Detective Martin Brown Lee, a spokesperson for the New York City Police Department, told CNN that the caravan was traveling down Fifth Avenue in Midtown Manhattan and ultimately encountered a group of counterprotesters upon reaching Times Square.
When the caravan met the group of counterprotesters in Times Square, some of the Trump supporters got out of their cars and came to blows with the other protesters, the law enforcement official said.
CNN has reached out to Jews For Trump for comment.
Twelve people were arrested in connection with the clashes across three precincts, according to the law enforcement official. The range of charges included assault, disorderly conduct, reckless endangerment and obstructing traffic.
CNN has reached out to Giuliani for comment.
The clashes between the opposing groups came just over a week before Election Day.