(formerly “Shropshire Highlands Challenge”)
Sunday June 14 2026
Entries will open in late 2025
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For 35 years, hundreds of folk who love riding their bikes descend on Ludlow Castle to tackle a uniquely friendly and iconic ride through the beautiful Shropshire Hills National Landscape.
Founded and organised by Danny Mason for 25 years, the Highland Challenge is now organised by volunteers from Ludlow Cycling Club, and registered with Cycling UK.
350 riders entered the 34th Highland Challenge in June 2025 and enjoyed another great day out.
Approximately 66 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 limited road signage: you can either download the route in advance onto your GPS device or print out the map and route card to take with you.
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.
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 £10
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
