A lifelike pack of “Wolves” created by English sculptor Sally Matthews is just one of the many art installations that have turned a stroll around historic Chestertown, Maryland, into a captivating game of search and discovery.
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 first learned about the Woicke Sculpture Collection—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 and was excited to learn that it had a public art masterplan in the works. Back then, the newly formed arts committee was looking for “art of the moment,” he says.
Since then, Tilghman (a descendant of the Eastern shore family for whom Tilghman Island is named) 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 in the Woicke collection.
“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 2023 tour with Tilghman was arranged, in part, by Hilari and Dave Rinehart, owners of Brampton 1860, a historic inn on the outskirts of town. Our group met up at “Broad Reach,” a massive steel wave sculpture by American artist David Hess, installed in Wilmer Park in 2016 as the town’s first commissioned work. The structure’s evocation of a rolling sea frames views of tall grasses in the distance alongside the Chester River. (Fun fact: Hess and his son Eli are also the creators of “Fire Lines,” a bronze and steel sculpture affixed to the facade of Arlington County’s Fire Station 10 on Wilson Boulevard.)
At that point, only a handful of contemporary pieces in the Woicke collection had been installed. Others were soon to find permanent homes in various public locations around Chestertown—from Sumner Hall, an African American museum, to the small Betty Ann Connolly Park, which honors a longtime champion of Chestertown’s trees.
The acquired works, Tilghman explained, were a reflection of Peter and Hanna Woicke’s 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 the University in Saarbrücken in Germany. When the couple, who live in St. Michael’s, Maryland, decided to donate the entire collection as a set, 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 the historic district, a charming enclave of Georgian, Queen Anne and Federal style architecture, Tilghman noted how the Woike pieces were intentionally scattered throughout town—not concentrated in a single sculpture garden—so that the townspeople could live among them. “There is all sorts of research that public art has great public health benefits,” he said.
We stopped 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 walked around the corner to the Diane Rappisi Fine Art Studio, whose namesake artist, known for her painterly portraits and landscapes, also exhibits and teaches at the Academy Art Museum in Easton. Students travel from afar to attend her classes and workshops focusing on figurative, still-life and landscape painting.
At Massoni Art, an elegant gallery and fixture in the Chestertown art scene for more than 35 years, we chatted with owner Carla Massoni before strolling to an intimate pocket park, where a hand-carved wooden sculpture, “Ancient Connection” by Walter Bailey, had taken on a silvery patina.
By the time we paused 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, and cupbearer to the gods), I was smitten. I made a mental note to revisit this mesmerizing town at a future date for more arts immersion.
Making good on that goal, I returned to Chestertown in December 2024. By then, some 17 sculptures in the Woicke collection had taken up permanent residence in public spaces.
My first stop was 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 conjured memories of many a good evening spent reading with my sons before tucking them into bed.
Next, I made my way to “The Dance,” a striking steel work by Shakiru-Ola Erogbogbo depicting a Nigerian woman performing a ritual dance. Composed of found objects welded together, the figure 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.
This year, Lee Kelly’s “Inchworm (for John Coltrane)” was installed at the head of the Wayne Gilchrest Trail, aka the Chestertown Rail Trail, in an intentional nod to Coltrane’s nickname, “Trane.” The title of the work references a composition the legendary musician adopted and added to his repertoire. The sculpture’s swirling steel forms pay homage to Coltrane’s fluid style.
The final remaining works in the Woicke collection are scheduled to be permanently installed in May. They include three bird-inspired forms by American artist Don Rambadt, and a 7-foot-tall feminist depiction of a woman reaching for the sky by the late Ella Tulin. The latter figure, titled “Fully Empowered,” served as a centerpiece for the United Nations’ “Progress of the World’s Women” exhibit in 2000.
Collage artist and author Marianne Sade, a member of the Chestertown Public Arts Committee, says she delights in observing public reactions to the art—from children patting the heads of the “Wolves” to lively debates over the meaning or message behind a particular piece.
“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—just as their creator, Sally Matthews, envisioned them—I was reminded of the initial concerns of a few locals that the lupine figures might scare young children.
But as I approached the pack, a chubby-cheeked preschooler let go of his mother’s hand and ran gleefully toward the lead wolf, looking straight into its squinted blue-gray eyes, and gave it a long hug.
Things to Do in Chestertown
Pick up a walking tour map for the Woicke Sculpture Collection at the Kent Cultural Alliance site (101 Spring Ave.) or the Kent County Public Library-Chestertown (408 High St.). 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 by kentcounty.com, is available at area inns.
Carla Massoni of Massoni Art (113 S. Cross St.) collaborates with architects, interior design firms and art consultants to curate artworks in settings ranging from corporate offices and SoHo lofts in New York City 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 (241B High St.) is a gallery, working art studio and teaching space helmed by a contemporary realist painter whose portraits are rendered in oil, pastel, charcoal and graphite.
At Hegland Glass Studio (315 High St., Suite 103), founders Patti and Dave Hegland specialize in kiln-formed art glass, including intricately colored bowls and platters.
Discover rising artists at the Kent Cultural Alliance at the Raimond Cultural Center (101 Spring Ave.), 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, 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, 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 and strolling musicians, as well as 5K and 10-mile runs.
The National Music Festival, coming 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 (337½ High St.) 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 (208 High St.), helmed by chef and owner Steve Quigg, serves seasonal farm-to-table (and water-to-table) fare, including a Sunday brunch.
Evergrain Bread Co. (201 High St.) is a carb-lover’s heaven specializing in fresh breads, including rustic sourdough and flaky croissants. Grab a loaf for takeout or linger over pastries and good coffee.
Brewpub and distillery Bad Alfred’s (323 High St.) hits the spot with wood-fired pizza, including a deep-dish option, craft beer and a popular crab dip.
Where to Stay
Set on 35 acres of lush landscaping, meadows and woodsy paths, Brampton 1860 (25227 Chestertown Road) is less than two 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.
White Swan Tavern (231 High St.) is a short walk to the town’s galleries and restaurants. Its new owners 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 to enjoy in the dining room or outdoors on the patio or front porch.
For a peaceful bayside stay, the recently renovated Great Oak Manor (10568 Cliff Road) offers elegantly appointed rooms, suites and a two-bedroom carriage house with waterfront views.
Christine Koubek Flynn’s travel and arts stories have also appeared in The Washington Post, Coastal Living and Bethesda Magazine.