100 mile / 161 km Sportive

Take on our ultimate challenge and be rewarded by stunning views and some the best cycling roads in the country.

Sections of the 100 mile route will not be signed. We will publish a GPX file of the route in advance.
We will publish a GPX file of the route in advance.


Leaving Wallingford via Crowmarsh, the first climb up Clack’s Lane is a gentle affair but guaranteed to get you nicely warmed up for the challenges to come. The first of these is Swyncombe Hill, with gradients maxing out at 12%.

You’re in the heart of the Chilterns now, and despite being early in the ride, you’ll need a rest after Swyncombe Hill. You’re in luck, as the fast descent from Cookley Green to Pishill is a chance to catch your breath and rest your legs ahead of the next climb up Balham’s Lane. The route then meanders up through North End to Christmas Common, and on to the Feed Station at Cowleaze Woods where you can grab a snack and top up your bottle.

Feeling refreshed, it’s time to head on to the top of Aston Hill. Here is where the 60km route heads for home, with the longer routes turning right towards Stokenchurch and heading out towards Princes Risborough. Watch out for the tricky descent out of Radnage, then brace yourself for a very tough climb up Smalldean Lane where you’ll be grinding up gradients of more than 20%. Thankfully it’s only a short one!

You’re up on top of the Chilterns now, and what goes up must come down. More famous for motorsport rather than cycling, Kop Hill provides a thrilling descent as you leave the Chilterns behind you. Heading north, it’s time to relax a little as the route snakes though picturesque villages and beautiful countryside towards Chearsley. This is where the 100-mile route goes it alone and splits from the 75-mile route. You’ll need to be equipped with a map of the route, or preferably a GPS device with the route already uploaded as there are no signs of marshals to direct you for the next 30-miles/48km. You’ll head out past Waddesdon Manor Estate where you’ll find the road interrupted by the odd punchy climb.

You’re at the furthest point from Wallingford now and making the turn for home, but there are still a few tests to come; not least the Cat 4 Muswell Hill, closely followed by the climb up the north side of Brill Hill to the windmill. Take a breather and refuel at the second Feed Station, before re-joining the riders on the 75-mile route for the remaining 27 miles.

Heading for home now, you’ll pass through Great Milton and past Raymond Blanc’s Le Manoir aux Quait’ Saisons. A brief meander through Great Haseley and Little Haseley, you’ll soon be heading up Shillingford Hill and back into Wallingford for a well-earned rest!


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