsdean and a visit to Jackdaws Castle
A circular walk from Ford to Cutsdean. We then carry on to join the Diamond Way and back through Jackdaws Castle, one of the finest training facilities in British jump racing. Please bring drink/snack.
Stow-on-the-wold
- Length
- 5.5 miles
- Difficulty
- Moderate
In search of Dreghorn. A riot, Piccadilly and a Devil’s Chimney!
The route starts in Daisybank CP , climbs the old tramway incline to the foot of Dreghorn's famous limestone rock formation. then it follows the track up past Deadman's quarry and the Devil's Chimney, then it goes up to the Hillfort across to the trig point.
Cheltenham
- Length
- 4 miles
- Difficulty
- Moderate