London to Windsor

In Cycle routes, London by Claire

“This route goes out to the west through two royal parks and finishes in Windsor. With the morning pomp and ceremony of the changing of the guards in Windsor and the sight of school boys dressed in formal tailcoats, the town has a slightly surreal atmosphere—at least on the main street underneath the looming shadow of the great castle.” – Condor Cycles

Windsor’s a beautiful, safe sort of distance outside of London. A short day trip that can easily turn into a long, gentle day on a winding route full of distractions. But it’s not a boring ride. It’s long enough to make it feel like a proper outing and, if you follow a certain route you can wind through some of inner and outer London’s best countryside and see more than your fair share of deer.

As a bit of an explanation as to how we came to follow this route: I have a small obsession with Condor Cycles; a store full of beautiful, expensive bikes that I’m stoutly refusing to enter as may then be at risk of buying anything. (I dream of #1. a beautiful green steel bike from there and #2. having a London flat large enough to house a second bike and people who don’t mind such things).

So as a poor substitute for buying bikes that cost a grand, we looked up the Conor Cycles route maps that they have online; they call it #RouteClub. There are a couple of stunning-sounding rides from there (hello Mendipes) but only a few that depart from their London store. This is a route that leaves from the Gray’s Inn Road area and winds out west. It’s a 62 mile route there and back, which Condor recommend will take four hours if you’re a pro. So, translate this to mean ‘three to five hours heading there whilst getting distracted by the scenery’ and then feel free to take the train home. It’s a nice route that you can adapt based on laziness, so you can always return home following their prescribed route along The Thames if you’re feeling keen.


We hadn’t cycled to Windsor before and, after lounging about lazily catching up in Look Mum No Hands, left it nicely late in the day to bother getting on our bikes and pedalling off, before promptly getting to mend my first puncture at Battersea Park. After setting some new records, fixing my first puncture in under thirty minutes (write home), we were on our way. Again.


This part is optional.


The route’s brilliant. Instead of a direct line to Windsor straight west long The Thames, it’s instead a path that carefully takes you through three royal parks. Whilst the route across the city and through Battersea is just as nice as you’d imagine, the roads through Richmond and Putney aren’t always that sexy in parts, once you hit Richmond Park it’s dazzling. I hadn’t seen Richmond Park before and the second we rolled away from the grey A-roads outside it and into the park, the clouds split open and sun burst out. The park felt like a savannah. We spotted a herd of deer masquerading as trees and excitedly ground to a halt to stare. It was amazing.


Then, as you head through the park the strawy grass changes out for really lush, fresh plants and trees everywhere, and suddenly you’ve emerged what feels a lot more like a village rather than the city on the other side.

Second up is Bushy park, which is a smaller, sweet affair located right next to Hampton Court. There’s a long rolling flat road through the middle (Chestnut Avenue) that wraps around a giant roundabout with a huge pond. It’s all very ridiculously nice and there were some more deer, peering at us from the side.

Then finally, you approach Windsor, rounding the East side of the park. Wind through it, down the tarmac route that takes you past a huge lake and a totem pole. I grew up near Windsor and that totem pole is etched into my memory as a real childhood moment. It was wonderful to have cycled from London to visit it on the way. Inevitably, shortly after this we spotted some more deer. By this point, frankly, we were bored of them. Richmond Park had already won the deer of the day award.

Finally, there’s the castle. If Brighton’s an iconic route where you really feel like you’ve reached a fantastic, ultimate finish line, then Windsor’s not exactly far behind. The winding road up to the castle is a steep challenge and makes coming to a final stop all the more deserved. It feels a lot more like a jaunt than a ride to be too mindful about, as a longer one does. But expect the route to take longer if you have to keep stopping to take pictures, peer at deer, prance about in parks, and general cooing as you go. It’s very easy to get distracted.


Before you go

Getting there

  • There’s a cue sheet with directions you can print off to do this step-by-step route, or just plug in the key location into a Google Maps app as you go and letting it take you there, as we did.
  • Or, Condor have a Garmin route, if that’s your thing.
  • Eat

    They recommend a stop in for hot chocolate at Cafe Stop: The Chocolate Theatre Co.


    We skipped that and dived straight into a 16th century pub with windows that spy out onto the castle called The Horse and Groom. After a day of bicycle meandering, their lasagna is the best (though this could easily be weary cyclist hyperbole).

    ClaireLondon to Windsor