Annlinn Kruger’s political messages have drawn police warnings and now a four-page letter from the ACLU arguing that her chalking is protected speech, not criminal mischief.
Sep 02, 2026
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BAR HARBOR—The American Civil Liberties Union of Maine has sent a letter to the Town of Bar Harbor’s town manager and town councilors stressing that one of its residents is allowed to chalk her political views on the town’s sidewalks.
The activity, it states, is an exercise of Annlinn Kruger’s First Amendment rights.
The September 2, four-page letter from ACLU Attorney Anahita D. Sotoohi, also expresses that if the town arrests or prosecutes Kruger “for chalking public sidewalks,” it “will create a claim for retaliatory arrest or prosecution in violation of the First Amendment.”
The letter argues that Kruger’s messaging is not criminal mischief because:
“Even particularly durable chalk does not ‘damage’ a sidewalk. Merriam-Webster defines damage as ‘harm resulting from injury to property.’ The sidewalk is not harmed by even durable chalking—it remains intact and able to serve all of its functions. And Ms. Kruger’s chalking is not particularly durable. It is mixed with water, so washes away with a bucket of water or rain.
“Nor can Ms. Kruger’s chalking be considered ‘tampering.’ Tampering with another person’s property can only constitute criminal mischief if it ‘impairs the use of that property.’ 17-A M.R.S. § 806(1)(A). Ms. Kruger’s chalking does not impede anyone else’s ability to use the sidewalk for other purposes such as walking, standing, protesting, applying paint to mark utility lines, or writing advertisements or directions.”
Kruger, a Bar Harbor activist, has been putting messages on sidewalks in Bar Harbor as well as Mount Desert since 2022.
“I am very grateful to the ACLU for their defense of my rights. I hope their clarification of the First Amendment and the Maine Criminal Code will dispel any misunderstandings of the law regarding my speaking up for our most vulnerable neighbors and our endangered democracy,” Kruger said, Wednesday.
Most of Kruger’s original messaging had focused on conservative activist Leonard Leo, who lives in Mount Desert and has been in charge of multiple campaigns to install conservative Supreme Court justices. He purchased his Northeast Harbor home in 2018 and has been the co-chair of the Federalist Society.
Leo’s home was also where a Bar Harbor man had been arrested while protesting. That arrest resulted in a case against two police officers, which was settled. Protests there have been ongoing.
More recent messaging had focused on statements such as “American Democracy = Equal Rights and Civil Law,” “Due Process = US Law” and “1776 = No Kings.”
Earlier this year, Kruger was warned formally by the Bar Harbor and Mount Desert Police Department that “any material other than standard stick chalk will be considered criminal mischief and enforced accordingly.”
At the time, Bar Harbor and Mount Desert Police Chief David Kerns had said that the town had recognized the chalk paint doesn’t seem to be as temporary as it was in the past.
The ACLU letter argues that Kruger can’t use standard stick chalk because it “injured her hands and was physically laborious to use.”
Also, it says, she can’t afford commercial chalk paint and instead developed her own mixture of water and chalk.
“This mixture dissolves in water, washes away in the rain, and wears away with foot traffic. She has used this mixture consistently since August of 2022,” Sotoohi wrote.
In 2022, a Mount Desert police officer had told Kruger that she could potentially face a criminal mischief charge for her messaging on the street. Later, Kerns—who was then a captain—asked officers to not charge Kruger or others for leaving messages on public property because of their right to freedom of speech.
Kruger said, “I do my chalk messaging to bring attention to issues that I think are of significant concern to us all.”
Town Manager James Smith wrote in an emailed statement, “The town respects the ACLU’s role in protecting constitutional rights, and we agree that political expression is strongly protected. The issue here is not the message being expressed or anyone’s political viewpoint.
”What appears to be missing from the ACLU’s letter is an important factual distinction. The material involved did not simply wash away through rain, foot traffic, or normal municipal cleaning. Routine street sweeping and water applications were ineffective, and additional town labor, cleaning methods, and public resources were required to remove the markings.”
Smith said that temporary sidewalk chalk has been often used in the town.
“Bar Harbor has historically allowed ordinary, temporary sidewalk chalk without treating it as a property maintenance concern, and we will continue to do so,” Smith said.
He continued, “The distinction is straightforward and applies regardless of the message: temporary materials that disappear through normal conditions and routine cleanup are one thing. Materials applied to public property that persist and require additional public resources to remove are another.
”The town will continue to respect constitutionally protected expression while also protecting and maintaining public property.”
We’ve reached out for a statement from the Town of Bar Harbor, but did not receive one by press time. If we receive one, we’ll update this story and make a note to let you know.
UPDATE: This story was updated at 1:10 p.m., September 2, 2026, to include statements from Town Manager James Smith.
LINKS TO LEARN MORE
Bar Harbor Correspondence
281KB ∙ PDF file
In Bar Harbor, Chalked Political Messages Spark Discussion.
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