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The South Downs Way in spring
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Cycling events in South East England

Upcoming gravel rides, sportives, closed-road events and festivals in South East England.

20 events · Filter these · Map

  • Two cyclists on a rural path between green fields and hills

    Highwayman's Trail

    Sat 17 Oct 2026 Princes Risborough

    Gravel

    Price: see organiser
  • A group of road cyclists on a mountain road

    The Kent Classic 2026

    Sat 24 Oct 2026 Lingfield

    Road sportive 112, 82 and 47 km

    From £30
  • An audience listening at a conference talk

    Reframing the Message: Local Campaigning Conference

    Sat 14 Nov 2026 Reading

    Industry event

    Price: see organiser
  • Close-up of a rider on a gravel bike on a gravel path

    Dirty Santa MTB

    Sun 6 Dec 2026 Guildford

    Gravel 45 and 34 km

    Price: see organiser
  • Two cyclists on a rural path between green fields and hills

    Shackleford Turkey Burner MTB

    Sat 9 Jan 2027 Shackleford

    Gravel

    Price: see organiser
  • Two cyclists on a rural path between green fields and hills

    Chilterns Wildwood Gravel 2027

    Sun 31 Jan 2027 Woodcote

    Gravel 40, 60 and 80 km

    Price: see organiser
  • A cyclist on a winding green countryside road

    Hell of the Ashdown 2027

    Sun 28 Feb 2027 Lingfield

    Road sportive 105 km

    Price: see organiser
  • Two riders on a dirt road between fields

    Surrey Hills March Hare

    Sun 28 Feb 2027 Guildford

    Gravel

    Price: see organiser
  • A group of road cyclists riding along a sunny tree-lined road

    Chichester 100 Sportive 2027

    Sat 3 Apr 2027 Chichester

    Road sportive 163, 110 and 47 km

    From £35
  • A group of road cyclists riding along a sunny tree-lined road

    Spring Onion Sportive 2027

    Sun 18 Apr 2027 Cobham

    Road sportive 107 km

    From £39.95
  • A group of road cyclists on a mountain road

    White Horse Challenge 2027

    Sun 18 Apr 2027 Shrivenham

    Road sportive 145 and 113 km

    From £40
  • A cyclist on a winding green countryside road

    The New Forest Classic 2027

    Sat 24 Apr 2027 South East

    Road sportive 127, 92, 53 and 17 km

    From £15
  • A group of road cyclists riding along a sunny tree-lined road

    RIDE Castle 2027

    Sun 9 May 2027 Tonbridge

    Road sportive 58, 117 and 161 km

    From £38
  • A group of road cyclists on a mountain road

    San Fairy Ann CC Sportive

    Sun 23 May 2027 Marden

    Road sportive

    Price: see organiser
  • A cyclist on a winding green countryside road

    New Forest 100 Sportive 2027

    Sat 5 Jun 2027 Fawley

    Road sportive 161, 105 and 57 km

    From £35
  • Smiling cyclists on a group ride

    Joyride Festival Isle of Wight 2027

    Fri 11 – Sun 13 Jun 2027 Isle of Wight

    Festival

    From £1950
  • A cyclist on a winding green countryside road

    Isle of Wight Sportive 2027

    Sun 18 Jul 2027 Freshwater

    Road sportive 122 km

    From £39.95
  • A group of road cyclists on a mountain road

    Isle of Wight Randonnee with Mountbatten 2027

    Sun 5 Sep 2027 Isle of Wight

    Road sportive

    Price: see organiser
  • A cyclist on a winding green countryside road

    The New Forest Tour 2027

    Sat 18 Sep 2027 South East

    Road sportive 162, 119, 75 and 17 km

    From £15
  • A group of road cyclists on a mountain road

    The Surrey Monster 2027

    Sun 19 Sep 2027 Cobham

    Road sportive 200 km

    From £49.95

UK Cycle Calendar

UK cycling events: gravel, sportives, closed-road rides and festivals, checked against organiser pages.

Facts come from organisers' own pages and are checked on the date shown on each listing. Always confirm details with the organiser before you enter or travel.

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