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Challenge walks in Oxfordshire

Find challenge walks near me in Oxfordshire for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.

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Events near me

Click an event for full event details, location, route, sustainability, what's included and how to enter.

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Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming walking adventure.
  • Sat 10 May
  • £25
  • Entries close soon
  • Sat 10 May
  • £25
  • Entries close soon
Woodstock, Oxfordshire, UK

Pink Ribbon Walk | Blenheim Palace and the Cotswolds | 20 Mile

Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming walking adventure.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 20 miles walking
Entries closed
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
  • Sat 19 Jul
  • £25
  • Entries closed
  • Sat 19 Jul
  • £25
  • Entries closed
Woodstock, Oxfordshire, UK

Mighty Hikes | Cotswolds | Marathon

Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 25.24 miles hiking + 452.61 m ascent
Entries closed
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
  • Sat 19 Jul
  • £20
  • Entries closed
  • Sat 19 Jul
  • £20
  • Entries closed
Chipping Norton, Oxfordshire, UK

Mighty Hikes | Cotswolds | Half Marathon

Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.38 miles hiking + 285.55 m ascent
The full 50K route of the Chiltern 50 Ultra Challenge starts from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village to a party finish!
  • Sat 27 Sep
  • £139
  • 13 charities
  • Sat 27 Sep
  • £139
  • 13 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Ultra Challenge | Full 50km

The full 50K route of the Chiltern 50 Ultra Challenge starts from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village to a party finish!

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 50 km trail running + 920 m ascent
An exciting 25km loop as part of the Chiltern 50 Ultra Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village to a celebratory finish!
  • Sat 27 Sep
  • £89
  • 13 charities
  • Sat 27 Sep
  • £89
  • 13 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Ultra Challenge | Henley 25km Loop

An exciting 25km loop as part of the Chiltern 50 Ultra Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village to a celebratory finish!

  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent

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