(formerly “Shropshire Highlands Challenge”)
We are sad to report that Danny Mason, founder of the Highland Challenge and its organiser for the first 25 years, passed away in July 2026, four months short of his 100th birthday
The 2026 edition of the Danny Mason Highland Challenge was held on
Sunday June 14 2026
The next edition will be held on
Sunday June 6th 2027
The event will open for entries before Christmas 2026
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For 35 years, hundreds of folk who love riding their bikes have gathered underneath Ludlow Castle in June to tackle a uniquely friendly and iconic ride through the beautiful Shropshire Hills National Landscape.
Founded and then organised by Danny Mason for 25 years, the Highland Challenge is now organised by volunteers from Ludlow Cycling Club, and registered with Cycling UK.
Around 350 riders entered the 34th Highland Challenge in June 2026 and enjoyed another great day out.
Approximately 68 hilly miles, with a new route each year.
The Highland Challenge isn’t a race – no tags, timings or numbers – how you ride is up to you. It normally attracts both young fast club riders and older once-a-year tourers – and everything in between!
With around 1,650m (5,400ft) of climbing and some challenging lanes in the rural corners of Shropshire, to complete it you’ll need some strength, stamina, bike handling ability and to be reasonably fit.
There is now road signage at junctions and turnings on the route, but you can also download the route in advance onto your GPS device.
It’s a great but tough day for all types. There are toilets and refreshments at the start and at three refreshment stops en-route, all included in the fee.
After costs, all proceeds from the event go to Shropshire Wildlife Trust, who do so much to look after the beauty and wildlife of the terrain we ride through. The Challenge has raised around £27,000 for SWT over the last six years.
NEW SINCE 2025:
A family-friendly approximately 20 mile/30km gentle Sunday morning “LOWLAND CHALLENGE” option, from and back to Ludlow Rugby Club.
Be part of the day but miss out 80% of the climbing!
Only £12.50
http://www.shropshirehighlandchallenge.co.uk/lowland-challenge/
Do you want to go the extra mile for nature?
You can further support Shropshire Wildlife Trust by setting up a JustGiving page and getting sponsored to participate in this event: https://www.justgiving.com/shropshire-wildlife
If you have any questions about fundraising for Shropshire Wildlife Trust, please contact: wendyw@shropshirewildlifetrust.org.uk
