Issue: From the Chesapeake Bay Magazine Archives
Destination: Chestertown, MD

At first glance, Chestertown looks like so many other leafy, brick-lined 
historic Bay ports. But this vibrant, international town  is much more than 
the sum of its parts. [October 2003]

By  Wendy Mitman Clarke 

Photograph by Michael C. Wootton 

The deep, thoughtful walls of the White Swan Tavern in Chestertown, Md., are an antidote to humidity and bewilderment. The innkeepers serve afternoon tea here from three to five, and though I had stopped in with uncertain, high-summer expectations (Tea? When it's 90 degrees out?), I was delighted to find iced tea (as well as hot), lemonade, cookies, cakes and, best of all, the ponderous quiet of a very old building's thick, cool walls. The room where tea was served had the sweet dense smell of wood smoke, instantly conjuring thoughts of crisp autumn evenings. At a table next to the window, a couple talked quietly over a wood-inlay chessboard and a basketful of pawns and knights. I sipped lemonade and let the place calm my flustered brain like a steady rain settles the waves.

I had just come from the nearby studio of Robert Ortiz, where the Latin rhythms of Ruben Blades combined with the squeal of a router--a duet that, defying all logic, worked. It could be an aural metaphor for Ortiz's furniture, a combination of ritualized Japanese line and curve and Shaker simplicity and functionality. "The marriage of two seeming opposites," Ortiz says. It's a union he has honed for years, and which last year won him Best New Artist at the Philadelphia Furniture and Furnishings Show, juried by Fine Woodworking magazine--akin to winning at Westminster, or slamming one over the Green Wall at Fenway during the World Series.

Tightly knit, with a salt-and-pepper beard, Ortiz works out of a former abandoned feed mill three blocks from the Chester River. His office, where neat stacks of cherry ruminate in the dark in back, sits in what was the grain elevator. "Before they put the apartments above, you could see up four stories," he says, clearly regretful about the lost heavenward view. Ortiz's family is from the island of Villeques off Puerto Rico; he grew up in New York's Greenwich Village, where he entered a Catholic religious order at the age of 14. Later he also studied music, taught high school Spanish literature and theology, and renovated houses. Then he read George Nakashima's The Soul of a Tree, which focused his inquisitive, free-range mind on a Japanese furniture aesthetic. Renovating houses wasn't furniture making, though. So he sought further education. "The only books that made sense to me were on building Shaker furniture," he says. "It was simple enough that you didn't need a lot of fancy tools."

So, how weird is it to find in Chestertown--a town of 19,000 bordered by winter wheat, corn and a swift brown river--a philosopher Puerto Rican from New York whose stunningly beautiful Japanese-Shaker work has drawn the attention of woodworking's finest? Well, consider this. Just inside the front door to Ortiz's studio, beneath a bloom of Japanese lanterns, is an elegant, open structure made of cedar and light and soul.

Ortiz created it so that Maiko Behr, daughter of Chestertown ceramicist Seiko Behr, could perform a formal tea ceremony on High Street outside the gallery where her mother's work was about to be shown. And so it happened. "I thought, wow, isn't this great!" Ortiz says, remembering the dozens of people who gathered to witness. "Here we are on the Eastern Shore in Chestertown doing a tea ceremony on the street!"

Great, indeed. And a little bewildering. I sip my lemonade and breathe in the cool, colonial air of the White Swan Tavern, built in 1733, trying to figure out just where I have landed. After a bit I'm drawn to the next room, where, in a glass case along one whole wall, are displayed some of the 50,000 artifacts archaeologists excavated here 25 years ago while preparing to restore the property to its 1790s state. Here is a set of 300-year-old ice tongs (found in the well), brass stirrups from sometime around the American Revolution, an iron stirrup from as early as 1650, a pipe bowl from 1730 decorated with Royal Arms. And oh yes, a slipware charger dated 1730--made in the North Devon District of western England (the sgraffito swan in its center is now the inn's logo), the only such example of its kind ever found in the United States. George Washington visited here, probably around the time he was handing over 50 guineas to help the Reverend William Smith found Washington College in 1782.

So, sure. A town where the nation's first president hung out and gave his name to the first college chartered in the nation, where the unmarred architecture spans nearly 300 years and the boxwood gardens smell of nothing so much as moist stone and permanence, where history oozes between the cross-hatched bricks as you walk down High Street beneath 100-year-old trees, the river glittering in the near distance. If it were only about its history, Chestertown would be perfectly one-dimensional and simple to hold in one's brain--easy to visit for a day and file away with all the other venerable burgs around the Bay where George slept or ate or changed his socks. But then you find someone like Bob Ortiz or Seiko Behr, and you quickly realize as you walk these shady, historic streets that you can't swing a wet cornstalk without hitting an artist of regional or national renown. The town is home to four artist's organizations (plus a restored vaudeville theater), and dozens of people are listed on the county website under "directory of artists and craftspeople"--sculptors, painters, photographers, potters, performers, woodworkers, metalworkers, fabric and textile and stained glass artists, jewelers, musicians. It is also home to a highly innovative new scholarship center that this year hosted two dozen Islamic college students to learn American history and foster dialogue on Islamic-American relations. There's talk of starting a cricket club, and if you want to join a French conversation group, you can do that here too. Spend a little time in C-town, as they call it, and you begin to ask yourself, just what is going on over here beside these fields of wheat, along this wide ribbon of river?

actually, I wasn't looking forward to sailing there. I knew that sea captains centuries ago negotiated the wily, twisty, fast-running Chester River to dock at Chestertown, a colonial port of entry that became the Kent County seat in 1706. Goodness knows they didn't have a Yanmar under their poop decks to help them along when the full-moon tide started rolling. It's 26 miles from the river's mouth off Love Point to the town dock, and that's a long way in fluky winds and four knots of contrary current. Probably, they timed their arrivals carefully. My family and I didn't, but still I was surprised at how lovely a sail we had upriver, since I had expected little more than a long-distance motor-slog. We left Annapolis late one afternoon and sailed to the Corsica River, about halfway up the Chester, by nightfall. Next morning, despite an adverse current, we flew upstream. With the breeze either behind or abeam of us most of the way, it took only three hours (with occasional help from the diesel) to reach Chestertown--where the graceful old waterfront homes greeted us as they have greeted mariners for generations.

It helps to be fluent in Flemish bond and glazed headers to truly appreciate this town's remarkable architecture, and the chamber of commerce provides a handy glossary in its brochure featuring a walking tour of the historic buildings. But discerning pediments from pilasters isn't really required. Beauty is beauty, whether you know its name or not. There on the riverfront is Widehall (Georgian style), built around 1770 by Thomas Smythe, a politically connected merchant and shipbuilder who headed Maryland's Revolutionary provisional government from 1774 to 1776. There is River House (Federal style), circa 1780s, whose paneling and woodwork from a second-floor parlor were removed in 1926 to be displayed at what is now Winterthur Museum near Wilmington, Del. There's the Hynson-Ringgold House (Greek Revival), built in two sections in 1743 and then 1767, and, since 1944, home to Washington College's presidents. The woodcarver William Buckland in 1772 installed a paneled parlor and grand antler staircase, and in 1932 the interior of one room was removed to the Baltimore Museum of Art.

And there is the Custom House, just up from the town dock and a block from Chestertown Marina where we tied up for our stay. The original building is no longer, but the one still standing will do; it was built in 1746 by Samuel Massey and has the aforementioned Flemish bond and glazed headers. In 1749 Massey sold the building to Thomas Ringgold IV, a lawyer and merchant heavily involved in the West Indies trade. In the late 19th century, when economic times slowed Chestertown to a depressed crawl, the building became an apartment house. Eventually, local preservationist Wilbur Ross Hubbard (who lived in Widehall, across the street) bought the building in the 1970s and, with money from the Maryland Historic Trust, restored much of its original detail. When he died in 1993, he gave it to Washington College.

Now on the National Register of Historic Places, the Custom House is home to the college's C.V. Starr Center for the Study of the American Experience--a new forum for scholarship on American history. The center was a radical step for the college, says its boyish, enthusiastic director, Ted Widmer, because it was off campus (the main campus is just beyond downtown proper) and not directly related to any department. "But I think everyone agrees it was a good step," he says. "It's part of growing and offering more to the students. . . . We're very interested in hands-on history, getting out of the classroom, touching artifacts, feeling the air on your face."

To that end, students helped in the archaeological dig at the Custom House in 2000 that preceeded its most recent restoration. Some of the results of that dig--and subsequent explorations at the birth site of Harriet Tubman in Dorchester County, excavations at the Hermitage slave quarters in Queen Anne's County, and even underwater archaeology in the river--are on display in the Custom House's basement, where a 1,600-square-foot archaeology lab is open to the public. Displays throughout the various rooms outline how excavations are conducted, and artifacts are front and center (one room, clearly once a kitchen, uses an original walk-in fireplace as exhibit space). During our visit, students were sweating through an exam, but one of the instructors was happy to let us explore a long, narrow, arched cellar that stretches from beneath the building toward the street. "Cool, a dungeon!" my son Kaeo yelled, and indeed that's pretty much what it looked like with its iron gate and iron rings dangling from the brick walls and ceiling. Theories abound about its use (prison, slave-holding, smuggling), but the most likely one is it was a place to store wine and other goods off-loaded from ships.

Beyond archaeology and history, though, the Starr Center is about the exploration of broader themes and ideas, Widmer says. "We love history, but we're very interested in the world of action, both the policy world and how you can shape a better world through good lectures and programs, and dialogue between different people," he says. An example of the center's innovative role happened this summer, when the U.S. Department of State asked it to develop a program to bring 21 college students from the Islamic world to Chestertown. "It's the first attempt to do this under the State Department," Widmer says. The students--from India, Pakistan and Bangladesh--spent four-and-a-half weeks studying American democracy. They combined intensive classroom seminars with field trips, starting with Chestertown's local government and judicial system and ending with trips to the Supreme Court and the Capitol in Washington, D.C., as well as meetings with Colin Powell and Bill Clinton in New York City. "We're teaching them American history, but we're talking about current events all day long, and that's exactly the kind of thing the Starr Center likes to do," Widmer says. "It feels fantastic. We're a small college, but we're doing our part to advance dialogue among different people."

it's hard to underestimate the effect that a historic building trek--even an abbreviated one--has on two young children on a hot summer day. Toy stores, new books and ice cream were quickly becoming priorities, so we headed up High Street beneath the shady limbs of oaks, sycamores, maples and one basswood so huge and gentle it reminded me of my long-gone grandfather. It didn't take us long to locate our quarry; the toys at Twigs & Teacups on Cross Street (where I also found some eclectic clothing, housewares and jewelry), the books right around the corner at the Compleat Bookseller on High Street and the ice cream a block away at Stam Drug (which is also, as its name makes clear, a pharmacy). There's no place to sit down at the soda fountain inside Stam Drug, but it's easy enough to take your sinfully rich Hershey's ice cream (no fat-free nonsense here) outside to eat while sitting on a nearby bench, which is also a fine place for sipping a vintage root-beer float. "I think," my husband Johnny said, finishing off the last frothy swig, "that I haven't had one of those in thirty years."

One of the best things about Chestertown for visiting boaters is that walking gets you everywhere you need to go--and the walking itself is a treat. Chestertown is lovely. There is precious little ye olde anythinge. There's a local competition to see who can create the prettiest gardens in front of their homes and businesses, so what might be an ordinary sycamore tree in any other town is the centerpiece of a profusion of hostas and exotic blooms. Quiet, shady porches are adorned with wicker in all its forms, and secret gardens whisper and beckon from behind 200-year-old homes. A steady chorus of songbirds drowns out most traffic, and from the cusp of High Street, about two blocks up from the town dock, the river glitters on and on.

More than anything, this town feels like a neighborhood. Flop into one of the comfy chairs for a poetry reading or a sandwich at Play It Again Sam--a funky little cafe on Cross Street decorated with brilliant colors and artwork--and you are bound to see people you know. "You can't turn left without meeting people to talk to," says Kathleen Moore, the executive director of the Prince Theatre Foundation, which manages the restored 1926 vaudeville theater on High Street. "We have a downtown social scene that's very busy."

"I liken living in Chestertown to living in Greenwich Village in New York," Ortiz says. "You know, every neighborhood in New York is four blocks long."

"When I first came here I thought I had died and gone to heaven," says Carla Massoni, owner of the Carla Massoni Gallery and longtime art collector. "This little town has so much richness."

Undoubtedly, this intimacy has helped foster the community of artists and artisans that is blooming as profusely as the flowers. It is this crucible of ideas and cross-pollination of talents, coupled with a truly driving grassroots passion and some deep local pockets, that made possible the funding and construction of the Sultana, launched in 2001. The 59-foot schooner was built in a shipyard downtown (where you now can take in a Shakespeare play during "The Bard in the Yard" series), captivating the locals, who turned out in droves to help fund and build the vessel [see "It Takes a Village," October 1999 and "Splash," July 2001]. Today, the ship is moored on the waterfront and serves as a floating classroom and ambassador for the town. But if Sultana is the most visible and mobile expression of the arts here, it is merely the tip of the brush. Within a three-block area downtown are some 13 studios and galleries. Among them are four arts organizations, and that doesn't include the Prince Theatre, which Moore characterizes as more a performing arts center than simply a theater.

"We [had] forty-five people signed on the studio tour this year. We had nineteen or so last year," says Lollie Sherry, a board member and founder of Chester River Artworks, which annually sponsors the Fall Artists' Studio Tour, an open house for artist studios. "It's really exploding."

"It's really been an effort of people understanding the nature of supporting art in a community," says Leslie Raimond, executive director of the Kent County Arts Council. Many people credit Raimond with being the green thumb who put the Miracle-Gro in the local art garden. She has managed to unite the disparate--and sometimes fractious--groups to cooperate in advancing local arts and making them open to everyone. And Raimond also pursues art in places that others have overlooked; recently, for instance, she has been exploring one of the area's most underappreciated but profound traditions, the gospel singing in local African-American churches.

Carla Massoni agrees that community support is key to what is happening. "The arts don't flourish because of galleries," she says. "The arts flourish because there's a mandate from the people, from the government, because people realize it matters."

From there, it gains its own momentum. People visit the town and are amazed at the breadth of art here, and many of them want to become part of that. "I was a New York gallery rat and I just couldn't believe that work of this quality would be in a little backwater town in Maryland," says Larry Schroth, who directs Massoni's gallery, has a master's in arts education and is an accomplished jazz pianist. "People here have an amazing array of skills. Yesterday we had a closing for a man whose passion is wildlife photography, but he also has a PhD in microbiology, and a law degree."

"This area has many of the same attributes that created other great arts communities, like Sausalito," says Lollie Sherry. "It's charming, it's laid-back, it can be secluded but you can find friendship with like-minded people."

"And," says Gia Campana, a sculptor who is president of Chester River Artworks, "it's on the water."

Ah yes, the water. By Saturday morning, an unusually high tide has swelled the river well over the bulkhead at the marina and into the foot of Cannon Street, where Lucy, the town goose, and a quorum of mallards are conducting some sort of noisy convention. We slosh through the parking lot and head for high ground in town, where the Chestertown Market is in full swing. The little street of Park Row next to Fountain Park is crowded with trucks and vans spilling with goodies--fresh vegetables, huge buckets of colorful flowers, bins of fragrant basil and rosemary. There are rose bushes, herbs and perennials for planting, as well as cut flowers, fresh eggs and honey, even a table of soaps and lotions. People wander with their dogs, sip coffee and exchange news, while kids splash their hands in the fountain, throw pennies in to make wishes and cool off beneath the magnolias and willow oaks.

Our first stop is with the Lapp Family Bakery. I give serious thought to the lemon sponge pie but ultimately pass, knowing it cannot touch my own mother's (heaven and sin in one mouthful, a theological puzzle on a fork). We settle for two gingerbread whoopie pies, half a pumpkin pie and two cinnamon apple dumplings. A little farther on I buy a block of cheddar from Nancy Nunn of Eve's Cheese, a two-family operation that began as a 4-H project. Nunn's two daughters lease cows from Fawnwood Farm in nearby Worton, Md. The farm primarily has Jersey cows, Nunn tells me, but there are also Holstein, Ayrshire, Guernsey, Brown Swiss and Milking Shorthorn. The blend of breeds, she says, helps give their cheese its wonderful flavor. If speed of consumption is an indicator of quality, then this might be the best cheese my family has ever eaten. Last but not least, a bouquet of flowers for the boat from one of the many flower vendors, and we are on our way.
Early the next morning, as new-day sun flickers off the water and polishes the old captain's and merchant's houses a soft gold, we eat the last apple dumpling and tidy the boat. Flush with the full-moon tide, the Chester River has turned its considerable energy toward the Bay, its brown water sluicing downstream, creasing itself against the marina's pilings. We cast off our lines, set the sails and silently join the river, and the thousands of sailing vessels who have gone before us, bidding Chestertown farewell.

Like many Eastern Shore towns, Chestertown has had an uneasy relationship with one particular part of its past--the legacy of slavery, and the results of its abolition at the end of the Civil War. But there is a project afoot in Chestertown that, its supporters hope, will help make that past easier to understand and to reconcile with the present.

The focus of the project--a tall, boxy building two blocks up from the water in a neighborhood known as Scotts Point--doesn't look like much at the moment. Clad in red-and-white flecked tarpaper over the original wooden clapboards, roof open to the sky in some spots, it is covered with ivy and boarded up. But for decades, this was the proud home of the Charles Sumner Post of the Grand Army of the Republic (GAR), built by freed slaves from Chestertown and Kent County who fought for the Union as members of the U. S. Colored Troops (U.S.C.T.). There's only one other building like it still standing, in South Carolina.

During the Civil War, some 8,000 slaves and free blacks from Maryland enlisted or were recruited into the U.S.C.T. About 400 came from Kent County. After the war, veterans formed the Grand Army of the Republic, similar to today's VFW. "The GAR was the only integrated social institution in the United States in the nineteenth century," says Kees de Mooy, program manager at the C.V. Starr Center, which is helping shepherd the Sumner Post restoration. Many GAR posts were either white or black, but some included both races, and whites could not prevent blacks from establishing their own GAR posts. Black GAR veterans were encouraged to participate in national GAR meetings and parades. In all, 22 black posts operated in Maryland.

The Sumner Post was established in 1882, though its members did not build their hall on South Queen Street until 1908. They met weekly, supported veterans' families and conducted patriotic celebrations. The most important was Decoration Day, May 30, when the Sumner Post members would parade with brass bands, family members and friends, place wreaths on the graves of Civil War dead in the town's white and black cemeteries and throw a wreath into the Chester River to commemorate those who died at sea during the war. Once the actual building went up, it became a focal point for the black community in Chestertown. Meetings were held there, receptions, graduations--and concerts. In 1938, when "A Tisket A Tasket" was a national hit, Ella Fitzgerald performed on the second floor stage with Chick Webb and his orchestra.

The stage is still there. So is the original paint--dark red on the wainscoting, white on the upper walls and blue on the ceiling. About a year ago, the developer who owned the building was ready to demolish it when a coalition of Chestertown residents--led by a local group called Preservation Inc., and historians from Washington College and the C.V. Starr Center--persuaded him to spare it. With a $50,000 grant from the Maryland Historic Trust and $10,000 more from local historic organizations, Preservation Inc. bought the building. In July, the National Trust for Historic Preservation gave a $19,000 grant to begin the building's stabilization and restoration.

De Mooy expects the Charles Sumner Post to reopen within two years, and part of it will be dedicated to telling the story of Maryland slaves who went to war. "Here is a building run down to the point where most people would bulldoze it," de Mooy says, "but there is this amazing story just underneath the surface, about men who gave their lives and whose stories have not been told. Not nearly."

Getting to Chestertown by boat is straightforward; cruise up the beautiful Chester River until you see the town on the river's western side, 26 miles up from the Chester's mouth at Love Point. If you hit the bridge you've gone too far. The river is well marked and deep within the channel--at times our depthsounder registered 50 feet--but don't stray, or you may quickly find the bottom. It helps to catch the tide; it runs as quickly as 3 to 4 knots and can slow or speed your trip considerably. The farther north you travel, the more rural and quiet the riverscape becomes. On our way downstream after leaving Chestertown we set sail in the early morning, and the only sounds on the upper river were songbirds along its banks and ospreys overhead.

Many boaters anchor off the riverfront and there's plenty of depth to do so. Just remember that current, and be sure to set an anchor that can handle the 180-degree switcheroo. You may see the schooner Sultana tied up at the foot of Cannon Street. Dinghies are welcome to tie up here (at the small floating dock attached to the main dock). You may also tie up a dinghy to the town dock at the foot of High Street, but the access can be difficult, depending on tide. Also, just south of town is Wilmer Park, a public park that's within easy walking distance of downtown. Transients may anchor off here and dinghy in, tying up at the bulkhead in front of the pavilion. Visitors can also reserve a slip, as we did, at Chestertown Marina, or next door at Scotts Point Marina.
For more information about Chestertown and a list of annual events go to or

Chestertown Marina (410-778-3616); gas and diesel, overnight slips, electric service, showers, laundry facilities, launch ramp, 25-ton boat lift, engine repairs, ship's store, pump-out ($5), and Old Wharf Inn restaurant.

Scotts Point Marina (410-778-2959); overnight slips, electric service, showers.

Andy's (410-778-6779), 337 High St.; tavern and sitting room with live entertainment, open Monday through Saturday
at 4 p.m.

Blue Heron Cafe (410-778-0188), 236 Cannon St.; open Monday through Saturday for lunch and dinner.

Crystal Decanter (410-810-1701), 337 High St.; wine, cheese and dessert, open noon–8 p.m. daily except Wednesday.

Feast of Reason (410-778-3828), 203 High St.; gourmet soup and salads, open Monday through Saturday 10 a.m.–4 p.m.

Imperial Hotel and Restaurant (410-778-5000), 208 High St.; open for dinner Wednesday through Saturday; lunch on Sunday noon–3 p.m.

Kettle Drum (410-810-1497), 117 S. Cross St.; traditional English tea and light fare, open Friday and Saturday 10 a.m.–8 p.m.; Sunday 10 a.m.–4 p.m.

La Ruota (410-778-9989), 323 High St.; open Wednesday through Saturday for lunch and dinner.

Old Mill Bakery and Cafe (410-810-8841), 207 S. Cross St.; open Monday through Saturday, 10:30 a.m.–7 p.m; Sunday 11 a.m.–5 p.m.

Old Wharf Inn (410-757-1467), at Chestertown Marina; open daily year-round for lunch and dinner. Dockage for diners.

Play It Again Sam (410-778-2688), 108 S. Cross St.; coffee shop and light fare, open daily for breakfast and lunch.

The Arts
Carla Massoni Gallery (410-778-7330), 203 High St.,

Chester River Artworks (410-778-6300), 306 Park Row. Open Thursday through Saturday. Artists' work for sale; classes for all ages in various media. Visiting boaters who would like to schedule classes should contact Lollie Sherry at the number above. (See for a list of classes.)

Chestertown Arts League (410-778-5789), 312 Cannon St. Juried shows, exhibits, arts classes.

Ehrman Tapestry (410-810-3032), 112 S. Cross St., Textile and needlework workshops and kits.

Imagination Alley (410-778-9678), 337 High St., www.chestertown/imagination alley. Classes in a range of art forms for youngsters from 2 to 18.

Kent County Arts Council (410-778-3831), 101 Spring St., Regular exhibits.

Pottery By Seiko (410-778-1498), 100 S. Queen St., call first.

20 Robert Ortiz Studios (410-810-1400), 207 S. Cross St.,

Vicco Von Voss Furniture Design (410-810-0267), 206 S. Cross St.

Woodcarvings Etc. (410-810-7999), 308 Park Row.

Special Attractions
Geddes-Piper House (410-778-3499), 101 Church Alley, This 18th-century brick townhouse, the Historical Society of Kent County headquarters, includes portraits, antiques and period furniture. Guided tours Saturday and Sunday 1–4 p.m., or by appointment. Self-guided tours weekdays.

Prince Theatre (410-810-2060), 210 High St., This beautifully restored vaudeville theater offers movies and performances for all ages.

Schooner Sultana (410-778-5954), docked at the foot of Cannon St., office at 105 S. Cross St. Public sails, call for reservations.

Hill's Inn (410-778-1926), 114 Washington Ave.

Imperial Hotel and Restaurant (410-778-5000), 208 High St.,

Parker House (410-778-9041), 108 Spring St.

White Swan Tavern (410-778-2300), 231 High St.,

Widow's Walk (410-778-6455), 402 High St.