Sir Hugh had been somewhat addicted to gambling in his younger days, and had made a few debts of his own before he undertook to deal with his father’s heavy liabilities, and in the early years of his married life he had been very much taken up with the difficult and arduous work of paying off the amounts due to the clamorous creditors.  During this process he had been forced to live very quietly, and had incidentally sifted out his real friends from among his relations and acquaintances.  Thus, it is with pardonable pride that he says:  ’Having mastered my debts, I did not only appear at all public meetings in a very gentlemanly equipage, but lived in as handsome and plentiful fashion at home as any gentleman in all the country, of my rank.  I had between thirty and forty in my ordinary family, a chaplain who said prayers every morning at six, and again before dinner and supper, a porter who merely attended the gates, which were ever shut up before dinner, when the bell rung to prayers, and not opened till one o’clock, except for some strangers who came to dinner, which was ever fit to receive three or four besides my family, without any trouble; and whatever their fare was, they were sure to have a hearty welcome.  Twice a week, a certain number of old people, widows and indigent persons, were served at my gates with bread and good pottage made of beef, which I mention that those which succeed may follow the example.’  Not content with merely benefiting the aged folk of his town, Sir Hugh took great pains to extend the piers, and in 1632 went to London to petition the ‘Council-table’ to allow a general contribution for this purpose throughout the country.  As a result of his efforts, ’all that part of the pier to the west end of the harbour’ was erected, and yet he complains that, though it was the means of preserving a large section of the town from the sea, the townsfolk would not interest themselves in the repairs necessitated by force of the waves.  ’I wish, with all my heart,’ he exclaims, ‘the next generation may have more public spirit.’

Sir Hugh Cholmley also built a market-house for the town, and removed the bridge to its present position.  Owing to rebuilding, neither of these actual works remains with us to-day, but their influence on the progress of Whitby must have been considerable.

On a June morning in the year after Sir Hugh had settled down so handsomely in his refurbished house, two Dutch men-of-war chased into the harbour ‘a small pickroon belonging to the King of Spain.’  The Hollanders had 400 men in one ship and 200 in the other, but the Spaniard had only thirty men and two small guns.  The Holland ships proceeded to anchor outside the harbour, and, lowering their longboats, sent ashore forty men, all armed with pistols.  But the Spaniards had been on the alert, and having warped their vessel to a safer position above the bridge, they placed their two guns on the deck, and every man prepared himself to defend the ship.