Find challenge walks near me in Gloucestershire for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.
Click an event for full event details, location, route, sustainability, what's included and how to enter.
The first half of the challenge is tough with steep ascents and descents taking you into the heart of this beautiful landscape with magnificent views out to the West.
Head into the rolling green hills of the Cotswolds with leg-testing climbs and breathtaking views on your 100km mission, with stops every 12-13km and a halfway break in Wotton, you're fully supported.
Head into the rolling green hills of the Cotswolds with leg-testing climbs and breathtaking views on your 100km mission in daylight only with the benefit of a mid-way break and good night's sleep.
The 1st Quarter of the Cotswold Way Challenge will start from Cirencester basecamp. It's tough with some steep ascents and descents taking you into the heart of this beautiful landscape.
Arguably the most scenic stretch of the whole Cotswold Way route. Head towards Coaley Peak with its breathtaking views over the Severne Valley, to Wotton-Under-Edge for a celebration and hot meal!
The route is 3/4 of the full challenge – so starts at Painswick, takes in the fantastic 2nd 1/4 Challenge route to Wotton, and then on through the Cotswolds to the finish line at Cirencester basecamp.
A start at Wotton and then some fantastic Cotswold scenery in the heart of this beautiful landscape, on the way back to the very welcome finish line celebration back at Cirencester basecamp.
Hike through the rolling hills and picturesque villages of the Cotswolds. Walk right past Broadway Tower and take in stunning views from Dover’s Hill to help beat cancer step by step.
Hike through rolling hills and picturesque villages of the Cotswolds, including Aston Magna, Paxford and Ebrington, to help beat cancer step by step.