Cycling from London to Windsor

In the spring, when the entire UK was locked down and we could only leave our homes for food, medicine, and one form of exercise a day, I had a brilliant thought: what if I used my one form of exercise a day to go all the way to Windsor Castle? Unlike other countries, we had no limitations on what distance from our homes this exercise could take. And quite frankly, with all the cycling and walking I was already doing, places that had once seemed so far away didn’t look so distant on the map anymore. What else was I going to do with all of those spring bank holidays?

In the end, the days we had off in the spring were all too windy for me to get up the motivation to cycle so far, and I was still wary of the crowds of people who were now spending more time outdoors – but the idea never really escaped my mind. When we were given a company-wide day off in August to avoid burnout, I decided it was finally time to push myself physically instead and make the roundtrip by bike.

The weather report on 21 August was not promising. I didn’t have to worry about rain, thankfully, but the wind was threatening to ruin my day. The circles that depict wind on BBC’s weather report were coloured in black to indicate extremely high winds of more than 40 mph (about 65 km/h). But I knew this was the last summer day I’d have where I could avoid the weekend crowds, so I switched into “learning to live with British weather” mode and packed my bag to go.

I always assumed London to Windsor was a popular cycling route, and yet I struggled to find a good map to follow. I don’t have a GPS or mini-computer for my bike, or any tools for mounting my phone onto my handlebars, so I needed something where I could memorize long sections at a time to avoid constantly stopping to pull my phone out of my bike basket. Primarily I followed the route I found on Cycling UK, supplemented by cycling directions on Google Maps.

Since I had become an expert at navigating my own neighbourhood during lockdown, the ride started off enjoyably. I picked the route I wanted to take through Richmond Park and only briefly consulted the map to get to Bushy Park. From there I stopped outside Hampton Court Palace, at that time still closed to the public, to capture some visitor-free photos.

The route became a bit ugly as I entered an industrial area, my view of the Thames hidden behind big buildings. But that soon turned into quaint little towns with cottage houses lining the streets, making me feel as if I’d entered the countryside less than 30 minutes after leaving London.

Somewhere in Sunbury-on-Thames

I continued along the roads past farmers’ fields, crossing the Thames and seeing the locals shopping on the high street in Chertsey. Finally, I crossed over the M25, the motorway that encircles the capital and is considered to be where Greater London ends.

Up to this point, the route had been surprisingly easy (excepting the major hills I had had to climb by being creative with my journey through Richmond Park). Even the wind, while seemingly still hitting those promised 65 km/h, was as often helpful as it was a hindrance. But as I neared Virginia Water, the roads got narrower and steeper. I found myself in the lowest gear of my three-speed bike, forcing each pedal down with all of my might, climbing a hill to get to a red traffic light, aware of the cars lining up behind me who had no room to pass. Thankfully everyone was patient with me.

I only know of Virginia Water thanks to Bill Bryson’s Notes from a Small Island. While keeping my eyes peeled for the Holloway Sanitorium where he met his future wife, I stumbled upon Roman ruins just on the edge of the lake that gives the town its name. After all the hills I had climbed to get there, I thought I at least deserved a quick photo stop.

The route carried on through tree-shaded roads until I found myself in Ascot. Distracted by the traffic, I didn’t even realise I was cycling along the racecourse that hosts the famous Royal Ascot every year.

Quick protein stop

On the map I could see that I was on the outskirts of a woodland that looked to belong to Windsor Great Park. Soon I was passing Legoland and I could feel that I was nearly there! My legs and body were still pain-free, but I was just antsy to arrive in Windsor, get off my bike, and explore the town.

Unfortunately Harvey, my bicycle, was starting to get tired. His chain had already fallen off once – something I was prepared for from recent trips and had brought a pair of single-use rubber gloves in my bag for, to be able to fix the chain when necessary. But as we were pedalling the last major stretch through Clewer New Town, his chain fell off again. The road was full of traffic and the sidewalk next to me was unnecessarily blocked off by a long metal fence with few breaks. Frustrated, I waited for the traffic to die down and pulled Harvey across the road, sniffling and trying not to cry as I wearily lugged a heavy bike around, then fixed the chain with my bare hands and rubbed the oil off my fingers as best I could with some old Pret napkins from my bag. As surprisingly easy the act of cycling had felt up until that point, give or take a few hills, I could tell that I really was getting tired, and it was about time I got to Windsor.

So Harvey and I carried on. Soon we were winding our way through Windsor’s centre, passing tourist shops and busy pubs. After one final hill, Windsor Castle loomed into view. I had made it.

I locked Harvey to a bike rack down a side street where I hoped he’d be safe and carried on by foot. There was no opportunity for me to go into the castle, having not pre-booked a ticket, but I thought I would at least get a glimpse of Windsor Great Park, and the famous Long Walk that leads to the castle.

I enjoy long walks, but one look down the Long Walk convinced me I couldn’t do it then – not on a day when I’d already cycled more than 50 km according to Strava. This time I just admired it. It will be there waiting for me to enjoy it properly on my next trip to Windsor (via train).

Bit long innit

I spent a bit of time walking around Windsor, taking photos of nice pubs, grabbing something to eat, and popping into Fudge Kitchen, a place I visited in Bath back in February that not only sells incredible fudge but also employs the loveliest people to make it. I let myself be talked into getting a box of four fudges again.

Quaint side streets
Nice pubs
Funny pubs
A view of Windsor’s train station
If you can’t treat yourself to a Pret lobster roll after cycling 50 km, then when can you?
This statue of Victoria stands on the road leading to the castle
View of the castle through the gate on the Long Walk

Soon it was time to leave so I could be home in time for dinner. Unfortunately, as I was heading back to Harvey, disaster struck. (Well, actually, disaster struck sometime earlier, but the problem was I wasn’t sure when or where it actually struck.) At some point when taking something out of my very full bag, I’d lost a pouch of essential things I’d packed just in case I needed them. That pouch contained my bike lights, my phone charging cable, hand and face cream, a comb, and my lip balm – altogether at least £60 worth of small but important items.

I was kicking myself for being careless as I retraced my steps through Windsor. I never found the pouch again – the strong winds wouldn’t have helped even if no one else picked it up – and hopped back on my bike feeling dejected. I struggled to pick up the Cycling UK route on the way back and relied heavily on Google Maps as I went back and forth along Runnymede. Finally, I found myself on a beautiful riverside path. While I don’t generally like cycling narrow paths used by pedestrians, the change of pace was welcome after hours of travelling on roads full of traffic – and thew views certainly relaxed me again.

Runnymede is the site of the signing of the Magna Carta

After a brief tour through Staines-upon-Thames I finished the Windsor loop and rejoined the road I had taken out of London.

Harvey and I take one last pit stop (and yes, my face really was that red – no photo editing necessary)

The final journey through Richmond Park felt much easier than the one to start the day – it was good to be nearly home. By the time I got off my bike outside my building, Strava showed I had cycled 99.6 km that day. I briefly considered doing a loop around my neighbourhood to track the full 100, but after all that cycling it seemed like too much work to do even a little bit more.

During those more than five hours on my bike, I thought a lot about whether or not I would recommend this route. Much of it requires you to share the road with motor vehicles, and some drivers are much worse at passing cyclists than others. If all you want to do is go from London to Windsor as quickly as possible, it’s not the most direct route.

But above all, if you really want to challenge yourself, to see if you can cycle from London to Windsor, I highly recommend this journey. You don’t need to be completely kitted out to attempt this; Harvey is a bike meant for cruising, not a sports bike. For me, being able to sit upright for such a long journey is a blessing, and I really value having a basket to put my backpack in instead of wearing it for hours at a time. It’s entirely achievable if you set your mind to it – the longest trip I’d done before this was about 64 km! When you’ve finished the route, you can brag about it for the rest of your life. And, of course, you have truly earned yourself a beer by the time you get home.


7 thoughts on “Cycling from London to Windsor

  1. Kudos to you! That’s quite the trek to make on a “cruiser” style bike, it’s certainly not a super flat journey around Windsor. If you ever do it again you can cut out a bit of the traffic by scooting through Windsor Great Park. It’s a little more scenic than the busy road past Legoland! 🙂

    Liked by 1 person

  2. What a grand adventure you had with Harvey, with all the elements of a good Tolkien story – a quester, a mission, challenges and trials en route, and a successful conclusion. Congratulations on successfully pushing your limits. You definitely deserved the pint afterward. 😊

    Liked by 1 person

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