Come the Summer, this is the best place to run in Maidenhead

I love to run hilly trails, I feel that there’s nothing better than an arduous ascent and a quad-jolting descent to improve fitness and free the mind from the weeks oppression and stress. And as I quite dislike running on the flat, I pretty much only run hills.

Living in Maidenhead I’m lucky that there are a few biggish hilly trails that I can run up and around that suit my particular style.

Here are two of my favourite hill running routes around Cookham / Maidenhead.

Winter Hill* “Beast me” reps

It’s 100 feet(ish) tall. Goes up like a rocket and has multiple trails that mean you can always find something to suit both the beginner trail runner and the die hard nut. The shortest run is about 5k (from the car park and after a few reps), but can obviously made to be much longer the more you do. It’s also really easy to follow.

*Huh, it’s not actually Winter Hill. Thanks Google!
The big loop was for the dog to get a drink on such a hot day, which she outrightly refused. Ugh.
  1. Starting at the top of Winter Hill in the car park, face the view and run right
  2. Pick up a thin trail and follow it all the way
    • Take the left at the wooden posts a 100 metres from the car park
    • Straight across the roads separated by a drop
    • Take a left at the gravel t-junction
    • Jump the gate 😉
    • And go straight all the way down to the moor
  3. When you hit the moor, you’ll see a hill screaming into the sky on your right with a well worn trail
    • Run up it
    • It has a hidden top, so save something for the end
  4. Once you’re up, head left on the trail and catch a breath
  5. After 50 paces run the technical descent (slippery in the wet) to the left
  6. Hit the moor-floor-once-more (ha!), turn around and repeat in reverse what you just did
  7. And keep on repeating it up and down over the same hill
For true leg smashing training
Rather than turning around and running back-up up the technical hill, head left at the bottom for 100 meters and look left (up the hill). You’ll see the light trodden trail that I’ve made into the side of the hill. It goes right up. It’s a beast. Run up that, technical route down and repeat. Most I’ve done is 10 repeats. It’s horrible and I love it.
For a running break
At times I need to run-off the hill reps, so at the top of the hill where you take the technical descent, take the right turning just before it. The singletrack is a lovely bumpy feel-good run and when you get to the bottom take a left and after the same distance you just ran you’ll see the technical route on your left or you can take the hill rep option a little further on.
Running with a dog?
After a few reps, head down the technical descent and over the wooden bridge. Take the slight left trail from the bridge and head towards the river. There’s easy access for dogs to the water, just watch for cows and swans.

Winter Hill and Bisham Wood loop

This is essentially a combination of the run above, and another run the other side of the car park at the top of Winter Hill. It’s a varied route with only the end hill to challenge you, but it’s ‘bumpy’ and fun. It’s also well shaded, so ideal for midday runs within sunscreen during the week of Summer.

The Bisham part of the loop starts with running in the opposite direction of the above run (left as you face the view from the car park).

This one is harder to follow. Use a GPS if you have one.

This was a run covering Winter Hill > Bisham Wood > Winter Hill
  1. Run along the trail away from the car park
  2. You’ll run onto someone’s drive, follow the trail to the right of the wall
  3. After a minute or so take the left spur near a wooden post up the hill
  4. Moments later you’ll pop out into an open
  5. Run straight ahead into the trees (don’t follow the trail left)
  6. Look for the lightly trodden markings and spacings on the ground and openings between trees
  7. You’ll end up by a road with a trail immediately across it (you can’t see the trail from the other side)
  8. Cross the road and cut across all trails heading far-left for a couple hundred metres
  9. You’ll come to a road at some point and follow it right (follow it right on the trail if possible)
    • If on the trail, take the left turnings; until
  10. At the very long and straight bridleway (either on the road or on the trail) take a right and head all the way to the top
  11. You’ll come to two wooden gates (take the furthest one from you, not the one on the left)
  12. Follow the trail all around until you come to another wooden gate at the top of a large descent
  13. Take that descent heading right and down
  14. Take the slight up-hill right at the first set of signposts into the trees
  15. You’ll pop out near another set of signposts with 4 routes and a wooden gate to your left, take the first right (not the immediate sharp right leading back-up the hill)
  16. Follow this route for 500 metres and then take the left turning down a very steep ‘chute’
    • This left turn is from an intersecting singletrack from the right
  17. At the bottom of the chute take a right
  18. Take care when you come to the road – look for cars and cyclists (this is also my, and many others, cycling hill rep route)
  19. Cross over and take the right up the trail
  20. This is a long and hard hill run, enjoy
    • There are also about 30 steps at the very top too
  21. Before you step onto the road, take the left and follow the trail
  22. If you have a good memory the wooden post you come to is the same wooden post at the start of the run, either run the route again (about 2.5km) or continue along back to the car park
If you’re after something flatter then the moors make for great fast and flat trail routes. If you run during the warmer months you can get a belting ice cream at the Cookham Moor car park. Sometimes it makes it even worth running the flat for a hill-goer like me.