The second fair held at Newburgh, October 8 and 9, 1856, was a great success. The society's tent was erected on grounds attached to Washington's Headquarters, north of which were posts with ties for cattle and pens for other animals, the adjacent lot on the south was used for loose cattle. Arrangements were made with the trustees of the village, and with the owners of property on South William, Liberty and other streets, for the exclusive use of portions of these streets for the exhibition of horses. The plowing match and a trial of plows took place a short distance south of Headquarters. Special attractions were for the first time provided—there was a parade of the entire fire department of the village and a boat race under the auspices of the Newburgh Regatta Association.
In 1858 the second fair at Montgomery was said to have been one of the best then held in the county. One hundred and ninety-seven premiums were awarded.
In 1860 the fair was again held at Middletown. The published accounts represent it to have been still more successful than it had been eight years before.
During these first twenty years of the society's existence it was customary for the executive committee to meet at an early day, fix a date for the fair, prepare a premium list, select judges, and have all published gratuitously in the newspapers of the county. These early fairs were generally satisfactory. The grounds not being enclosed, no admission fee was charged. Articles were exhibited in public halls until 1850, and after that in a tent. The expenses were light, the premiums few and payment was obtained from membership fees and the State appropriation, supplemented by private contributions procured by personal importunity.
At the annual meeting in 1861 the executive committee was empowered to raise by stock subscription a sum of money sufficient to purchase or lease suitable grounds, and to erect buildings and fences thereon—the grounds to be in the vicinity of Goshen. The committee leased the grounds known as the Goshen Driving Park and issued certificates of stock, in shares of $25 each, bearing interest at the rate of ten per cent, per annum. The number of shares was fixed at 100, and no person was permitted to subscribe for more than one share. All the stock was promptly taken, and the building (Agricultural Hall) occupied by the society from 1862 to 1874. During this period the interests of the turf were predominant and not entirely regarded as creditable exhibitions of the products of the farm, the workshop, or the home.
In 1866 the society was reorganized and incorporated. Having failed to secure a renewal of the lease for the grounds, it was determined that the fair building should be sold at auction, and on the 20th of December it was sold for $300. The proceeds of the sale were in part applied to the payment of debts, the balance was divided pro rata among the stockholders, who, as an element of the society, then ceased to exist.
In 1874 the society was therefore composed only of members. It was without grounds. It was out of funds and out of debt—having neither assets nor liabilities. Its exhibitions held many years at Goshen, the residents of that village had tired of them, and the people in other sections of the county took but little interest in them. Several of its leading managers were so absorbed in horse trotting that other departments had been neglected. The number of entries had been reduced to less than 400. The attendance of visitors was comparatively small, and the membership had dwindled to about seventy.
Under these discouraging circumstances, such of the officers as continued to take an interest in the society accepted the invitation of citizens of Montgomery to hold the thirty-fourth fair in that village. The result fully vindicated the wisdom of their action. More than 1,000 entries were made. Many new members were enrolled, prominent among whom was the Rev. L. L. Comfort, whose influence and example did much to elevate it from the condition into which it had fallen. The fairs continued to be held at Montgomery for four years, during which time the treasury was replenished and a surplus fund formed which in 1887 amounted to about $8,000.
The memorable fair in 1878, held at Washingtonville, was the beginning of a new era. For the first time in twenty years no trotting or racing was seen on the grounds. It was in all respects a legitimate and successful exhibition, and was only excelled by that of the following year, held at the same place, when nearly 2,600 entries were made, and 800 premiums, amounting to more than $1,500, awarded. During these two years the Orange County fair was raised to the high plane that it has since occupied.
At Warwick in 1880 and 1881 the excellence of its exhibitions were fully maintained. The additions then made to the society's membership rolls, and to its council board, were of great value, and were largely instrumental in securing the successes of subsequent years.