‘TrumpStock’ makes its way across Peconic Bay, drawing a crowd of supporters and detractors in Montauk

About 40 boats turned out in the Peconic Bay Friday for a fundraising parade promoted by the president’s eldest son, who also made an appearance at the event.

“TrumpStock” was originally scheduled to run from Orient Point to Montauk, but was extended to accommodate an anticipated large number of boats and Trump supporters who had expressed interest in attending. On the morning of the event, just a few dozen boats slowly lined up in Noyac Bay as they made their way east from the north side of Shelter Island, passing Greenport on the way out to the Orient Point Lighthouse and then south to Navy Beach in Montauk.

Across both the North and South Fork, onlookers — some seeking out a spectacle and others looking to show their support or their displeasure with the president — parked along the bay for a view of the flotilla.

“It’s American pride and I want to feel a part of it,” said Scott Kenney of Shirley, who was visiting Montauk and found a parking spot at Edward Vincent Ecker Sr. County Park so he could catch the line of boats coming in. He even brought a kayak and was considering paddling out to the boats to “get a better view of it.”

He wasn’t alone. Roughly 100 people lined the public beach to the west of the Navy Beach restaurant, where even more people stood outside snapping photographs and looking through binoculars as the boats tied down in Fort Pond Bay.

Some even questioned if President Donald Trump was on board the lead boat, “Team Deplorable,” as Trump impersonator Thomas Mundy mimicked the president’s voice and thanked the first dozen boats to arrive in Montauk.

“Tremendous work,” Mr. Mundy could be seen and heard saying through a PA system on the boat. “You did really great. Good people.”

The boaters then listened to what sounded like a recording of a speech from Mr. Trump. While the president did not attend the rally in the bay, he will be nearby for fundraisers in Bridgehampton and Southampton this weekend.

Photos and videos posted on social media by event organizers Boaters for Trump, showed Donald Trump Jr. and girlfriend Kimberly Guilfoyle on “The Official Trump Boat” in Montauk during the event. The boat, which made its way from Jupiter, Florida, appeared as a second headlining boat.

“The Official Trump Boat” led as the remainder of the boats made their way into the bay, where they tied down and partied as dance music played. Many of the boats were heavily decorated with flags and images of the president. Some participants wore No. 45 Trump jerseys and even masks of the president.

As the boats filled in, so did the observers, and not all were there to celebrate Mr. Trump.

“[Expletive] Trump,” one man shouted as he made his way down the Montauk beach, a sentiment that irked some of the president’s supporters, who sat in beach chairs or the beds of pickup trucks to watch the party roughly 100 yards away, many wearing red Make American Great Again. hats

A handful of the parade boats also circled near the shoreline taunting a group of more than a dozen protestors who arrived carrying signs supporting the Black Lives Matter movement and denouncing Mr. Trump. The protestors shot back with some derogatory chants of their own. East Hampton Police observed both from the beach and a marine patrol boat in the water. An officer said Secret Service was also present.

At times the exchanges on the beach led to debates among the spectators, sometimes touching on campaign issues like COVID-19 and the economy, and even some low-brow exchanges that touched on the sexual preferences of the candidates and the male anatomy.

One woman, a school teacher from Montauk who requested not to have her name printed, said she was disappointed in some of the negative exchanges, but wanted to protest the event because she is upset with the current state of the country. Her husband paddled a kayak out to circle the parade boats, carrying a handwritten Biden 2020 sign that read, “Make America Sane Again.”

Ken Walles of Montauk said he feels the president has been treated unfairly. He recalled meeting Mr. Trump 30 years ago and said he was a “gentleman.”

“It’s nice to see support for our president,” Mr. Walles said of the boat parade. “Regardless of who it is, he’s our president. I happen to respect the president.”

Mr. Walles, who previously owned a nearby hotel, was among the first to arrive Sunday and he brought with him both a Betsy Ross and a pair of Trump 2020 flags.  He said he expected to see more boats participate in the event, but attributed the lower turnout to rain that fell at times during the day.

“I think the weather might have shied people away,” he said. “It probably could have been double the size.”