Find challenge walks near me in South East 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.
Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.
Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.
The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.
An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.
The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.
A NEW looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’.
Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.
Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.
Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area.
Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.
Help transform the future of breast cancer one step at a time at this iconic venue where you'll walk through beautiful woods and fields on a ramble-ready route then receive your medal!
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!
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!
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
Starting at Oaks Park then following the fantastic 2nd 1/4 Challenge route to Tulley’s Farm in Turners Hill, and then on over the South Downs & the finish line at Brighton Racecourse.
A great challenge through the Surrey & Sussex countryside – with a Sutton start and Turners Hill / Tulley’s Farm finish.
A new 25 km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the south Downs Way with its fabulous views back over the Sussex countryside.
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
Now in its 17th year, this wonderfully popular walk takes you off the beaten track through some of Hampshire and Wiltshire's most beautiful countryside to support two local hospices.
Join a mid-summer North Downs 50 Challenge! This looped route is set in an area of outstanding natural beauty of the Surrey Hills, taking in chalk ridges and ancient woodlands.
The 25km looped challenge sets out from Guildford early Saturday morning, along some of the most picturesque parts of the Surrey Hills Way – with a rest stop at half way with snacks and drinks.
Follow the North Downs Way to Dorking for a 24km challenge with fabulous views. You’ll get full support all the way, rest stops en route and a picnic lunch at the finish.
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.