York landed near Chester about 9 September 1460. (By this time the River Dee had silted up and it was often necessary for large vessels to tie up at places on the Wirral, for example Redbank.)
He is known to have been at Chester on 13 September and then moved via Shrewsbury to Ludlow. He was in no particular haste. For one thing he needed to reassure his many tenants in the area that he was back in business to protect them and avenge their wrongs. (They had certainly had a hard time of it since his hasty departure from Ludlow.) Jasper Tudor, Earl of Pembroke, was a potent threat in North Wales, based in what had been York's own castle at Denbigh, and the Duke was doubtless well aware of this threat to his flank. He started recruiting additions to his retinue as soon as he landed, probably glad of every extra sword.
Some authorities believe that York renounced his allegiance to Henry VI at Chester, and began displaying the undifferenced arms of England, an effective claim to kingship. (The arms of Edmund of Langley, which he had used up to this point, were only superficially different, but that subtle difference had massive implications.) It is known for a fact that by the time he reached Gloucester (2 October) he was issuing retaining indentures without the usual saving reference of loyalty to King Henry.
By 17 September news of York's landing had reached London and on 23 September Duchess Cecily set out to meet her husband. (She had been under the supervision of the Duke and Duchess of Buckingham - the Duchess being her sister, Anne - but the supervision does not seem to have been restrictive.) In addition Warwick (already in the Midlands) rode to meet York at Shrewsbury and stayed with him for four days. It is unlikely that they used this time to discuss the price of fish. Warwick then went directly to London. York went on to Ludlow and spent several more days in the Marches before heading for the capital himself.
It is sometimes suggested that York's claim to the throne was a big shock to Warwick and the rest of the Yorkist Party, and that they all stood back in amazement as York did his imitation of a bull in a china shop. This really cannot be true. I suspect that the political wind was in a different direction to the one they had imagined, and that Warwick was quicker in trimming his sails to it. It is of course also possible that during their discussions at Shrewsbury the two men disagreed as to the way forward, and they parted still in disagreement; but it's beyond belief that Warwick was unaware of York's intention to claim the throne.