Route Book › Challenging

Challenging Cycling Routes

Our most challenging cycling routes from London, built and ridden by London Dynamo members for club rides and race training. Expect long distances, big climbing days and steep ramps, for riders who want a serious training ride.

Every route here carries a Challenging Terrain label, whether from long distance, sustained climbing or steep ramps. Ride leaders can use this page to find the right route for a strong group. We recommend that every rider loads the route onto their Garmin or Wahoo bike computer.

Each route has a GPX file, an interactive map, an elevation profile, distance and climbing figures, a Terrain label from flat to challenging, and cafe stops where we have them, so you can match a route to the group and the day.

Ride at your own risk

The routes in this Route Book have been researched with the intention that they are suitable for cycling, but not all routes have been physically road-tested. Even routes that have been ridden may contain hazards, including potholes, loose chippings, poor road surfaces, steep descents and unforeseen dangers. Road and traffic conditions can change at any time. Anyone choosing to ride a route from this Route Book does so entirely at their own risk and is responsible for assessing whether the route and conditions are suitable for them.

  • Kent

Chartwell Loop

  • 74.9km
  • 1092m
Loops around Churchill's home at Chartwell and back over Toys Hill, with Brasted Hill adding some spice on the return.
Route
  • Gravel

Surrey Trails & Hills Gravel

  • 78.4km
  • 1,152m
A gravel loop through the Box Hill area, then on to Ranmore Common, White Downs and Effingham Forest.
Route
  • Surrey Hills

The Barhatch Blinder

  • 78.7km
  • 1,040m
A four-hill Surrey Hills route over Staple Lane, Row Lane, Barhatch Lane and Whitedown Lane, with some very steep ramps.
Route
  • Surrey Hills

Classic Surrey Hills – Long

  • 87.8km
  • 1,225m
The other classic London Dynamo ride: five notable climbs from Staple Lane to Box Hill, via Peaslake Lane, Leith Hill and Ranmore Common.
Route
  • Kent

Bayley’s Hill Loop

  • 93.4km
  • 1331m
An alternative way out of London via Beulah Hill, down to Chiddingstone by Hosey Hill and a long, picturesque climb of Bayley's Hill.
Route
  • Kent

The Kent Ramp Hunter

  • 94.8km
  • 1,481m
A relatively short but very challenging ride that takes on some of the steepest climbs in the area, including Downe Road and Toys Hill.
Route
  • Kent

Bough Beech Loop

  • 94.8km
  • 1332m
Crosses two ridges of the Downs to Chiddingstone, then returns past Bough Beech reservoir and up Ide Hill for the views.
Route
  • Kent

Hever Loop

  • 99.5km
  • 1402m
A tougher alternative to the Bough Beech route, taking Ide Hill south, looping round Hever Castle and climbing Toys Hill from the north.
Route
  • Kent

Kingdom Loop

  • 100.8km
  • 1435m
Heads south beyond Chiddingstone to Kingdom Café at Penshurst, then returns over Ide Hill and Brasted Hill.
Route
  • Kent

North Kent Woods & Downs

  • 113km
  • 1481m
Out into Dickens country across the Downs and woods of North Kent, with the climbing early and a café stop in Trosley Country Park.
Route
  • Gravel

Chartwell Gravel Loop

  • 120km
  • 1,809m
A largely off-road ride from Hampton Court into Kent to Churchill’s family home at Chartwell, returning through the woods of Toys Hill.
Route
  • Surrey Hills

Nove Colli di Surrey

  • 122.8km
  • 1,872m
A collect-the-set route through the Surrey Hills that takes in eight significant climbs, from Ranmore and Box Hill to Leith Hill and Combe Lane.
Route
  • One Way

London to Whitstable

  • 124.6km
  • 1,498m
A one-way ride south over Crystal Palace and Biggin Hill, then along the Pilgrim’s Way through the heart of Kent to the coast at Whitstable.
Route
  • Kent

The Kentish Kraken

  • 126km
  • 1,761m
A ride that winds across two ridges of the Downs, crossing the southern ridge four times, with Crockham Hill, Brasted Chart and Ide Hill on the way.
Route
  • Annual Events

Tour of the Isle of Wight

  • 128.6km
  • 2,094m
A London Dynamo tradition: an early morning ferry from Portsmouth, then anti-clockwise round the island via the Cowes chain ferry, the Needles climb and the breezy Military Road.
Route
  • Kent

Deep Kent Woods

  • 134km
  • 2007m
A long loop deeper into Kent, to the edge of East Sussex, on quiet, rolling, heavily wooded roads south of Tunbridge Wells.
Route
  • Gravel

The Henry VIII Gravel Loop

  • 139.4km
  • 2,077m
Extends the Chartwell loop south to Hever Castle and Chiddingstone, with a steep climb up York’s Hill on the way home.
Route
  • Surrey Hills

The Surrey Octopus

  • 147.7km
  • 2,356m
A gruelling ride that goes up and down Leith Hill eight times from different angles, with little recovery between the climbs.
Route
  • Kent

Ashdown Forest Loop

  • 151.3km
  • 2350m
A long day based on the Hell of the Ashdown sportive, with deep forest riding through Ashdown Forest and Five Hundred Acre Wood, plus legs to and from London.
Route
  • Annual Events

London to Brighton to London

  • 175.5km
  • 2,009m
An annual late spring ride that starts just ahead of the official London to Brighton ride, heading due south through Sussex over Ditchling Beacon and returning through the Surrey Hills.
Route

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