I’m going to answer the question in the title straight away. No, I don’t believe you can ride a trail too many times. On a good trail it will never be exactly the same twice. At the top of the page is a heat map generated by the app. Strava of my riding in Brinscal Woods, a few miles from home, since I started using Strava in 2018. The best trail in the woods and, in my opinion, the best trail I’ve ever ridden is shown below.

I’ve drawn the route in blue but what this picture doesn’t tell you is just how many twists, turns, log hops and drop offs there are in the descent. As you can see I’ve ridden this way dozens of times and today I added 2 more descents to the total. It was basically going to be the same ride I did last time out 3 days ago and the trail conditions were likely to be very similar with only a little rain in the intervening period. On the last occasion I found my self feeling very tired by the time I reached the woods and climbed. I wondered if I’d set off too quickly in my excitement so today I made sure I controlled my speed from the start. The wind seemed initially to be coming from the north so was against me but later in the ride it didn’t seem to matter which way I was heading, the wind was still against me!
Doing the steep climb of 415 feet it was hard again today but the wind was certainly against me. I know that the wind can swirl through the hills but it felt like nature was conspiring against me. After around 50 minutes I was at the high point and began the excellent descent from the moor down to the woods. Along the top of the woods I managed the tricky rock strewn slope without stopping just as I had last time. I reckon I have a 50% chance of achieving this so was pleased to have done it twice in succession. The trick is to keep the pedals turning at all times. A slight halt in rotation and a rock is likely to stop you dead. At the other end of the woods I hopped over a fallen tree trunk to find that a rock had been left just where my front wheel landed. Had this been done deliberately by a trail saboteur? Yes, it had. I knew this after the first few corners when I found some big oak branches, which had been torn from the trees by recent storms, laying across the trail. Last time out I’d ridden round them but then gone back to the top the same way in order to clear the trail. I don’t know why anyone would wish to do this. The woodland is owned by United Utilities for the purpose of collecting rain water for the local reservoirs. It has no official footpaths but is an access area with no restrictions on where you can walk. Since no action has ever been taken to stop mountain bikers, such as no cycling signs, it’s clear that the owners have no objection so why an individual feels he can spoil our riding, I have no idea. I cleared 3 branches and returned to the start for the first of my 2 woodland descents.
The trail was running very well and I climbed back up via a woodland route which is steep and hard going. I was feeling much fresher than last time and this continued to the end of my ride. What I did feel today was that I’m now so familiar with the trail that it doesn’t feel as long as it once did and took me a little over 3 minutes to descend, including slowing for some walkers. A big advantage of riding mid week is that I’m unlikely to see anyone. In fact there are some local trails which are too busy with walkers at the weekend so are best avoided. I completed the ride after my second descent with the fairly level trail past White Coppice to the back of my nearest hill Healey Nab. The climb wasn’t nearly as hard as last time and it was good to get some variety, using the purpose built mountain bike trails, which are different to the natural woodland trails, having a firmer mare hard wearing surface. I feel sure the wind was still against me.
