20 Classic Sportive Rides in South East England

Graded routes on cycle-friendly roads between Kent, Oxford and the New Forest

By Colin Dennis

This guidebook offers 20 sportive routes in the most challenging and scenic cycling areas of south east England. From the Surrey and Chiltern Hills to the New Forest and Berkshire Downs, the area boasts miles of cycle-friendly roads suitable for sportive training. The graded routes are all on quiet country roads and can be mixed and matched.



From early winter starts to lazy summer evening rides, all the routes in this guide book are perfect as part of your year-round training regime.


Sevenoaks, Maidstone, Brighton, Reading, Windsor, High Wycombe, Portsmouth, Southampton, Basingstoke, Newbury, Eastbourne, Fleet, Reigate, Dorking, Redhill, Brockenhurst, Marlow, Theale, Hungerford, Oxford.


Sportive cyclists of all levels of fitness and ability will benefit from a mix of flat, cadence training specific rides to unforgiving lung-bursting routes where climbing is the name of the game. Check out the hill grades to each ride and choose the route on which you want to train. Don't forget to mix-and-match your routes for variation of training.
Must See

Must See

20 cycle sportive training rides that cover the most challenging and scenic areas of the Southeast of England: The New Forest, North and South Downs, the High Weald, Surrey Hills, Chiltern Hills and the Berkshire Downs all have mile upon mile of cycle friendly roads on which to train for your favourite cycle sportive event.
5 Mar 2015
17.2 x 11.6 x 0.8cm
  • Overview

    This guidebook offers 20 sportive cycling routes in the best cycling areas of south east England. The training rides range between 60 and 117km (37 to 73 miles) in length, and offer a wide range of challenge, from flat routes for pacing training, to tough, hilly routes to climb.

    The 20 sportive routes are found in Buckinghamshire, Berkshire, Oxfordshire, Wiltshire, Hampshire, Kent, Surrey and East Sussex, a collection from near Oxford down to the south coast by Bournemouth and Portsmouth.

    From the Surrey and Chiltern Hills to the New Forest and South Downs, there are miles of cycle-friendly roads suitable for sportive training. All 20 routes are graded for difficulty and include timings, ascent, food-stops and access information, as well as annotated route maps and clear route descriptions.

    Sportive cycling is a growing sport, and this guide provides routes for experienced riders and those new to this sport. Useful information on bike maintenance and equipment, to travelling around the areas with your bike and advice on accommodation is also included. The result is a sportive guidebook that will prepare you for the challenges ahead, and allow you to explore the best cycling the south-east has to offer.

  • Contents

    About sportives
    The south east of England
    Getting there and getting around
    When to go
    On the road
    Bike maintenance
    The rules of the road
    Feed stations
    Using this guide
    The Routes
    Route 1 Rattle and Hum: Brockenhurst (New Forest)
    Route 2 Pony Express: Brockenhurst (New Forest)
    Route 3 Kings of Meon: Portsdown Hill (Hampshire)
    Route 4 Top and Tail: Queen Elizabeth Country Park (South Downs)
    Route 5 Windoverstoke: Andover (Hampshire)
    Route 6 The Gibbet: Hungerford (Berkshire)
    Route 7 Dragon Slayer: Hungerford (Berkshire and Wiltshire)
    Route 8 Isis: Reading (Berkshire and Oxfordshire)
    Route 9 Devil’s Highway: Theale (Berkshire and Hampshire)
    Route 10 The Hog’s Back: Fleet (Hampshire and Surrey)
    Route 11 Mud, Sweat and Gears: Godalming (Surrey)
    Route 12 Surrey Hills: Headley Heath (Surrey)
    Route 13 Reservoir Cogs: Redhill (Surrey and Sussex)
    Route 14 Park and Ride: Withdean (East Sussex)
    Route 15 Weald-a-Beast: Sevenoaks (Kent)
    Route 16 Battle Plan: Eastbourne (Sussex and Kent)
    Route 17 Merry Wives: Marlow (Buckinghamshire and Berkshire)
    Route 18 The Wycombe Wanderer: Marlow (Buckinghamshire and Oxfordshire)
    Route 19 Oxtail Loop: Kidlington (Oxfordshire)
    Route 20 Ox and Bucks: Kidlington (Oxfordshire and Buckinghamshire)

    Appendix A Route summary table
    Appendix B Bike shops and cycle repair outfits
    Appendix C Useful contacts

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    We are always grateful to readers for information about any discrepancies between a guidebook and the facts on the ground. If you would like to send some information to us then please use our contact form. They will be published here following review by the author(s).

  • Reviews

    This backpack-sized guidebook is ideal for those hunting new cycling routes in the South East of England. We're equipped with location, start/finish positions, distance covered, ascent, how long it will take to complete and a grading. The directions are straightforward and easy to follow, and each route comes with a map. The rides range between 37 to 73 miles in length and vary from flat routes for pacing training, to tough, hilly routes. The author has also provided 'feeding stations' so you know where to stop for lunch along the way.

    Outdoor Enthusiast magazine, October 2015

    Colin Dennis has produced two guides that will be of great interest to any cyclist who likes a challenge in great countryside. With many miles in his legs, he is admirably qualified to guide us on these routes; a cheery attitude shines through in the text and will appeal to those who have thought about taking on bigger challenges but have not yet got round to it, or would rather not but like the idea. The author offers advice to both experienced and newcomer alike.

    Most of the routes are around the forty to sixty five mile mark or thereabouts. This makes it especially useful for anyone preparing for a new season of events or
    looking to build up stamina for a “big one.” Equally they give the opportunity to test out one’s ability before joining the crowds up Box Hill or elsewhere. And, actually, these routes would make interesting day rides at a more leisurely pace; refreshment information is given and one can always double (or treble) the times suggested as suitable for the route.

    Routes on Bodmin Moor, Exmoor, Dartmoor, the Cotswolds, New Forest, the Downs and Weald and Chilterns, amongst other southern hills, cannot be flat. Nor is that desirable from the point of view of the challenge rider. Mr. Dennis has sought out hilly sportives. Take a look at the route profiles. For the cyclists travelling at more of a touring pace, the hills make for good views, and grand airy cycling. Many of these routes would make good touring routes with a challenge, though none would be for the faint-hearted. Of course, there’s no need to rush, but, should you wish to do so, then the advice and guidance is here.

    Route directions are brief and to the point and there is little in the way of notes on what there is to see along the
    way. That is not the point of the book. Additional weight is unwanted, and one suspects that the speedster will
    download the digital routes available. In that sense it will be a planning book, though it fits easily in a jersey
    pocket and there is sufficient detail to help with refreshments and accommodation.

    So, a book of do-it-yourself sportives or challenge tours, great for preparation, great for a good day out great for
    encouraging cyclists who want to step up to the big, big challenges. I really enjoyed reading these routes and
    following them in my memory and on the map. A really interesting addition to the library.

    Seven Day Cyclist, September 2016

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Colin Dennis

Colin Dennis has been riding bikes of one sort or another for longer than he dares to remember. His passion for road and off-road cycling has taken him all over the UK and continental Europe, both leading expeditions and for personal pleasure. Plotting, planning and escaping to new locations are pastimes that have driven him for many years, and working as both freelance copywriter and cycle guide provides a happy balance at home and work. Colin is never happier than when he's struggling up a steep climb behind a group, usually covered in mud, but as long as there's a warm tea shop involved – everything's possible.

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