Weekender: Hell of the Ashdown

Route name: Hell of the Ashdown
Start/finish: Westerham Brewery, Westerham, Kent
Maps: OS Landrangers 198 (Tunbridge Wells & East Grinstead) and 188 (Maidstone & The Weald)
Ride length: 93.29km (58 miles)
Climbing: 1,674 metres
Bike type: Road bike (lower gearing recommended)
Ride level: Experienced

The Hell of the Ashdown is a ride that quietly earns its name. At just over 93km it doesn’t appear intimidating, yet the amount of climbing (1,674 metres) packed into that distance tells a different story.

There are no mountain passes here, just a steady succession of short, sharp Weald gradients. Moreover, the annual sportive that I rode is in February. Spring or summer would be a less gruelling day out if you’re riding the route independently.

Starting from Westerham Brewery, the loop runs anticlockwise into the rolling folds of the High Weald. The opening kilometres offer little time to warm up before Toys Hill sets the tone: a 2.9km climb averaging 6%, with some steeper sections.

From there, narrow lanes thread south through hedge-lined countryside and wooded hollows, rising and dipping with enough frequency to prevent any prolonged stretch of ease. Just as the rhythm settles, it changes.

It doesn’t appear intimidating, yet the amount of climbing (1,674 metres) packed into that distance tells a different story Stephanie Rukin

The route passes near Hever Castle, childhood home of Anne Boleyn, its Tudor brickwork providing a brief visual pause before the climbing resumes. Priory Road and Twyford Lane sharpen the legs, each ramp arriving without ceremony.

Then comes Kidd’s Hill – known locally as The Wall – a climb that builds in stages and resists any attempt at comfortable pacing. It isn’t especially long, but it commands attention.

As the loop begins to arc back north-west, Bayley’s Hill offers another stern test. By now, effort management earlier in the ride starts to feel significant. Beyond, the landscape opens towards the higher ground near Ashdown Forest.

A short, optional detour into Hartfield adds extra elevation but rewards with sweeping views towards the South Downs, the pale chalk ridge standing clear on bright days. A pause at the village’s Winnie-the-Pooh café provides welcome encouragement before the final miles back towards Westerham.

The sportive route is adjusted slightly from year to year to reflect road surface conditions, so exact figures can vary. The character, however, remains constant: quiet rural lanes, persistent gradients and scenery that more than justifies the effort.

As you finish back at the brewery, there is a real sense of achievement – not from conquering one monumental climb but from having met them all.

1. Toys Hill

A steady opening test up the densely wooded Greensand Ridge, Toys Hill encourages restraint rather than bravado. Long enough to sting at 1.8 miles, it is consistent enough to ride at tempo, with an average gradient of 6%. Toys Hill sets the pattern for the day, so pace it sensibly. There is plenty more to come.

2. Hever Castle

The route passes close to Hever Castle, childhood home of Anne Boleyn – Henry VIII’s second wife. Tudor brickwork and manicured grounds contrast with the steep, narrow lanes nearby. It’s a brief historical interlude before the gradients reassert themselves. If you’re riding the route casually, you could pay a visit. There are bike racks at the entrance.

3. Priory Road

Leaving Forest Row, a village ranked as Britain’s third poshest by Country Living magazine, Priory Road is a short climb that’s enclosed by woodland. It ramps up quickly, with a gradient that feels steeper than the route profile suggests. Smooth, seated climbing pays dividends.

4. Hartfield detour

If you’re riding the route independently and want a short diversion before tackling Kidd’s Hill, head to Hartfield. While it means more climbing, you’re rewarded with expansive views towards the South Downs. Pooh Corner, a tearoom, gift shop and museum celebrating AA Milne’s fictional bear, is a good place to refuel. Honey optional.

5. Kidd’s Hill

Known locally as The Wall, Kidd’s Hill starts from Coleman’s Hatch and heads straight uphill, with no hairpins to hide what’s ahead. It builds in stages, which makes rhythm difficult to find. It isn’t excessively long, but has a maximum gradient of 16%. It demands steady pacing and sensible gearing.

6. Bayley’s Hill

Arriving later in the loop, just after Sevenoaks Weald, Bayley’s Hill tests whatever reserves you have left. It twists between hedgerows that mask its summit, so it feels longer than the official length of 1.3km. If you have the energy to look up, the views over your shoulder are well worth it.