Challenge walks in May 2026
Find challenge walks in May 2026 - filter by date or location, display on a map or use the advanced search to find your perfect race.
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- Sat 9 - Sun 10 May 2026
- £95.50-£155.50
24 Hours South | The Offa's Dyke Ultra
The finish line is unique to you: 24 hours after the mass start, the race shall stop and the Solo Runners and Teams furthest South on the National Trail, shall be declared winners.
- Newcomers
- Chip timing
- Enter online
- GPS tracking
- Event village
- Rural
- Age 18 & over
- 24 hrs trail running + 8561 ft ascent
- Fri 15 - Sun 17 May 2026
- £350
Incredible Hike
The ultimate coast path challenge! Walk 60 miles of the South West Coast Path over 3 days and take in the breathtaking sights and soak up the camaraderie for Children’s Hospice South West.
- Fundraising required
- Undulating
- Hilly
- Traffic free
- Rural
- Coast
- Age 18 & over
- 60 miles hiking
- Sat 16 May 2026
- £30-£55
Keswick Mountain Festival 3 Peaks
A mid-level, circular hike over the three peaks surrounding Derwentwater Catbells, Walla Crag and Latrigg. Includes Full Weekend Festival Ticket in the price!
- Families
- Newcomers
- Music
- Chip timing
- Mountainous
- Event village
- Age 12 & over
- 18 miles hiking + 1050 m ascent
- Sat 16 - Sun 17 May 2026
- £20
Follow the Seagulls | Isle of Wight | One Day Challenge
A trekking challenge on Saturday OR Sunday along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust.
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 25 miles walking
- Sat 16 - Sun 17 May 2026
- £30
Follow the Seagulls | Isle of Wight | Two Day Challenge
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 50 miles walking
- Sun 17 May 2026
- £65
Keswick Mountain Festival 8 Peaks
A high-level horseshoe walk on varied terrain around the stunning fells surrounding Derwentwater and the Borrowdale Valley for experienced hikers. Includes Full Weekend Festival Ticket in the price!
- Newcomers
- Music
- Chip timing
- Mountainous
- Event village
- Age 18 & over
- 18 miles hiking + 1350 m ascent
- Sat 30 May 2026
- £30
Lake District Running Festival | Grasmere Gallop Nordic Walking Challenge
The 10km Nordic Walk takes a scenic route through some classic Lake District Landscapes, including the shores of Grasmere and Rydal, as you propel yourself along with your poles.
- Undulating
- Age 15 & over
- 10 km walking + 160 m ascent