Danny Mason Highlands Challenge

(formerly “Shropshire Highlands Challenge”)

Sunday 9th June 2019

A challenging 66 mile ride at your own pace all on quiet roads and lanes in the beautiful border hills of the Marches. Not a “pretend” road race – no tags, timings or numbers – how you ride is up to you. A great but tough day among Shropshire’s “Blue Remembered Hills” and the quiet leafy lanes of Herefordshire and Powys.
Now in its twenty-eighth year.
After running costs, all proceeds go to MacMillan Cancer Support.

Enter early – the event has a rider limit which has been reached in previous years.

Make it a weekend if you wish in Ludlow town. Excellent secluded camping and caravan facilities at event H.Q. below the castle.


The Highlands Challenge is famous for its catering.

Breakfast Bargain

Sausage or bacon baps, tea and coffee available before the start. Modest prices! Ideal for camping without chores or if you are travelling a long distance to the event.

Morning refreshment stop

Complimentary tea, coffee and cakes.


Large filled rolls, crisps, cakes, tea and coffee at modest prices.

Afternoon refreshment stop

Complimentary tea, coffee and cakes.

Organised by Ludlow Cycling Club and Ludlow Cycling Festival