Earlier this month, the Bar Harbor Public Works Department scrubbed the sidewalk at the corner of Main and Cottage streets, where some political messaging had been on the sidewalk for a while.
The Facebook chatter over the graffiti was hot and furious prior to the message’s scrubbing. Was it chalk? Was it paint? Was it a mixture? Was it legal?
Annlinn Kruger, a Bar Harbor activist, has been putting messages on sidewalks in Bar Harbor and the neighboring town of Mount Desert since 2022. Most of her messaging has focused on conservative lobbyist Leonard Leo, who lives in Mount Desert and has been in charge of multiple advocacy 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. Another local woman has trespassed on the property multiple times.
Most of the Facebook commenters stressed that it wasn’t Kruger’s message that they were upset about, but that the message seemed too permanent to be temporary. Some said that if the message had been promoting a business or something else, it would have been erased by the town much more quickly.
The town has rules that do and don’t allow certain signs or public messaging. Those ordinances are typically — but not always — covered by the town’s code enforcement office. Some are covered by the police department.
What the town’s code doesn’t have is an explicit ordinance against chalking or chalk painting its sidewalks or roads.
In 2022, a police officer told Kruger she could potentially face a criminal mischief charge over it. David Kerns — a captain at the time but now chief — of Bar Harbor and Mount Desert’s shared police department later 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.”
She tries to provide clear messages which people can further explore for themselves, she explained.
The removal by the town’s public works department has nothing to do with the content of the message, Kerns said Thursday.
The town, he said, has recognized the chalk paint doesn’t seem to be as temporary as it was in the past.
Kruger explained some of the process of marking the letters on the sidewalk and why she believes products like Goof Off, used by the town, don’t work.
“Goof Off is formulated to remove oil from concrete. I worry a bit about the town putting toxic chemicals in the bay. And also they’re damaging the concrete. I think their efforts at the corner of Cottage and Main have made the concrete more porous — so the chalk particles penetrate deeper,” Kruger said. “It is not the first time the town has used toxic solvents to try to remove my chalk. It is not surprising that they are not effective; there is no oil in my chalk paint.”
She said that she’s previously reached out to Kerns about some threats.
“I have a right to share my message in chalk paint on the public sidewalk. Others have the right to share their opinion with me and on social media. There are, of course, safety limits. I have never asked for police protection or police action, but about the law and about police protocols,” she said. “In this context, Chief Kerns recently reached out to me. We will continue our conversation. We have spoken over the years. Chief Kerns has always been diligent in the police mission to protect public safety by enforcing the law. He, and Chief [Jim] Willis before him, have always honored the Constitution, Maine Criminal Code, and local codes while respecting my First Amendment rights. Despite — from what I have observed — pressure by a small number of residents and some town officials to use the police to enforce their personal agendas, rather than the law.”
Her messaging in Northeast Harbor has often been hosed away by Leonard Leo staff members, she said. Similarly, she said sometimes staff near the harbor have hosed it away.
Most of her chalking is in Bar Harbor. The latest message was by the Bar Harbor Chamber of Commerce’s visitor center.
“When I first started my chalk paint messaging, then-Town Manager (Kevin) Sutherland and the united Town Council who supported him, seemed intent on diverting town resources to erase my chalk paint messages. It was rather a game of cat and mouse, with town staff even following me around in a truck, hauling out buckets of water. I understand they also used paint remover and some sweeper machinery,” she said. “That stopped for a couple of years, but evidently the town is at it again. I have never found out who actually makes it a priority and how much it costs the town. Then [former] Town Councilor Gary Friedmann pretty much summed it up as ‘we have not answered her questions, we are not answering her questions, and we will never answer her questions.’”
Currently, Kruger has just one active site because it’s early in the season, she’s busy with volunteering.
“I am testing out a new chalk paint and a new message honoring the nation’s 250th anniversary and those who founded and defended it. I only chalk on public sidewalks. After an early misstep, I make it a point to stay away from sidewalks in front of private homes and businesses. I try to pick sites with a lot of foot traffic. Primarily I get a lot of thumbs up and expressions of gratitude from residents and tourists. Many people are happy to share their stories of activism. It is very heartening. Especially when people come back and say they’ve been inspired to look up more information on their own,” she said.
Kerns said that he’ll meet with Kruger before more messages are written and set up parameters about the ease of the messages’ removal.
Kruger said, “We each have something we can do to try to make things better. MDI has an abundance of remarkable activists with amazing abilities. I am just a gadfly — with some chalk, and the Constitution.”
This story was originally published by The Bar Harbor Story. To receive regular coverage from the Bar Harbor Story, sign up for a free subscription here.


