Photo: Mark Percy · CC BY-SA 2.0
High Wycombe · United Kingdom

Cycling & running events in High Wycombe, 2026

1288events this year

1288 races within 80 km of High Wycombe

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

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A few races to know in High Wycombe

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
High Wycombe

Penn 7 & Fun Run

Penn 7 & Fun Run is an annual running event in the United Kingdom, offering two options: a 7-mile race and a shorter Fun Run. The 7-mile race is for runners seeking a more challenging course, while the Fun Run provides a flatter, simpler option for families, casual participants, and new runners. The 7-mile route presents the primary endurance challenge and may feature varied terrain, making it suitable for those with prior running experience. The Fun Run is less competitive, emphasizing participation. Local charity connections and a community focus enhance the event. The series is organized by Penn & Teller.

Road
Run·Trail
High Wycombe

Marlow Trail Run

The Marlow Trail Run begins at Marlow Rugby Union Football Club in the Thames Valley, offering half marathon, 10K, and 5K distances on off-road trails through the local countryside. This summer trail event features staggered morning starts: the half marathon departs at 9:00, followed by the 10K at 9:15 and the 5K at 9:40. The half marathon and 10K are single-lap courses, while the 5K consists of two laps. The climbs are moderate for trail running, with 53m of elevation gain for the half marathon, 23m for the 10K, and 20m for the 5K. The course is marked with trail flags and A5 arrows, marshals provide guidance and encouragement, and entries include chip timing, complimentary race photos, post-race treats, and a themed medal. An event village offers food and drink following the run.

Trail
Run·Trail
High Wycombe

The One To The Castle Windsor

The One To The Castle Windsor is a half marathon in Royal Berkshire, starting at Marlow Rugby Club at 9:30 am. The race uses river trail paths and links its route with landmarks around the Windsor area, with Windsor Castle as the name everyone notices first. The castle gives the event its strongest piece of local identity: it is a royal residence about 25 miles west of central London, first built in the 11th century and used by monarchs since Henry I. Runners can also use the day for fundraising through GoFundMe, and the listed organizer is George Bottomley.

Trail
About cycling & running in High Wycombe

High Wycombe Training Notes

Running: High Wycombe runners get a proper mix from The Rye, the River Wye path, Hughenden Park, and the lanes out toward Penn Fields, Hazlemere, Totteridge, Downley, and Great Kingshill. Wycombe Rye parkrun gives locals a free 5km hit on The Rye every Saturday at 9am, with hard paths, grass, and those steps near Wendover Way. Handy Cross Runners meet at High Wycombe Judo Centre, Booker, on Monday, Tuesday, and Thursday at 7pm. The route covers 9.3 km and climbs 347 m. Penn Seven, Bradenham Blast, and Chiltern Hills Backyard Ultra 24 work as anchor races.

Cycling: High Wycombe riders live on the edge of the hilly Chiltern Hills, so Z2 base miles can turn into climbing work fast. High Wycombe Cycling Club has been around since 1924 and still feels like the beating heart of cycling in Buckinghamshire, with road racing, time trialling, cyclocross, track cycling, MTB racing, social rides, and touring. Locals also look toward Aylesbury CTC, CTC South Bucks, South Bucks Midweek, Swan Wheelers, Summit Mountain Bike Club, Beaconsfield Cycling Club, and Marlow Riders. The Chiltern Cycleway runs 170 circular miles, and Chiltern Samaritans Cycle 2026 is a 40km event. Gussetts Wood and Ibstone bring the tough climbs.

Season: Summer suits High Wycombe when The Rye is busy early, Pann Mill opens, and July finishes can mean sun and a pint. Locals use the lighter weeks for intervals on familiar 10k roads, longer runs toward Hughenden Park, and steady riding into Marlow, Thame, Oxford, Abingdon, or Beaconsfield. Winter puts The Crown to Crown Christmas Cracker on the running calendar and pushes riders toward cyclocross, MTB racing, and shorter road spins. Wendover Woods, Aston Hill Bike Park, and the Chiltern lanes still keep the off-road crowd happy when the long gran fondo feel drops away.

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Coming soon in High Wycombe

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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