As a hint of autumn is felt in the air, multicolored streamers flutter in the wind. Pink, blue, and green banners adorn the wrought iron fence. Market tents shoot up, one after another, and visual art of all kinds fills each booth to the brim. Original paintings, fine art photographs, hand-built ceramics, fine crafted jewelry, wooden sculptures, blown glass vessels, and printmakers’ etchings dot the small landscape of City Square Park.
For 28 years, the annual event “Art in the Park” has brought the magic of creativity to the community of Charlestown. What we experience every second Saturday of September at City Square Park got its start in 1998 by the then-new small group of artist friends who called themselves the Artists’ Group of Charlestown (AGC).
“There were only about twelve of us in 1997 when we began,” says Dara Pannebaker, AGC Board President Emerita and founding member. “We were having a jam session, brainstorming about things we could do as a group of artists. A whole bunch of ideas were thrown on the table.”
One of the best ideas, Pannebaker shares, was to bring art into City Square Park, which had been rescued from decay by dedicated community members who fought for its renovation. Thanks to the work of architects and urban planners, a ground-breaking ceremony in 1996 re-opened the park to the community. Complete with a park fountain, public art sculptures, and the preserved foundation stones of a Revolutionary-era tavern, it is a stop on Boston’s Freedom Trail… an idyllic setting for a Charlestown art event. “We felt that art and this park could be very compatible,” Pannebaker remembers. By working with the DCR and the Board of City Square Park, Art in the Park was born.
But this handful of friends hadn’t pulled off an event like this before. In the early days, the event was “a bit chaotic… we invited over 60 artists the first year,” Pannebaker smiles. “Later, we decided it didn’t have to be huge. We felt it was more important to make sure it was both inclusive and high-quality.” Through a jurying process, artists would apply to show their work at the event. It was presented as a curated collection of diverse fine art and fine craft offerings. It remains true to that standard today. This is one of the hallmarks of Art in the Park.
Another standout feature is that the artists themselves must be present at their booth. “Many other art fairs don’t require this,” Pannebaker points out. “We feel that when artists are present, it becomes educational.” Attendees of all ages can ask questions about artists’ work and process, learning more about the inspiration, skills, and lifelong effort it takes to create art. In the smaller setting of City Square Park, relationships between local artists and community members are able to form.
In addition to being a free event open to the public, a fun signature aspect of Art in the Park is the ever-popular raffle table. Artists are invited to donate a small art item that community members can buy one-dollar tickets to win. The table is full of many items to choose from, increasing chances of winning. This is particularly fun for children, Pannebaker notes, and gives an opportunity for just about everyone to engage in the activity. All raffle proceeds benefit the AGC, now a formally established non-profit art organization.
When asked about her vision for the future of Art in the Park, Pannebaker shares, “It’s about artists encouraging the next generation of artists who are just getting started.” She recalls the time she met a young artist working at a retail job in Charlestown. Pannebaker invited her to join the AGC. “She told me she hadn’t painted since she graduated from art school. She needed encouragement to come back to painting.” This artist has now been showing at Art in the Park consistently for years. Pannebaker recounts the story of another AGC member whose hand-built sculptures have become very sophisticated and sought-after by buyers. Pannebaker says when artists keep honing their craft, showing, and selling year after year, this is the result. And similarly, this is how Art in the Park has developed, too. “Year after year, we keep learning new things and improving the event. It just keeps getting better and better,” Pannebaker reflects.
A remarkable fact is that the whole event is run entirely by volunteer members of the Artists’ Group of Charlestown, which has grown considerably in recent years to include artists spanning four generations. Many members including Pannebaker have spearheaded Art in the Park since 1998. This year, AGC Artist Member Lisa Nelson is leading the team of volunteers to plan and execute the event for its 28th anniversary. In this way, the AGC’s mission to “showcase artists’ works and provide high-quality cultural programming for the community” is lived out year after year through its member artists, serving the community of Charlestown. Perhaps this is the key ingredient in the “special sauce” that makes Art in the Park so unique.
To experience the magic of Art in the Park, come to Charlestown’s City Square Park on Saturday September 12 from 10:00 am to 5:30 pm (rain date Sunday September 13). Stop at the fountain first, where you’ll meet the volunteers at the Welcome Table and receive a printed directory and map of the 30+ artists to visit in the park.
For more details, visit artistsgroupofcharlestown.com and follow at @agc.stovefactorygallery. The AGC wishes to thank the 2026 Art in the Park Sponsors: Jeanne Finnerty Interior Design, Hood Park, The Warren Tavern, TCB, DiPierro Construction, Trinity Financial, and Cenotech Solutions.