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Sportives in South East

Find sportives in South East in 2026/2027 - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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Select an event for photos, video, route, location, reviews, entry fees and how to enter.

King of the castle, or dirty rascal? Expect some tough climbs after departing the imposing Tonbridge Castle with 800 other riders and experience some amazing views across the Kent countryside.
  • Sun 10 May
  • £43.50-£58.50
  • 10% off
Tonbridge, Kent, UK

RIDE Castle

King of the castle, or dirty rascal? Expect some tough climbs after departing the imposing Tonbridge Castle with 800 other riders and experience some amazing views across the Kent countryside.

  • Short sportive
  • Medium sportive
  • Long sportive
  • Beginner-friendly
  • Plastic bottle free
  • Rural
  • Public transport links
  • Age 16 & over
A fantastic social and relaxed cycle through Oxfordshire countryside from one of the best breweries in the Cotswolds, taking you along the most scenic routes - to finish with a refreshing beer.
  • Sun 31 May
  • £30-£37.50
Banbury, Oxfordshire, UK

Hook Norton Brewery Sportive

A fantastic social and relaxed cycle through Oxfordshire countryside from one of the best breweries in the Cotswolds, taking you along the most scenic routes - to finish with a refreshing beer.

  • Sportive 2
  • Beginner-friendly
  • Event village
  • Age 12 & over
Ride out from historic Oxford into beautiful countryside, tackle rolling routes and classic climbs, and finish feeling stronger after a supportive, scenic day on the bike.
  • Sun 21 Jun
  • £20-£45
Oxford, Oxfordshire, UK

Bike Oxford

Ride out from historic Oxford into beautiful countryside, tackle rolling routes and classic climbs, and finish feeling stronger after a supportive, scenic day on the bike.

  • Short sportive
  • Medium sportive
  • Long sportive
  • Families
  • Beginner-friendly
  • Event village
  • Age 12 & over
An early season ride in the heart of Berkshire featuring some of the very best of the North Wessex Downs AONB with three road routes offering something to suit all abilities.
  • Sun 5 Jul
  • £37.50-£58.50
  • 10% off
Newbury, Berkshire, UK

RIDE Wessex Downs

An early season ride in the heart of Berkshire featuring some of the very best of the North Wessex Downs AONB with three road routes offering something to suit all abilities.

  • Short sportive
  • Medium sportive
  • Long sportive
  • Beginner-friendly
  • Plastic bottle free
  • Park
  • Rural
  • Public transport links
  • Age 16 & over
A fantastic cycle through Buckinghamshire from one of the best breweries in the county, along the most scenic routes, to finish with a complimentary beer from the taproom.
  • Sat 18 Jul
  • £30-£37.50
Aylesbury, Buckinghamshire, UK

Vale Brewery Sportive

A fantastic cycle through Buckinghamshire from one of the best breweries in the county, along the most scenic routes, to finish with a complimentary beer from the taproom.

  • Sportive 2
  • Beginner-friendly
  • Event village
  • Rural
  • Age 18 & over
Cycle out from historic Canterbury into the Kent countryside, enjoy rolling lanes and coastal views, and finish proud after a friendly, fully supported day in the saddle.
  • Sun 19 Jul
  • £20-£45
Canterbury, Kent, UK

The Canterbury Bike Ride

Cycle out from historic Canterbury into the Kent countryside, enjoy rolling lanes and coastal views, and finish proud after a friendly, fully supported day in the saddle.

  • Short sportive
  • Medium sportive
  • Long sportive
  • Families
  • Beginner-friendly
  • Event village
  • Age 12 & over
Take a social and adventurous ride from a majestic location hidden away on a tiny rural lane in the heart of the valley, with a freshly pulled pint as your reward. Cyclists' bliss.
  • Sun 26 Jul
  • £30-£37.50
Henley-on-Thames, Buckinghamshire, UK

Chiltern Valley Winery & Brewery Sportive

Take a social and adventurous ride from a majestic location hidden away on a tiny rural lane in the heart of the valley, with a freshly pulled pint as your reward. Cyclists' bliss.

  • Sportive 2
  • Beginner-friendly
  • Event village
  • Age 18 & over
Cycle through the Berkshire countryside from one of the best breweries in the UK, taking you along the most scenic routes to finish with a refreshing, complimentary beer.
  • Sun 9 Aug
  • £30-£37.50
Thatcham, Berkshire, UK

Renegade Brewery Sportive

Cycle through the Berkshire countryside from one of the best breweries in the UK, taking you along the most scenic routes to finish with a refreshing, complimentary beer.

  • Sportive 2
  • Beginner-friendly
  • Event village
  • Rural
  • Age 18 & over
  • Sun 12 Apr
  • FREE-£50
Southampton, Hampshire, UK

The New Forest Classic - Sunday

  • Sportive
  • Short sportive
  • Medium sportive
  • Long sportive
  • Sat 6 Jun
  • £40-£50
Southampton, Hampshire, UK

New Forest 100 Sportive

  • Short sportive
  • Medium sportive
  • Long sportive
  • Sat 27 Jun
  • £30-£40
High Wycombe, Buckinghamshire, UK

Samaritans Cycle Sportive

  • Sportive 3
  • Sun 28 Jun
  • £5-£40
Banbury, Oxfordshire, UK

Broughton Castle Sportive

  • Sportive 5
  • Sat 4 Jul
  • £20
Portsmouth, Hampshire, UK

Round the Harbours Bike Ride

  • Charity bike ride 2
  • Sun 12 Jul
  • £17-£40
Reigate, Surrey, UK

Ride Reigate

  • Short sportive
  • Medium sportive
  • Long sportive

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