4 - 5hrs





Chess Walley Walk Rickmansworth to Chesham

The Chess Valley Walk is a 10-mile walk through the Chiltern Hills. For another great walk check out my Ivinghoe beacon post. And if you’re looking for one of the best day hikes from London town, guess what? You’ve found it! 

Starting in Rickmansworth and ending in Chesham, or vice versa, the walk takes four to five hours of strolling through timeless English countryside. All within a short tube or train ride to central London. 

It’s an ideal hike for beginners, families, couples, and anyone looking for an escape rather than a physical challenge. The route takes in manor houses, a Roman farm villa and even watercress beds. Yep, that’s right: you get to see watercress sleeping. Lucky you!

For the most part the route winds along the River Chess: so you’ll feel like a king or queen, and you definitely won’t be board. So, check it out! (Chess, get it?!)

A video I made while doing the Chess Valley Walk

A Chess Valley Walk Itinerary

The Route – What to bring and where to start

As it’s a fairly flat half-day linear walk, there isn’t much planning to do outside of where you are going to start and where are you going to eat that well-deserved pub lunch.

You can start the Chess Valley Walk from either Chesham or Rickmansworth station, both of which sit on the London Underground Metropolitan Line from Baker Street. If hurtling through tunnels scares you, then they can also be reached overground on the Chiltern Railways Overground Line, from London Marylebone.

If 10 miles is too much, then you can opt for a shorter walk by departing at Chalfont & Latimer or Chorleywood tube stations.

For food options, eat in either Rickmansworth or Chesham or, for a midway lunch stop, look to Latimer or Chenies: both are around halfway into the walk and have a good choice of hiker-friendly pubs.

Before you set off, get your hands on this cheeky little Chess Valley Walk Leaflet produced by The Chilterns Area of Outstanding Natural Beauty team. Thanks, guys! I love a good leaflet. Oh, and wear wellies or good boots. It can get muddy out there.

Option 1 (My route)

Rickmansworth > Cheshire- [10miles] 

Option 2 

Chesham > Rickmansworth [10 miles] 

Option 3 

Chorleywood > Chesham [7.8 miles] 

Option 4

Chalfont & Latimer Option [6 miles] 


The route is only 40 mins from the centre of big ol’ London town so you’ve got the entire capital’s accommodation at your disposal. However, if you really want to enjoy those post-walk pints and stumble into a bed, then try one of these.

CheniesThe Bedford Arms Hotel

LatimerDeVere Latimer Estate 

The journey begins

My Chess Valley Walk Experience

Intro – Underground, Overground, Rambling Free

Buzzing after the success of my Clarendon way maiden hiking adventure I was itching to get back out of the city for another hike. At least, I hope that’s why I was itching! Hmm.

This time around I was short on time: I just had a morning to kill so I did a little research and came across the Chess Valley Walk. Not only was it less than an hour from my girlfriend’s house, but it was also on the freaking London Underground Line. I could get there on my Oyster Card! Happy days.

Out the door early like a boss, I was skipping along in my snazzy new barefoot hiker shoes toward the Metropolitan Line before the city had risen properly. I was armed with just a coat, hat and camera. Not even a backpack. Jeez, I’m loving this day-hiking lark already.

Where does the Chess Valley Walk start?

For me, it started in Rickmansworth High Street, at Starbucks. Boo! Yeah, I know I’m typically an independent coffee shop man myself, but it was early and the hipsters that run the best coffee shops don’t get up as early as the big chain boys. 

A big ole cappu later and I was buzzing on a caffeine cloud as I strode out of the town centre, down to meet the River Chess for the first time. My faithful companion for the next four hours. And very pleasing on the eye she was, too.

Follow the fish: Is the Chess Valley Walk well-marked? 

All along its route, I found the Chess Valley Walk to be very well-marked. All you have to do is follow the fish. As soon as I got to Rickmansworth Park – which was looking delightful in the morning light – I picked up the blue and white fish symbol that marked the route and after that, I was in no doubt. 

That said, the route gets a little confuddling around Loudwater Lane as the public footpath leaves the river and you get kettled for a few hundred metres through a rather ugly big fence section. This is soon followed by a very manky section, where you squeeze between some ugly buildings and cross the M25.

I did not expect this, nor enjoy it!

Fortunately, again we’re talking only a few hundred metres of ugliness in a few hours of beauty. I can handle that. After this little section of ugly the real Chess Valley Walk begins in earnest.

The Walk Gets Going: Chorleywood House to Sarratt Bottom

“When I ask for a watercress sandwich, I do not mean a loaf with a field in the middle of it.” Oscar Wilde

The rumble of the M25 faded into a distant memory as I entered the Chorleywood House Estate. Which was lovely. I wandered past lime trees and mighty oaks. I love a good oak, me. And onward toward the Sarratt Mill and Sarratt Green, both parts of the Sarratt Bottom Natural Reserve.

Now, Sarratt Bottom Is a funny name. Anything involving bottom is a funny name, that’s a fact. It’s also a fact that this is a lovely part of the walk, involving narrow paths, wooden walkways, and little bridges. It’s also a fact that Sarrat Bum is home to the Chess River’s last working watercress farm.

Hello wooden walkways and little bridges

Chenies Lunch Stop: If I’d Had the Time

After the excitement of the watercress, I was hungry. The Cock Inn in Sarratt Bottom is, by all accounts, a very hiker-friendly spot. As are the Bedford Arms and Red Lion in the next village along the route, in the village of Chenies. 

But alas, if you are following the fish, the Chess Valley Walk doesn’t take you into either village. Both require a short detour. The same goes if you want to see the famous 15th-century Tudor house, Chenies Manor.

Unfortunately, I’d dallied too long at Starbucks earlier and was playing catch-up for time. So on I pressed, stomach a-grumbling.

It was then, fuelled by my hunger fumes, that I coined my very first hiking aphorism. Maybe the first of many to come. If I ever sell merch maybe this can be one of my sayings.

“A half day to do a half-day hike is good…but a full day is gooder.” 

– Me, Mike, HikerHero CEO

What do you think? Catchy, right?

A full day would mean I could’ve sat on all those lovely benches I’d seen. Skipped a few stones in the water, conversed with a hedgehog and especially, have eaten a mighty pub lunch. But as it was, I needed my hours for walking. 

Frogmore Meadow Nature Reserve: Vole Hunting

Distracting me from my grumbling belly was the beautiful meadow I’d found my way into. Frogmore Meadows, a biological site of “Special Scientific Interest”, or so my leaflet told me. 

Not, in fact, famous for having more frogs than your average meadow, Frogmore Meadows is actually one of the last refuges of water voles, the UK’s fastest declining mammal species. Think wet hamster. This is a great spot to see one of the critters. Apparently.

I kept my eyes peeled…but I saw shit.

That’s not to say there wasn’t a herd of them playing a spot of water voley-ball just over the hill. Just that I didn’t spot them. I also didn’t see any Red Kites. Or any Brown Trout. And I especially didn’t see  “the spectacular banded demoiselle damselfly”. 

Basically, I saw none of the wildlife that the Chiltern tourist literature primed me to be on the lookout for. I did see some cows and a herd of horses. That was it. I’m not complaining, it was a very charming herd of horses. Their horsey flanks glistened in the sunlight.

Shiny horses

Rickmansworth to Chesham or Vice Versa

It was around Frogmore Meadows that I started meeting more hikers, most coming toward me from Chesham. Maybe I was earlier than your average cat, so got ahead of the Rickmansworth crowd. Or maybe the route is more popular in the opposite direction. I’m not sure. 

I did, however, enjoy the snippets of conversation I heard. People talk about some weird shit when they think they are alone in the woods. 

Latimer: A Quintessentially English Village

After Frogmore Meadows came the quaint village of Latimer. It was here that I started thinking about how lucky we are in the UK to have such attractive villages. It was all so quintessentially English: whitewashed cottages, a village green, just idyllic.

Just outside Latimer village, you will come across the aptly named Latimer House, as I did. Once a big ol’ stately house with a fascinating history, during the war, it was turned into a secret M15/M16 base for interviewing captured Nazis, and more recently, a luxury hotel with the swanky title: the DeVere Latimer Estate. 

Man, I bet they do a good watercress sandwich! (The hotel, I mean, not the Nazis.)

The river widens here and the narrow path rises a little, giving pretty impressive views of the rolling countryside. A great place for a picnic, had I prepared one.

Watercress sandwich place

Frith Wood to Chesham: Chess Walk End Game

The stretch after Latimer takes in more rolling Chiltern Hills views before rising away from the river and through the sun-dappled Frith Wood; at least, it was sun-dappled on my morning.  

The path then dips back along to follow the banks of the River Chess, over stepping-stones, and past mini waterfalls complete with rope swings. Again, all so quaint, all so very English. 

Entering Chesham, a lovely old town overflowing with charming brick and flint cottages, I arrived with a satisfied soul but an empty belly. I was famished. That level of hunger where you’re convinced you can hear your stomach chewing on your fat reserves. 

I needed to eat, but then I was caught in that classic dilemma of grabbing something quick and jumping on the tube or getting a sit-down meal in one of Chesham’s lovely establishments – such as the highly praised The Queen’s Head – and waiting for a later train. 

Deciding my day would get complicated if I arrived back too late, I popped into a petrol station and got myself a soft baguette. It definitely wouldn’t have won any culinary awards but it was weighty. Nothing worse than a lightweight bread snack. 

Sitting on a handy bench next to a half-drunk bottle of Corona, I nodded enthusiastically at two dogwalkers wandering past. They gave the beer a bit of a look and me a look and came to the conclusion I was a hobo and not worth a return nod. Rude. Well I never, their loss. 

Midway through reading Laurie Lee’s fantastic As I Walked Out One Midsummer Morning, I’d been quite taken by the hobo lifestyle of interwar England. There was a romanticism to tramping from town to town following the seasons. But anyway, no time to get into that, train to catch!

Mini waterfall heaven

Chesham Station: Stalemated by a Late Train

Arriving at Chesham Station with five full minutes to spare, I was, of course, met with “train cancelled” flashing on the monitor. Nerds! 

It was then that I learned, not only is Chesham the furthest underground station from central London and the most northerly, it’s also the one with the most infrequent service – just two trains an hour. Double Nerds!

Never mind, no point getting angry at British public transport for being unreliable; that’s like being annoyed at the rain for being wet. Which I also told myself when it started raining a moment later. 

Still, it was a great feeling knowing I’d just walked ten miles in pure sunshine for it to start raining after I’d finished. It felt like somehow I was an instinctive weather-predicting genius. (If you’ve read my Clarendon Way adventure you’ll know this is far from the truth.)

Final Thoughts: Chiltern-on or a Chiltern-off?!

My Chess Valley Walk was thoroughly pleasant. Everything about it – apart from the bit over the M25 – was pleasant. Even the train being cancelled meant I got to have a nice sit and finish my Laurie Lee book. 

Overall, I enjoyed it rather than loved it. But that was my fault, not the walk. What I think I was missing was either a walking companion or just more time. The River Chess is so cute and the Chiltern Hills so gentle that it would’ve been nice to loiter a while looking for that elusive water vole.

It is a great walk. It’s so easily accessible that it’s an ideal hike for anyone who needs a break from the city for a few hours of greenery. 

Right, I’m off to call my gran to find out how to make a watercress sandwich. I’m presuming there must be more to it than just watercress, right?

Until next time, happy trails, you hiker heroes.

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