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’s a climb near me called “TFI” which stands for “That Flipping Incline” or words to that effect.

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 climb near me called “TFI” which stands for “That Flipping Incline” or words to that effect.

We used to have “Big Sandy Climb”, well it began with B anyway.

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.

There was a segment on Strava called ‘richard ramirez’, named due to its length, roughness, and penchant for catching you unaware..

Think it’s been removed nowadays.. Understandably

‘Grandad, Dad and the Dentist‘ always raises a smile – not just coz of the name!!

`Mumsnet Backdoors’ Center Parcs, Longleat

“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”

Skullbuggery

From Collins English Dictionary…
“The Act of having butt sex with a skeleton”

*Drops mic*

roadie strava segment outside of Cambridge (and I think near a wildfowl reserve or sumfink) is “Fear of Black Gannet”

[video]https://youtu.be/CeRoi43azds[/video]

I think West of Whistler has some great names:

Mandatory Suicide
Golden Boner (as above)
and others that I can’t remember! 😆

“Tourettes” in Sierra nevada Spain it a kin tw*t up or down!

Local Glasgow trails have a few good ones

Mangina
Broon streak
Avoid the grumpy old man

I also like the “I scream” run at Rivington, although it’s probably spelt “Ice Cream Run” (because of the van sometimes parked at the bottom).

Purple Monkey Dishwasher – http://www.bikefernie.ca/trail/purple-monkey-dishwasher

might qualify as best and worst.

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…