In 1833 Cornelius Prout, who lived on the south side of the Cooks River, opened a punt here which was "capable of carrying a loaded bullock wagon". He charged a shilling per trip. This was replaced in 1841 by a stone and timber bridge, paid for by a combination of money raised by public subscription, and the remainder supplied by Prout. In return for his contribution, he claimed the right to charge a bridge toll until he was repaid. This became the source of local discontent for many years, and several citizens attempted to challenge his right to this extra income.
The tollhouse, known as the round house because of its octagonal shape, was a two-storey building on the banks of the river adjoining the bridge. It is said that occupants had to be taken from the top windows in boats in times of flood. It was errected by the Canterbury Road Trust for the collection of tolls for use of Canterbury Road between 1859 and 1885 was at Floss Street. The tolls were not collected by te Trust itself, but were put up for auction annually. The toll-keepers then became the responsibility of the successful bidder. In 1885, Canterbury Council assumed responsibility for the section of Canterbury Road within its boundaries.
After several court battles, in 1854 Canterbury Road was opened as a Trust Road, and the Government took over the bridge and closed the tollhouse down.
"Historic Sites of Canterbury", Canterbury and District Historical Society (n.d.)