Best
Any sunny, warm day, when the tailwind is constant?
Worst
Probably a loop similar to below (Toughest 1)
Mid 90s??
But... leaving Holmfirth in nice-ish weather, but with a cloudy looking 'Moss ahead
Once on the summit, it started snowing. Heavily
By the time I'd got down to Woodhead, the road was white over
I decided to cut it short, & turned towards the Flouch
By the time I'd got to the layby (where the butty-van always used to be), the snow was coming down big-style, & the road was covered, my jacket was sodden (one of those 'foam' types)
http://www.geograph.org.uk/photo/4625694
I ended up sheltering in the phone box that was there, back then, debating what to do
After a while shivering, I had to say "Sod It!" & continue, as I didn't know what else was in store - weather wise
By the time I'd slithered down over Salters Brook Bridge, & to the Flouch, it was almost gone
By Penistone, it was glorious sunshine again
I've never had the same variances of weather over there again
Toughest #1
Possibly about 1991 - 1992??
A 'loop' ride with my (brother-in-law since 1997), & Nick (still a good friend who is still capable of winning/placing very highly in a V50 MTB race)
Wakefield - Calder Grove - Denby Dale (start climbing)
'Sovereign Crossroads' - New Mills - Holmfirth - Hinchcliffe Mill - Holmebridge - Holme ('drag' all the way from Holmfirth)
HolmeMoss
Crowden - 'Glossop Road'/Devils Elbow - over the Woodhead Line at Torside Reservoir
Glossop
'Snake Pass' (A57)
LadyBower reservoir
Mortimer Road (aka 'The Strines')
Across the Stocksbridge road, & climb some more
Penistone - Ingbirthworth - Upper Denby
Denby Dale - Clayton West
I'll still admit that after that circuit, the ascent to Midgley roundabout almost finished me off
Then home, via Wakefield
Why was is so hard??
The gearing on my Orbit America was a bit high!!
42 x 21 bottom
Even Nick was struggling a bit on Ewden Bank on his Kona Explosif on slicks
Mark (b-in-l) even held onto Joannes (g/f now wife) car coming up there (wuss)
She gamely followed/leapfrogged to look after her little brother/provide water bottles/etc....
I think she insisted, at the time, now (like most of us), all I get is 'Take a housekey'.....
Glossop Station (b-in-l sitting in car, probably eating?)
The gateway that Boonen shot through on a Tour of Britain a few years ago
All. apparantly, resurfaced since the Tour of Yorkshire used it
Toughest #2
Not really that bad, but stupid all the same
Years ago (mid 90's) on my CX bike (ex team-issue Paul Milnes 653)
It was on sprint-rims, I'd put a pair of road tubs on the spare wheels
A loop through Dewsbury - Liversedge - Brighouse - Halifax
Leaving Halifax, towards Salterhebble, a thunderstorm rolled in (rain was forecast)
Up the 'Autobahn' (the dual-carriageway) to jct 24/M62, at Ainley Top
Rain, in rivers, on the road
Visibility appalling - barely seeing more than 2 -3 cars lengths
Down through Huddersfield, still in the downpour
Up the climb to Grange Moor, past the (now) Mining Museum
Rain eventually petering out somewhere near Horbury Bridge
Tough, due to the intensity of the rain, & spray on the 'autobahn'
Stupid, as no spare tub, & I'd lost my water-bottle (in jacket pocket, as it was a proper CX frame, no bottle mounts, or mudguard eyes)
Thankfully, I'm comparatively grown up now...........................