A wild guess is Skegness to Grantham - though I can't make much of clues 2 and 3
Correct indeed. Not as difficult as i first considered...
1:
Skegness - One of the most recognised landmarks in the town (The Clock Tower) was erected to mark Queen Victoria's Diamond Jubilee.
2:
Sleaford - All the main points of the compass are served by signal boxes; East and West are passed during the journey.
The town name derives from the Old English meaning "Ford over a muddy stream" (Esla-forde)
3:
Honington Junction - This closed station is also the winter quarters of a Circus; hence the elephants.
4:
Grantham - The town was once a centre for manufacturing, though most has now closed; it is credited with producing the first running diesel engine, in 1892.
A local speciallity - Grantham Gingerbread biscuits - were offered as part of BR's Intercity Afternoon Tea menu.