The Gypsy’s Tent (or Gipsy’s Tent as it was spelt up until the nineties) was built in the 19th century. Although the pub’s address is on Deansgate it was severed from the rest of the street when Marsden Road bridge was built in 1877.
During the latter half of that century a band of travelling dentists would extract teeth at the rear of the building. As seems to have been common in Victorian dentistry a brass band was often present and would play tunes in order to drown out the patient’s screams.
The pub came into the hands of local brewers William Tong in the early part of the 20th century before being taken over by Walkers of Warrington in 1923. Walkers merged with Tetley’s in 1961 to form Tetley Walker but in August 1981 it was decided to put the Gipsy’s Tent (as it was then) up for sale.
A local firm, Bandmatic, took over the pub in 1983. They operated pool tables in a number of local pubs and had also bought the Rose Hill on Manchester Road, which they named Churchill’s. The Gypsy’s Tent was renamed Winston’s when it reopened in September 1984 and a refurbishment saw the former three-roomed pub turned into an open-plan arrangement.
By 1989 Regal Knight Hotels were the new owners  and the pub was sold again in 1996 with the upstairs room transformed into Romany’s function room.
The Gypsy’s Tent was closed in 2007 and although it was put up for sale it appears not to have been sold. According to Bolton Council’s empty property list the owner is a company named PJM Trading Ltd although a company by that name based in Widnes was dissolved in 2011. Attempt to sell the pub appear to have been unsuccessful.