The original artwork of Fairlop Fair, created by S.H. Grimm in 1774, is located at the Victoria & Albert Museum.

As Fairlop Fair became more popular, concerns arose from the authorities and clergy about its increasing disorder. In 1793, there was an attempt to shut down the fair led by Sir Bamber Gascoigne, MP, along with members of the Society of Archers. A group of peace officers attempted to stop the erection of stalls, shows, and booths, but they were outnumbered by the crowd and ultimately abandoned their efforts. Horse-riding gentry with servants intercepted the Fairlop boat near Romford. Mr. Wilson, the captain of the boat, stated that they had always conducted themselves in a peaceful and orderly manner and hoped to continue doing so. The crew of the boat gave the gentlemen three cheers, which were acknowledged in return as the gentlemen bowed and rode away.

Sir John Tyrell later recounted the challenges of trying to prevent the boat from reaching the fair, expressing skepticism about gaining support for such efforts in the future. He noted that the Deputation and their assistants were greeted with loud and enthusiastic cheers that startled those present. Sir Henry Dudley, known for his involvement in similar situations, could not contain Mr. Bamber Gascoigne, who fled, and it took Sir Henry some effort to catch up with him and calm his fears.

Upon arriving at the fair amidst a loud crowd, the boat made several circuits around the Oak. An official, for reasons that remain unclear, struck the boat forcefully with his staff, resulting in the staff breaking. The crew chose not to linger and headed directly to the Angel Inn at Ilford. The following year, there were no obstacles, and the fair grew larger.