Annapolis Loves Carlester

Homegrown Ambassador Honored with Mural, Donations 

The man regarded an Annapolis treasure may not be well enough to walk around town any longer, but fundraising efforts are helping care for him and to make sure he’ll always be known along West Street.  

Carlester Smith—a mainstay on the streets of Annapolis for decades—picked up trash and greeted everyone with an infectious smile.  

I myself can remember first seeing him more than 30 years ago as a little girl. He was picking up litter outside of a business on West Street when we stopped for hot chocolate. My best friend’s mother greeted him and then explained to me that he was considered an ambassador in town and kept West Street beautiful.  

After that, I always looked for him whenever I found myself on West Street, hoping to encounter his smile and enthusiasm. 

Known affectionately as The Walking Man or The West Street Walker, Smith is suffering from health issues and is no longer able to get out and about. The community has rallied around him, raising money for his family and donating needed items.  

“Annapolis loves Carlester,” says Carol Lagundo, an Edgewater native who organized an Amazon wishlist for Smith. “For decades people have seen and admired him. When people learned he was in need of help, they didn’t give it a second thought; they wanted to help.” 

Medical supplies, pajamas, slippers, gift cards and more were quickly purchased and delivered to Smith’s family. “We also added some of Carlester’s favorite snacks to the wish list: Cheetos, Oreos and Ginger Snap cookies,” Lagundo says. “The response has been nothing short of amazing.” 

Now, there’s an effort underway to immortalize Smith with a mural in town. 

“Any true Annapolitan who’s been around for a while would vouch for Carlester being a staple for this city,” says Comacell Brown, the artist who will create the mural. “Since he’s recently been confined to his home due to old age and health conditions, we’ve all just missed seeing him around.” 

The effort started with a Facebook post suggesting a mural be created in Smith’s honor. 

“A group of local supporters including myself bonded together through Annapolis historian Janice Hayes,” Comacell Brown says. “In the Facebook post, the question was asked who should be the artist to paint it. By an overwhelming number of tags and reposts I won the opportunity.”  

A virtual fundraiser and open mic night presented by the Annapolis Community Foundation streamed on Facebook Monday night to raise money for the mural. Brown tells us, “A little over 5K was raised so far. We are at the halfway point to reaching a goal of $10K with donations still coming in.” 

“We had several special guests including Mayor Gavin Buckley, his wife Julie, Kevin Lebling, Parris Lane, Jeff Huntington, Carl Corse and many others,” Brown says. “It was a great turnout and we’re hoping to get the mural started this weekend.” 

The mural will be located at Pinkey’s Liquor Store on West Street and will be about 12 feet high and 27 feet wide. Brown knew just how he wanted to paint Smith. 

“I envisioned a colorful abstract background of Annapolis with Carlester doing what he’s best known for: keeping the city clean, on foot with a smile and a wave,” Brown says. “Carlester is a ray of light that shines bright in the heart of many Annapolitans of all races. It’s only fitting to display that in this project. Bold, bright and beautiful.” 

It’s not just Annapolitans who appreciate Smith’s efforts. Last week Governor Hogan’s office presented Smith with a citation for his contributions to the community and the State of Maryland.  

To make a donation, go to or send a check to P.O. Box 5736 Annapolis, MD, 21403, and made payable to ACF/Carlester mural. To purchase items on the Amazon wish list, go to