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Home › Months

Cycling events in May 2027

UK gravel rides, sportives, closed-road events and festivals taking place in May 2027.

22 events · Map

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

    Pan Celtic Gravel Rally

    Sat 1 – Mon 3 May 2027 Llanrwst

    Gravel 136, 94 and 18 km

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

    Tour de Manc

    Sun 2 May 2027 North West

    Road sportive 60, 113, 161 and 200 km

    From £35
  • Two cyclists on a rural path between green fields and hills

    Highland Trail 550 2027

    Sat 8 May 2027 Scotland

    Gravel 885 km

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

    La Roue 2027

    Sat 8 May 2027 Chester

    Road sportive 132.2, 80.8, 46.5 and 42.4 km

    From £27.50
  • A group of road cyclists on a mountain road

    The Lincoln Grand Prix Sportive 2027

    Sat 8 May 2027 Lincoln

    Road sportive 161, 121 and 85 km

    From £45
  • A bunch of riders on a closed street with spectators

    Etape Caledonia 2027

    Sun 9 May 2027 Pitlochry

    Closed-road ride 64, 89 and 137 km

    Price: see organiser
  • 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

    Taunton Flyer 2027

    Sun 9 May 2027 Smeatharpe, Honiton

    Road sportive 163, 100 and 60 km

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

    Wheelbase Fred Whitton Challenge 2027

    Sun 9 May 2027 Grasmere

    Road sportive 180 km

    From £125
  • Two cyclists on a rural path between green fields and hills

    The Gralloch 2027

    Fri 14 – Sun 16 May 2027 Gatehouse of Fleet

    Gravel 53, 111 and 323 km

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

    RIDE Suffolk Sunrise 2027

    Sun 16 May 2027 Framlingham

    Road sportive 68, 105 and 164 km

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

    Tour of the Peak Sportive 2027

    Sun 16 May 2027 Bakewell

    Road sportive 182.1 and 95.6 km

    From £40
  • A group of road cyclists on a mountain road

    Bryan Chapman Memorial 600

    Sat 22 – Sun 23 May 2027 Chepstow

    Road sportive 600 km

    From £70
  • A group of road cyclists riding along a sunny tree-lined road

    Cotswolds 100 Sportive 2027

    Sat 22 May 2027 South West

    Road sportive 166 and 104 km

    From £40
  • Close-up of a rider on a gravel bike on a gravel path

    Tor Divide

    Sat 22 – Sun 23 May 2027 East Midlands

    Gravel

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

    Trough of Bowland Cycle Sportives

    Sat 22 May 2027 Carnforth

    Road sportive 87 and 164 km

    From £50
  • 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

    Startline Leicestershire Sportive 2027

    Sun 23 May 2027 East Midlands

    Road sportive 161, 121 and 90 km

    From £36
  • Close-up of a rider on a gravel bike on a gravel path

    Dorset Gravel Dash 2027

    Sat 29 – Sun 30 May 2027 Worth Matravers

    Gravel 100 and 161 km

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

    Pennine 500 2027

    Sat 29 May 2027 – Wed 2 Jun 2027 Mytholmroyd

    Gravel 508 km

    From £85
  • A cyclist on a winding green countryside road

    Ride4Red

    Sun 30 May 2027 Bristol

    Road sportive 58, 61 and 102 km

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

    White Rose Classic

    Sun 30 May 2027 Yorkshire and The Humber

    Road sportive

    From £38

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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