Sunday 13th December
The Chilly Hilly 2026
West Wight Sports & Community Centre
Big hills. Big achievement. Big community spirit.
The Chilly Hilly is one of the Isle of Wight's most popular winter running events, offering a unique off-road challenge through the stunning landscapes of West Wight.
Supporting the West Wight Sports & Community Centre Trust (registered charity number 273334).
Known for its challenging hills, muddy trails and spectacular views, this friendly and welcoming event attracts runners from across the Isle of Wight and beyond. Whether you're chasing a personal best, training for a bigger challenge or simply looking for a memorable running experience, The Chilly Hilly provides the perfect opportunity to test yourself while supporting a local charity.
Organised in support of West Wight Sports and Community Centre, the event helps raise vital funds that support community health, well-being and activity across West Wight.
What is the The Chilly Hilly?
The Chilly Hilly is a spectacular 10-mile cross-country race through some of the most beautiful and varied landscapes in West Wight.
The route takes runners across downs, cliff tops, marshes, fields, footpaths and countryside trails, offering stunning views of the Needles, the West Wight coastline and the surrounding countryside.
With a mixture of terrain, challenging climbs and—more often than not—a healthy dose of mud and classic December weather, The Chilly Hilly is a rewarding test of endurance and determination.
Participants can expect:
- Challenging hills and varied terrain
- Stunning views of the Needles and West Wight coastline
- Downs, cliff tops, marshes, fields and countryside trails
- A friendly and supportive atmosphere
- Excellent marshals and event support
- A rewarding finish and sense of achievement
Whether you're a seasoned trail runner or taking on the challenge for the first time, you'll be supported every step of the way by our fantastic team of volunteers and marshals.
Why Take Part?
Challenge Yourself
Whether you're an experienced runner or simply looking for your next goal, The Chilly Hilly offers a rewarding challenge that will test both fitness and determination.
Experience West Wight
The event showcases some of the area's most beautiful countryside, combining fresh air, stunning views and a memorable route.
Support Your Community
Every entry helps support West Wight Sports and Community Centre, enabling us to continue providing activities, facilities and community support for people across West Wight.
Be Part of Something Special
The Chilly Hilly has built a loyal following over the years and remains a highlight of the local running calendar, bringing together runners, volunteers and supporters in a fantastic community atmosphere.
Event Information
Distance
- Approximately 10 miles
Terrain
- Cross-country
- Trails
- Fields
- Woodland paths
- Uneven ground
Suitable For
- Experienced runners
- Trail runners
- Club runners
- Those looking for a new endurance challenge
Volunteers
Events like The Chilly Hilly would not be possible without the support of volunteers.
From marshalling the course and helping with registration to supporting participants on the day, volunteers play a vital role in making the event a success.
If you'd like to volunteer at a future event, we'd love to hear from you.