If you ask any walker to sketch the skyline of the Shropshire Hills, they will likely draw the long, flat back of the Long Mynd. But if you ask those in the know which hill has the most character, the answer is almost always Caer Caradoc.
Sharply pointed, volcanic, and steeped in ancient legend, it screams for attention.
I headed out recently to tackle this icon on a circular loop that doesn’t just bag one peak, but two. I paired the dramatic Caradoc with its wilder, grassy neighbour, Hope Bowdler Hill.

It’s a route of contrasts: jagged rocks versus rolling moorland, lungs-burning climbs versus sweeping descents. And, in a twist I didn’t see coming, it features perhaps the greatest start/finish line feature in hiking history: a fully stocked, self-service farm vending machine.
- Distance: 6 miles (10 km)
- Ascent: 520 m (1,706 ft)
- Difficulty: Moderate
- Time: Allow 3–4 hours to soak in the views.
- Start: Near Gaerstone Farm (Church Stretton area).
- Postcode: SY6 7ES
- Refreshments: The Vending Hut at the start/finish!

Parking & Practicalities
The walk begins from the lane near Gaerstone Farm, just outside Church Stretton.
- Postcode: SY6 7ES
- Location: There is informal layby parking available near the farm entrance on the B4371.
- Note: This is a working farm area. Please ensure you park responsibly in the laybys and do not block any farm gates or machinery access.

The Walk Profile: A Tale of Two Hills
To give you an idea of what your legs are in for, here is how the walk breaks down based on the data:
- Start (258m): We began near Gaerstone Farm, already sitting at a decent height.
- The Big Climb (456m): The ascent to Caer Caradoc is the toughest part of the day. You gain nearly 200m in elevation in a short, sharp burst to reach the Iron Age fort.
- The Drop (200m): What goes up must come down—steeply! After the first hill you head down sharply.
- The Second Rise (422m): The climb back up to Hope Bowdler Hill is a steady pull back up to the ridge.
- The Finish (256m): A gentle descent back to the farm (and the milkshakes).
The Sharp Ascent: Caer Caradoc
I started the walk from the tracks near Gaerstone Farm. There is no gentle warm-up on this route; the presence of Caer Caradoc looms over you immediately.
The name “Caer” implies a fortress, and as you start the ascent, you can see why. The hill rises abruptly from the valley floor.
The path winds upwards, and the elevation gain is serious right from the off. It’s a “hands on knees” sort of climb in places, but the distraction is the landscape unfolding behind you.

As you gain height, the town of Church Stretton shrinks into a miniature village, and the massive bulk of the Long Mynd dominates the western horizon.
Near the top, keep an eye out for Three Fingers Rock, a jagged volcanic outcrop that looks exactly like a hand reaching out of the earth.

King of the Castle
Reaching the summit of Caradoc feels like a genuine achievement. The top is crowned by the deep ditches and ramparts of an Ancient British Iron Age hillfort.
Legend tells that this was the site of the last stand of Caratacus, the British chieftain who defied the Roman Empire.
Standing on the wind-battered summit, looking out over 360 degrees of English and Welsh countryside, it feels like a place for heroes. It is rugged, rocky, and undeniably dramatic.

The Second Peak: Hope Bowdler Hill
Leaving the fortress behind, we dropped steeply down the opposite side. This section gives the legs a brief respite as you descend into the green valley floor at around 200m elevation.
Look ahead and you get an amazing view to another icon of a hill, The Wrekin.

Before you swing back and head towards the second hill you wander along some gorgeously tree lined lanes, it looked great in Springtime bloom, but this is a great walk for any season.

But, as they say, what goes down must come up.
The climb up Hope Bowdler Hill has a completely different personality. Where Caradoc is jagged and brooding, Hope Bowdler feels wilder and more open. It’s a grassy, broad-backed ridge that feels less like a fortress and more like high moorland.

Navigating through the “Battlestones” area, the walking here is joyous. You are high up (peaking at 422m), with the wind in your face and the hard work mostly behind you.

The views back toward the profile of Caradoc are spectacular—it’s the best vantage point to appreciate the cone shape of the hill you just conquered.
The Ultimate Finish
The descent from Hope Bowdler gently winds you back down towards the valley floor, eventually looping us back toward our starting point at Gaerstone Farm.
Usually, the end of a walk involves a muddy changing of boots and a hunt for a car key. Not here.
Waiting for us at the farm was The Vending Hut.

This isn’t a rusty old machine dispensing warm cola. This is a pristine, timber-clad room housing high-tech vending machines filled with local delights.
We’re talking fresh, chilled milkshakes (in glass bottles!), cold soft drinks, local cheeses, and snacks.
There is something surreal and wonderful about coming off a rugged, prehistoric landscape and immediately being able to buy a fresh, ice-cold milkshake from a robot on a farm.
It was the absolute perfect way to cool down and toast a brilliant few hours in the hills.
If you love a walk that rewards you twice—once with views, and once with dairy—this is the one for you.

















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