Hoop rolling, also called trundling a hoop has been a favorite outdoor activity for children for centuries. Hoops were shown in an engraving for Jacob Cats's poem Kinderspel as early as 1628 and were frequently included in illustrations of children's activities and games in the late 18th and 19th centuries. Early hoops were of metal; in the 1800s, handmade wood hoops were all the rage as a favorite plaything. The child's hoop was propelled by stroking a one foot dowel or stick along the top.

antique toys "Rolling", "bowling" and "trundling" a hoop really came into its own in Victorian times. Hoops were raced and used for skipping. The Youth's Best Friend, an early book of instruction, illustrates trundling a hoop with the comment that, "This is indeed a very good sport for little boys, Antique Toys: Rolling Hoop but only in cool weather; some little boys make themselves very hot... by which they often become very ill." Many 19th century portraits and photographs include a hoop along side the posed child. The 20th century hula-hoop is a modern day version of this treasured plaything.

Before attempting any of the hoop games it is well to understand how to trundle or roll a hoop. Hoops were made of two materials—wood or iron. Wooden hoops were trundled by being knocked with a stick; iron hoops were propelled in the same manner but it was better to use a hook. The hook was an iron rod about six or eight inches long, curved at one end, and fitted with a wooden handle. Wooden hoops were toys generally allotted to girls while iron hoops were usually played with by boys.

Hoop trundling was a pastime mostly played by boys under twelve years of age. There was a genuine and healthy excitement to be had from a good hoop race, success in which demanded nimbleness of foot, lightness of touch, and dexterity in management. To trundle a hoop with the aid of a stick required little instruction or practice, but the use of the hook was not so simple.

When using the stick careful guiding touches were required to the right and the left of the hoop from time to time to keep it in a straight course; but with the hook the hoop was guided in any direction without any apparent change of manipulation. The hoop would lie started by a gentle stroke from the straight part of the hook; the hook was then be pressed on to the hoop rather more than half-way down to the ground, the pressure being applied more or less gently, according to the speed required. It was then found that without removing the hook the hoop would be kept trundling at any desired pace, and could by the slightest possible turns or twists of the wrist be guided into any desired direction; the sharpest of corners or the smallest of circles were made without any risk of overturning the hoop, and such feats were performed by means of the hook as could never be attained by the stick. Ingenuity devised many descriptions of hoop games.