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Bike rides in South West in May 2026

Find bike rides in South West in May 2026 - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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Ride Cornwall’s stunning coastline and celebrate with a proper pint! Scenic routes along the stunning West Coast of Cornwall plus free St Ives Brewery beer at the finish line!
  • Sun 10 May
  • £30-£37.50
Hayle, Cornwall

St Ives Brewery Sportive

Ride Cornwall’s stunning coastline and celebrate with a proper pint! Scenic routes along the stunning West Coast of Cornwall plus free St Ives Brewery beer at the finish line!

  • Sportive 2
  • Beginner-friendly
  • Event village
  • Coast
  • Age 12 & over
Explore breathtaking Wiltshire countryside your way — four routes from 5 to 79 miles, welcoming every rider, every age, every ability.
  • Sun 31 May
  • £5-£30
Trowbridge, Wiltshire

Tour de Trowbridge

Explore breathtaking Wiltshire countryside your way — four routes from 5 to 79 miles, welcoming every rider, every age, every ability.

  • Short sportive 2
  • Medium sportive
  • Long sportive
  • Families
  • Beginner-friendly
  • Event village
  • Park
  • All ages
  • Thu 7 May
  • £175
Penzance, Cornwall

The Southern Divide

  • Off-road cycling events 3
  • Sat 23 May
  • £42-£50
Cheltenham, Gloucestershire

Cotswolds 100 Sportive

  • Medium sportive
  • Long sportive
  • Sat 23 May
  • £99
Swanage, Dorset

Dorset Gravel Dash 50:50 Bikepacking Event

  • 100 miles gravel riding
  • Sun 24 May
  • £50
Swanage, Dorset

Dorset Gravel Dash

  • Gravel events 2
  • Off-road cycling events

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