Possible Clues:

• Northern area with king gathering in olden times
• County fellow looking up at king on heavy horse
• Poor hosiery clothes kings in old UK region
• Historic county
• County cricket team
• The Royals' take on type of puddings to go with the roast beef
• Rosy hiker moves around northern county
• Risky hero found out in northern England
• Rent subject to Sky -- or new division in England
• Part of the country where there's more than one riding