Councillors will be asked to approve plans for stalls to be put up in the square, which is surrounded by historic buildings including York’s Mansion House, St Helen’s Church, the former Terry’s shop and cafe and Bettys tea rooms.
Under the plans, the Christmas market would come to the square for six weeks, starting after November 12 and finishing before Christmas Day.
But St Helen’s Square is a popular location for protests and police say another suitable site for demonstrations must be found before the market can go ahead.
Council bosses say the stalls must not interfere with the charity Christmas tree that is installed in St Helen’s Square each year, or the carol events held in front of the Mansion House.
They say there should be no more than four stalls and only one is allowed to sell alcohol.
The market must not get in the way of pavement cafes in the area – tables and chairs are in place outside The Ivy, Harkers and The Impossible Wonderbar.
A report adds that counter terrorism measures also need to be discussed.
Councillors rejected plans for street trading in St Helen’s Square in 2016, when they said it was not appropriate because of its “special characteristics”, according to a report.
St Helen’s Church raised concerns about the impact of the stalls on the St Leonard’s Hospice charity Christmas tree, which is installed in the square every year, as well as the effect on delivery vans that drive through the square each morning to reach city centre businesses.
Tourism body Make It York runs the Christmas market, which is mainly based in Parliament Street and St Sampson’s Square.
The report says the area gets “very congested” and has grown in popularity in recent years. As a result, the organisation is looking to space out stalls so that areas do not get overcrowded.
The cost of renting a stall at the Christmas market ranges from £1,120 for a week to £2,695. It is one of the events that brings in the most money for Make It York.
This year’s Christmas market is due to take place from November 18 to December 23.
The 2020 event was cancelled as a result of the pandemic. A meeting to discuss the plan to expand the market takes place on June 8.