The idea
What are Bank Holidays for if not for riding bikes?! What’s more, it will be a completely child free one for me (ok, that’s twinged with a bit of sadness too). So positively, I wanted to get out on the bike with a purpose and do something a bit more interesting than just a standard loop to a coffee shop and back.
Along came Chiltern Velo with a social media post that got my creative juices flowing….

Living on the Chilterns we are blessed with a lot of, albeit modest, climbing – Whiteleaf in Princes Risborough features in the original 100 Greatest Cycling Climbs and with some equal modesty is a hill I can claim to have Everested in the recent past.
So, as you’ll see the cool bespoke T Shirt the team at Chiltern Velo have come up with has 9 of the local best climbs on it. Already, I’m thinking “Have I done all of those?”, so checking in with Strava and Wandrer I’m seeing a few hills I’ve not climbed before – The Twist, The Crong (no it’s not some obscure 80’s metal band) and Bison Hill were the obvious ones.
Ok, I’m not the fastest climber, so seeing KOM’s owned by legends such as Rory Townsend and Conor Dunne, now of GCN fame, means I won’t be chasing a maillot à pois rouges.
So how about riding all 9 climbs in order, that’s got to be a decent ride, right? And worthy of a T Shirt? Well, how about a Tour de Chiltern Velo?

The café
Bu first, a little plug for a great local business. Chiltern Velo is a workshop and café in Hawridge, near Chesham in the Chilterns. It’s a great little place for a pitstop, offering a great range coffee, teas and food – the cakes are really good and importantly the slice size is ample!! They’ve got a lovely outdoor space at the back with a great view back over the hills and a massive rack for plenty of bikes. If you are in the area, go check them out.
https://www.chilternvelo.co.uk/


The climbs
So, here’s a little more on those infamous 9 climbs;
Climb | Location | Length | Average Gradient | Strava Segment |
---|---|---|---|---|
The Twist | Wigginton, Hertfordshire | 0.2mi | 12.0% | https://www.strava.com/segments/2434575 |
Whiteleaf | Princes Risborough, Buckinghamshire | 0.89mi | 8.6% | https://www.strava.com/segments/618895 |
Aston Hill | Aylesbury, Buckinghamshire | 0.63mi | 8.4% | https://www.strava.com/segments/709044 |
The Crong | Tring, Hertfordshire | 0.35mi | 9.3% | https://www.strava.com/segments/1091024 |
Kop Hill | Princes Risborough, Buckinghamshire | 0.72mi | 8.8% | https://www.strava.com/segments/869135 |
Ivinghoe Beacon | Leighton Buzzard, Central Bedfordshire | 1.84mi | 3.7% | https://www.strava.com/segments/612619 |
Toms Hill | Tring, Hertfordshire | 0.52mi | 7.4% | https://www.strava.com/segments/674433 |
The Hale | Wendover, Buckinghamshire | 0.43mi | 10.1% | https://www.strava.com/segments/671295 |
Bison Hill | Dunstable, Central Bedfordshire | 0.64mi | 8.2% | https://www.strava.com/segments/617752 |
The challenge
Now it’s all fun and games, but a challenge needs some rules – rules make it repeatable and conquerable. So here’s my rules for the ride
- Looped ride – It’s their list, so we got to start and finish at the Chiltern Velo Café & Workshop (of course)…(just pick a day they are open, not a Bank Holiday like me…)
- Follow the order – The 9 climbs must be taken in the order they appear on the T Shirt,
- No U-Turns – to make this a continuous loop, there will be no u-turns at the top of the climb in order to create a shorter, easier route,
- No repeats – You can only hit each of the 9 climbs once, that means you can only climb the hill once and not descend on it,
- All road – this is a road ride, so there will be no gravel or off-road shortcuts.
I’ve actually seen another guy do the 9 hills in a single 100km-ish ride last weekend which was cool – it’s great to see different peoples versions of the same idea. I love the ‘creative’ bit of coming up with an idea and planning it out, so expect to see more of these fun ride ideas in the future from me. Anyway, taking nothing away from the man who was first, I just wanted to ride it my way and a bit longer.
Anyway, I’m not sure there is a reason behind the order of the hills in the list, but a list is a list and for me, you start at the top…
The ride
So the ‘Tour de Chiltern Velo’ ride will be a total of 193km and nearly 2,500m of climbing

Of course, without the rules this could easily be a 100km route, but honestly I needed to get a 200km plus ride in so the rules help push the distance up. Plus it allowed the opportunity to be a bit creative, for instance I’ve added a really enjoyable section via Ashridge House and estate. Once I’ve done the ride I’ll share my thoughts on the hills and route and potentially post a revised version, should anyone want to give it a go and do it faster / better 😉
Comment below, have you ridden in the Chilterns – what is your favorite (or least favorite) climb?