Alfie is definitely on the right track, outfit & the right part of the track! 

Looks like the drop down from Glen Vine towards Crosby Church ?

Aye, it was 2014, just before Crosby, Estelle in one & Michael in t'other.

Looking for the when 😀😀

I'm torn between the 1992 junior and the 1995 lightweight ?

I'll go 1990, guess based on the colour scheme of what I think is Phil McCallen's bike - it doesn't look like the later Silkolene / Honda UK bikes.

i will guess 1991 junior

91 Silkolene colours

Yep it was the 1991 250 race - the latest date push start I could find on Youtube 😂

Hey guys n girls, was going through and sorting the last of my late mum & dad's estate bits n bobs in IoM storage over Xmas 
and found this cracking peerless MCN single page pic rolled up in a tube, i'll be putting up a who / what / where soon
which has a nice connection with the above Hailwood pic.

I found this on a forum I frequent. MY best guess is that its Ian Simpson and Owen McNally (+Joey) at the north west. There is a 94 in the bottom right - which if it's 1994 would seem about right. Would be interested to know the actual answer.



Cheers

Sam

Or maybe Woolsey Coulter and Gary Cowan.....

Def Wolsey Coulter on the Francis Neil bike and Gary Cowen on the East West transport bike. Wolsey had some great success in the Brit championships. Gary was destined for greatness in the 250 world championship on Kenny Roberts /Marlboro until he was paralyzed after his Daytona 200 crash.

Anyone having a punt at the where and when (I've no idea but it must be pre-1994)?

Metropole / NW200. My guess would be 1986. Gary’s accident was in 1990 I think and prior to that, he was in the Doc Shop colours for a couple of years prior. Check out the sunflower / Kirkistown race meeting from 1989;

https://youtu.be/sVVoHKlbN1Q

not my pic - it's on FB Manx Radio

15 minute delay announced...

Cracking the flags in Ramsey.....

(sorry couldn't help myself)

OK here we go right back in time - Rider is one of my best mates who has got me into and out of so much mischief..... a MGP Senior winner some time back .. Location is a gimme, it's at the TT but along with rider can you name the specific machine and who rode it previously - obviously it's not MH's machine...but close(clue)....

Crosby?

No idea about the rest. When I saw the helmet my first thought was Nick Jeffries.