Donald Trump swooped into the Financial District Wednesday for a high-dollar fund-raiser, drawing some of the biggest names in state Republican politics as the party’s establishment continues to navigate its awkward embrace with the presumptive presidential nominee.

The fund-raiser was part of a broader New England jaunt that took Trump to a rally in Bangor and includes a Thursday press conference in Manchester, N.H.

The region, collectively, has proved resistant to Republicans in recent presidential elections, but Trump has stunned political handicappers at nearly every turn since launching his bid just over a year ago.

Addressing a noontime gathering in the Langham Hotel restaurant, Trump dangled the prospect of making Massachusetts — a state that last voted for a GOP presidential candidate in 1984 — competitive in November.

“He said that they would play in Massachusetts. ‘Unless Scott tells me it’s not worth it, then we won’t,’?’’ two attendees quoted Trump as saying, referring to former senator Scott Brown, who introduced the presumptive nominee.

Trump won over 49 percent of the vote in the five-way Massachusetts primary in March, but the state’s GOP establishment has been cool toward him. Governor Charlie Baker has said he will not vote for Trump in November and will not attend the party convention. Longtime state Republicans concede it’s unlikely that Trump will win the state in November.

But at least some of the state’s bold-faced Republican names turned out Wednesday. New Balance chairman Jim Davis, a major GOP donor, attended, along with state party chairwoman Kirsten Hughes, Boston Herald columnist Howie Carr, automotive heir Ernie Boch Jr., and Patricia Saint Aubin, the party’s 2014 nominee for state auditor. Woody Johnson, owner of the New York Jets and a former Jeb Bush backer, was also on hand.

At the fund-raiser, for which tickets started at $2,700 per person, Trump also hit the trade theme hard, according to fund-raiser attendees.

“A lot of the discussion was about trade, China, Japan,’’ said Janet Fogarty, a state GOP committee member.

Over filet mignon, potato salad, and asparagus, Trump pitched his twin messages of economic and national security, said Fogarty and Louis Murray, another activist who also attended.

In remarks that lasted between 20 and 30 minutes, Trump contrasted his own freewheeling style with presumptive Democratic nominee Hillary Clinton’s more buttoned-down approach.

“He’ll talk to everyone, and he’s going to continue to crisscross the country and do his speeches in stadiums,’’ Fogarty said, describing what Trump told the crowd of about 100.

Murray said Trump also spoke about the insularity of the press, saying it had misread the results of a congressional probe into how Clinton, then US secretary of state, handled the 2012 terrorist attacks on an American diplomatic compound in Benghazi.

The event also drew about 100 protesters across Franklin Street, kept at bay by barriers and a heavy police presence.

Some of the demonstrators chanted, “Hey, hey, let’s be clear, no racists are welcome here’’ and sang, “This Land is Your Land.’’ A range of activists — state Sierra Club chapter members, social workers, self-described communists, Black Lives Matter supporters, and LGBT advocates — stood together, directing their signs and chants at the hotel.

“We think it’s important to stand up against bigotry, against racism, for climate justice,’’ said Emily Norton, a Newton city councilor and Sierra Club chapter director. “He’s a hypocrite and a liar.’’

US Representative Michael E. Capuano, a Somerville Democrat, and Boston City Councilor Ayanna Pressley spoke at the start of the rally.

The protest piqued the lunchtime interest of those who work in the Financial District, with people in suits snapping photos of the rally on their smartphones, or sipping their coffee underneath the shade of the surrounding buildings around Post Office Square.

Later in the day, in Maine, Trump lavished praise on the state and its Republican governor, Paul LePage, before launching into his speech.

Over his hourlong remarks, Trump spoke at length and critically about overseas trade pacts and fired back at the US Chamber of Commerce, a traditional ally of Republicans that has ripped him for his opposition to free trade. The group, Trump said, is “totally controlled by the special-interest groups.’’

Trump’s Bangor speech was attended, as many of his rallies are, by protesters.

Trump applauded Maine, calling it “a big chunk of land, honestly, among the most beautiful states.’’

He said he has not needed to rely on conventional campaign methods to gain popularity. Before the primary in New Hampshire, Trump said advisers told him to knock on doors and “get into people’s living rooms.’’ But Trump said he did none of that and chose to hold rallies — and still won the primary.

Trump added that he also does not rely on television ads to be successful. Clinton, he said, has aired spots attacking him, adding that a recent poll shows the two rivals statistically tied.

“In the old days, they would say, ‘He’s a genius,’?’’ Trump said.

Jim O’Sullivan can be reached at jim.osullivan@globe.com. Follow him on Twitter at @JOSreports. Globe correspondents Miguel Otárola and Meg Bernhard contributed to this report.