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Challenge walks in Gloucestershire

Find challenge walks near me in Gloucestershire for 2024/2025 - search by date or place, display on a map or use the advanced search to find your perfect race.

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The second half option of the Thames Path Challenge from Runnymede along the meandering river through Cookham to Henley-on-Thames, home of the regatta, to a celebration finish and family BBQ.
  • Sat 21 Jun 2025
  • 12 charities
  • Sat 21 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | 1st Half charity places

The second half option of the Thames Path Challenge from Runnymede along the meandering river through Cookham to Henley-on-Thames, home of the regatta, to a celebration finish and family BBQ.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 53 km trail running + 1600 m ascent
Take on a 100km challenge, making a fully supported loop from Cirencester, exploring the picturesque, undulating terrain of the Cotswolds on a spectacular challenge.
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | Full 100km continuous charity places

Take on a 100km challenge, making a fully supported loop from Cirencester, exploring the picturesque, undulating terrain of the Cotswolds on a spectacular challenge.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 2250 m ascent
Walk, jog or run the full 100km challenge, split over two days, with a well deserved nights sleep at the half way basecamp, to recharge your batteries overnight.
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | Full 100km over 2 days charity places

Walk, jog or run the full 100km challenge, split over two days, with a well deserved nights sleep at the half way basecamp, to recharge your batteries overnight.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 2250 m ascent
Take on the rolling undulations of the Cotswold Way, departing from Cirencester to explore the beautiful landscapes of the first section of the 100km route.
  • Sat 21 Jun 2025
  • 12 charities
  • Sat 21 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | 1st Quarter charity places

Take on the rolling undulations of the Cotswold Way, departing from Cirencester to explore the beautiful landscapes of the first section of the 100km route.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 23 km trail running + 600 m ascent
Explore the most scenic stretch of the Cotswold way, with the challenging route making you work hard for those sublime views.
  • Sat 21 Jun 2025
  • 12 charities
  • Sat 21 Jun 2025
  • 12 charities
Stroud, Gloucestershire, UK

Cotswold Way Ultra Challenge | 2nd Quarter charity places

Explore the most scenic stretch of the Cotswold way, with the challenging route making you work hard for those sublime views.

  • Chip timing
  • Enter online
  • GPS tracking
  • Age 14 & over
  • 30 km trail running + 1000 m ascent
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.
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | 3/4 Challenge charity places

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.

  • Chip timing
  • Enter online
  • GPS tracking
  • Age 18 & over
  • 76 km trail running + 1650 m ascent
Take on a gently undulating route, departing either on Saturday evening or Sunday morning, to explore the beautiful route between Wotton and Cirencester.
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
  • Sat 21 - Sun 22 Jun 2025
  • 12 charities
Cirencester, Gloucestershire, UK

Cotswold Way Ultra Challenge | 2nd Half charity places

Take on a gently undulating route, departing either on Saturday evening or Sunday morning, to explore the beautiful route between Wotton and Cirencester.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 47 km trail running + 650 m ascent
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.
  • Sat 12 Jul 2025
  • £25
  • Sat 12 Jul 2025
  • £25
Moreton-in-Marsh, Gloucestershire, UK

Big Hike | Cotswolds | Marathon

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.

  • Chip timing
  • Enter online
  • Fundraising required
  • Hilly
  • Age 16 & over
  • 26.2 miles hiking + 1900 ft ascent
Hike through rolling hills and picturesque villages of the Cotswolds, including Aston Magna, Paxford and Ebrington, to help beat cancer step by step.
  • Sat 12 Jul 2025
  • £20
  • Sat 12 Jul 2025
  • £20
Moreton-in-Marsh, Gloucestershire, UK

Big Hike | Cotswolds | Half Marathon

Hike through rolling hills and picturesque villages of the Cotswolds, including Aston Magna, Paxford and Ebrington, to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.1 miles hiking + 1200 ft ascent

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