There’s one at the Isle of Wight mountain bike centre at Cheverton Farm called “Plan Bee”.
It has a sign, and everything.
As well as being a pretty crap trail with hardly any elevation, invariably overgrown, it’s also the name of the shift-planning software at work that tells me when The Man is going to be yanking my chain, so it gets my vote.
There were two trails in my local woods, one was called “The Knee Breaker” because it did. This ran parallel to “Islagi” (It Seemed Like A Good Idea) which was sketchy and full of moss coated rocks. Off the top of my head those are the two best names I’ve seen.
There’s a fire road through the woods next to my parents house which has been named ( by me) Plastic Pig.
This is because, when I was a teenager, one of my older brother’s mates had an old Reliant Robin which he had fitted with five point harnesses and would give impromptu driving lessons to the local kids up and down this track which invariably ended up with the car tipping over and rolling onto it’s side / roof.
This old, blue, wobbly fibreglass vehicle was known as the Plastic Pig.
I grin like a loon every time I ride down that track.
“The Roots of Doom” in the Chilterns so named as they were a fearsome* set of roots with a flinty chalky gully… That for most of the year were handily named “The Roots of Minor Inconvenience…”
*They could be occasionally doom ish, but let’s not kid ourselves
Theres a strava run section near me called “Rob is Jewish”
Bummers and the reverse Strava segment Up the Bummers.
I also quite liked ”Bring out yer dead’ which probably doesn’t count as it is (or rather was) a road Strava segment past the local crematorium…