A lifelike pack of “Wolves” created by English artist Sally Matthews is just one of the art installations that have turned a stroll around historic Chestertown, Maryland, into a search and discover mission.

The walkable downtown—named a “distinctive destination” by the National Trust for Historic Preservation for its 18th- and 19th-century architecture—is also an enclave of galleries, artist studios and the new Kent Cultural Alliance Resident Artist Program.

Founded in 1706 along the Chester River, Chestertown was Maryland’s second busiest port city in the mid-18th century, and is home to Washington College, the nation’s 10th-oldest college. Today, it’s also a thriving arts community.

I learned about the Woicke Sculpture Collection—an eclectic trove of 23 large-scale works gifted to the town by art patrons Peter and Hanna Woicke—during a spring 2023 tour led by Ben Tilghman, an associate professor of art history at Washington College and chair of the Chestertown Public Arts Committee. Though he teaches medieval art, Tilghman describes contemporary art and sculpture as his “first love.” He moved to Chestertown eight years ago. “I was excited when I came across the town’s public art master plan and already trying to brainstorm ways to get involved with bringing its vision to life when I learned about the Woicke Collection,” Tilghman says.

Since then, Tilghman has worked with John Schratwieser, director of the Kent Cultural Alliance, and various artists and community members to thoughtfully plan the placement of each sculpture. “I’m just constantly in awe of the [local] talent, energy and goodwill,” he says. “Chestertown is a lively, vibrant place because there’s a real spirit of working together to make things happen here.”

The tour with Tilghman was arranged, in part, by Hilari and Dave Rinehart, owners of Brampton 1860, a historic inn set on 35 acres on the outskirts of town. The couple chose Chestertown for their next chapter when they bought the property in 2020, relocating from Valley Forge, Pennsylvania. Today they host popular “Dining Under the Stars” dinners with local chefs, holiday wreath-making workshops and other seasonal events.

On the day of the tour, our group meets Tilghman at “Broad Reach,” a massive steel wave sculpture by American artist David Hess that was installed in Wilmer Park in 2016 as the town’s first commissioned work. Back then, the newly formed Chestertown Public Arts Committee was looking for “art of the moment,” Tilghman explains. The structure’s evocation of a rolling sea frames views of tall grasses in the distance alongside the Chester River.

But by 2023, the town was getting ready to anchor numerous local landmarks—from Sumner Hall, an African American museum, to the small Betty Ann Connolly Park, which honors a longtime champion of Chestertown’s trees—with pieces from the Woicke collection.

The acquired works, Tilghman explains, reflect the Woickes’ international travels and love of art. Peter was an executive at the World Bank. Hanna served as curator at the Visual Arts Center of New Jersey after studying art history at Saarland University in Germany. When the couple, who live in St. Michaels, Maryland, decided to donate their entire collection as a complete set, they considered a few Eastern Shore towns. They chose Chestertown for its support of the arts and its careful attention to how the pieces would be presented for public enjoyment.

Leading us toward Chestertown’s historic district, a charming enclave of Georgian-, Queen Anne- and Federal-style architecture, Tilghman says that the Woicke pieces will be intentionally scattered throughout town—not concentrated in a single sculpture garden—so that townspeople can live among them. “There is all sorts of research that public art has great public health benefits,” he says.

We stop by Robert Ortiz Studios on South Cross Street, where custom furniture maker Robert Ortiz creates commissioned pieces after taking clients to a Pennsylvania farm where they can select their preferred wood—often walnut or cherry. Next, we walk down the street and around the corner to the Diane Rappisi Fine Art Studio, whose namesake artist, known for painterly portraits and landscapes rendered in oil, pastels, charcoal and graphite, also exhibits and teaches at the Academy Art Museum in Easton, Maryland. Students travel from afar to attend her classes and workshops, which focus on figurative, still-life and landscape painting.

At nearby Massoni Art, an elegant gallery and fixture in the Chestertown art scene for more than 35 years, we chat with owner Carla Massoni before strolling to an intimate pocket park where a hand-carved wooden sculpture, “Ancient Connection” by Walter Bailey, has taken on a silvery patina.

By the time we pause for a break in Fountain Park near the circa-1899 “Hebe Fountain” (crowned by a classical representation of Hebe, the Greek goddess of youth and beauty), I am smitten. I make a mental note to revisit this captivating town at a future date for more arts immersion.

Making good on that goal, I return to Chestertown in December 2024—at which point some 17 sculptures in the Woicke collection have taken up permanent residence in public spaces. My first stop is the 5-foot-tall “Reading Dog” by Jay Lagemann that greets bibliophiles outside the rear entrance to the town library. Cast in bronze, the whimsical canine figure conjures memories of many a good evening spent reading with my sons.

Next, I make my way to “The Dance,” a striking painted steel work by Shakiru-Ola Erogbogbo depicting a Nigerian woman performing a ritual dance. This welded figure comprised of found objects stands outside Sumner Hall, a circa-1908 structure (restored in 2014) and one of only two African American Grand Army of the Republic buildings still standing in the U.S. Now a museum, the building houses a performance stage, social hall and gallery.

At the time of my visit in December, the final six sculptures in the Woicke collection were scheduled to be permanently installed by May. They include three pieces by American artist Don Rambadt, whose work evokes the beauty of birds, and one by the late Ella Tulin, whose 7-foot-tall “Fully Empowered,” a depiction of a woman reaching for the sky, served as centerpiece for the United Nations’ “Progress of the World’s Women” exhibit in 2000.

Lee Kelly’s steel “Inchworm (for John Coltrane)” was due to be installed, its swirling forms paying homage to the legendary jazz musician’s fluid style. The title references a composition the saxophonist adopted and added to his band’s repertoire. Installed in February, the piece’s home is at the head of the nearby Wayne Gilchrest Trail, aka the Chestertown Rail Trail (an intentional nod to Coltrane’s nickname, “Trane”).

Collage artist and author Marianne Sade, who serves on the Chestertown Public Arts Committee, says she delights in observing public reactions to the works—from children patting the heads of the “Wolves” to lively debates over the perceived meaning or message behind a particular sculpture.

“They have the ability to transform, uplift and engage us in conversations about possibility,” Sade says.

Heading out to revisit the “Wolves” among the trees in Wilmer Park—as Matthews envisioned them—I’m reminded of initial concerns among the locals that the skulking lupine figures might scare young children.

But as I approach the pack, a chubby-cheeked preschooler lets go of his mother’s hand and runs gleefully toward the lead wolf, looking straight into its squinted blue-gray eyes, and gives it a long hug.

If you go



Things to do



Pick up a walking tour map for the Woicke Sculpture Collection at the Kent Cultural Alliance site or the Kent County Public Library-Chestertown. You can also read about the collection and its artists at chestertownpublicarts.com . For architecture aficionados, a Walking Tour of Historic Chestertown Architectural Guide , published on kentcounty.com , is available at area inns.

Carla Massoni of Massoni Art ( massoniart.com ) collaborates with architects, interior design firms and art consultants to curate artworks in settings ranging from corporate offices and New York City lofts to American embassies throughout the world. Spring exhibitions at the gallery include landscape paintings of water and reeds, workboats and watermen by two of its most popular artists.

Diane Rappisi Fine Art Studio ( rappisiart.com ) is a gallery, working art studio and teaching space helmed by Rappisi, a contemporary realist painter whose portraits are rendered in oil, pastels, charcoal and graphite.

Hegland Glass Studio ( heglandglass.com ), founded by Patti and Dave Hegland, is a destination for kiln-formed art glass, including a collection of intricately colored bowls and platters.

Discover rising artists at the Kent Cultural Alliance at the Raimond Cultural Center ( kentculture.org ), which hosts working artists in residence. Current works exploring food themes will be on display from May 2 through the end of June.

Take a class at RiverArts Chestertown ( ctownra.org ), which offers art instruction and workshops to participants of all ages, including a clay studio and “Kidspot” with free art activities on Saturdays from 9 a.m. until noon.

The annual Chestertown Tea Party Festival ( chestertownteaparty.org ) , held May 23-25 this year, is the town’s oldest and largest festival. It celebrates Chestertown’s famed resistance to British rule with a tea toss reenactment, Colonial parade, street performances, strolling musicians, 5K and 10-mile runs and other fun.

The National Music Festival ( nationalmusic.us ), held June 1-14, welcomes international musicians to perform orchestral and chamber works. Rehearsals and many concerts are free.

Where to Eat & Drink



The Retriever Bar ( theretrieverbar.com ) has an apt motto: “Come. Sit. Stay.” The raw bar menu highlights oysters from the Chesapeake Bay and its tributaries. Main plate options include Maine mussels steamed in miso, garlic and ginger, and a buttermilk fried chicken sandwich. Open Monday-Saturday, evenings only.

The Kitchen at the Imperial ( imperialchestertown.com ), helmed by chef and owner Steve Quigg, serves seasonal farm-to-table (or water-to-table) fare, including a Sunday brunch.

Evergrain Bread Co. ( evergrainbreadco.com ) is a carb-lover’s heaven specializing in fresh breads, including rustic sourdough and light, flaky croissants. Grab a loaf to go or linger over pastries and good coffee.

Bad Alfred’s ( badalfreds.com ) is a brewpub and distillery serving wood-fired pizza (including a deep-dish option), local craft beer and a popular crab dip.

Where to Stay



With lush landscaping, meadows and woodsy paths, the historic Brampton 1860 ( bramptoninn.com ) is less than 2 miles from Chestertown’s historic center. Enjoy morning coffee on the wraparound porch or sip a drink by the fire while relaxing in one of the brick patio’s Adirondack rockers. The inn’s seven spacious rooms and suites—plus six private cottages dotting the property—offer a range of perks, from soaking tubs to private porches. Rates start at $279 per night. Gourmet breakfast (puff pancakes and huevos rancheros are two guest favorites), homemade scones, afternoon tea and fresh-baked cookies are all included.

The new owners of White Swan Tavern ( whiteswantavern.com ), located a short walk to the town’s galleries and restaurants, completed a 2023 renovation that blends antique and reproduction furniture with modern amenities such as updated bathrooms with glass-enclosed showers. Each of the six period-style guest rooms and suites has a comfortable bed with luxury linens. Rates begin at $150 and include coffee and tea any time of day, plus a full hot breakfast. Read about another place to stay, Great Oak Manor , on page 222.

Christine Koubek Flynn’s travel and arts stories have also appeared in The Washington Post, Coastal Living and Arlington Magazine .

This appears in the May/June 2025 issue of Bethesda Magazine.

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