About This Event

BigWayRound Winchester Trail Festival MONDAY 3rd MAY 2027 BigWayRound, our Award Winning, Gold-rated Trail Running Event is now live for 2027! After an incredible 2026 event, BigWayRound Winchester returns for 2027! 4 distances, incredible views and with a friendly atmosphere guaranteed, this event will suit you whether you are new to the trails or a seasoned runner. DESCRIPTION Discover the beautiful trails around Winchester and challenge yourself over one of our 4 distances; 14 miles, 19 miles, Marathon and 50K Ultramarathon. Bespoke medal, fully stocked aid stations and fully marked and marshalled course. This popular event will sell fast! Your journey around England’s old capital begins in the heart of Winchester. Running along the Itchen Navigation, your first big challenge awaits as you ascend past St Catherine’s Hill and head east across the beautiful undulating trails to Cheesefoot Head. You then have a succession of ‘Big Way’ paths; the South Downs Way, Allan King Way, St Swithun’s Way and the Itchen Way, leading you through quintessential English countryside as the trail meanders alongside the River Itchen past Avington Hall and beyond! START/FINISH LOCATION Winchester Rugby Club, Nuns Walk, Winchester, SO23 7EF CAR PARKING 50K and Marathon - Free parking is available at Winchester Rugby Club, SO23 7EF 19 mile and 14 mile - Free parking is available at River Park Car Park, SO23 7DD DISTANCES & PRICES 14 Mile - £40 19 Mile - £48 Marathon - £58 50K Ultramarathon - £65 WE ARE UNABLE TO ACCEPT CANICROSS ENTRIES AT THIS EVENT REGISTRATION All runners will collect your race bibs from the registration tent at Winchester Rugby Club. Registration is open from 7am – 7:50am START TIME This year we are going to start all distances together in self-seeded waves according to running pace. As we run through Winchester town centre to get out onto the trails, we need to separate the field. It is a chip-timed event so there is no advantage starting in an earlier wave. The paces are those which you think you will average in the event for the distance which you are entered! If the field is too big for a certain pace then we will split it in 2 so timings are approximate. Briefing for ALL RUNNERS will be at 7:55am by the start. 8am – Sub 8:30 minute milers 8:03am – 8:30 – 9:30 minute milers 8:06am – 9:30 – 10:30 minute milers 8:09am – 10:30 – 11:30 minute milers 8:12am – 11:30 – 12:30 minute milers 8:15am – 12:30+ minute milers MANDATORY KIT All runners will be required to carry at least 500ml of fluid with them. Most will have hydration vests but handheld soft flasks will be permitted. As weather is changeable, especially in winter, runners are advised to also wear (and carry) appropriate clothing for the conditions. We also strongly advise runners to download the GPX file of the route onto a wearable watch or mobile device. Although this is a marked course event, arrows can be tampered with, so a good understanding of the route is advisable. BAG DROP Bag drop tents for each distance will be available on the day, in the start/finish area CUT OFF TIMES 14 mile – 4 hours 19 mile – 5 hours Marathon – 7 hours 50K – 8 hours TREES NOT TEES We work with the Trees Not Tees organization. Runners can opt to have a tree planted instead of receiving a finishers medal. CLICK FOR MORE INFO WHAT YOU GET * A beautiful trail run * Incredible views and scenery * Fully marked course * Well stocked aid stations * Bespoke finishers medal * Friendly enthusiastic volunteers * Energetic and fun atmosphere * On course photographers * Excellent value for money * Satisfaction guaranteed

Staying overnight?

Hotels within walking distance of Winchester Rugby Club.

Frequently asked questions