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Chestertown: Reimagining a Historic Shore Town

Oct 13, 2017 09:00AM

Hebe, the Greek goddess of youth and rejuvenation is represented as a statue in Fountain Park, one of the town’s central gathering spots. Photo by Tony Lewis, Jr.

By Mary Lou Baker

We call Chestertown the center of the universe,” says resident Carla Massoni, explaining that the term is an “inside joke” among some Kent County folks. In some ways, they’re spot on.

After spending a few days in this historic town on Maryland’s Upper Eastern Shore, the claim seems much less far-fetched. Its downtown shops are doing well, the County is leveraging the arrival of state-of-the-art fiber optic cables, the town is completing an ambitious waterfront park initiative, and Washington College is breaking ground on a $5 million expansion of its boating facilities on the Chester River.

Two years ago, Chestertown was honored with the state’s coveted designation as an Arts and Entertainment District. “Small rural communities need to reinvent themselves to give new meaning to their identity,” says Massoni, who has high hopes for the future of her adopted hometown. “Change is happening all over the country, with the expansion of Amazon and malls closing. We see changes on the horizon and are responding.”

Local artist Carla Massoni, owns a popular gallery on High Street. Photo by Tony Lewis, Jr.

Massoni, who owns two art galleries in town, credits widespread community pride for the interactive cooperation of local leaders, giving as examples the Greater Chestertown Initiative and the Downtown Chestertown Association. She is an enthusiastic cheerleader for the arts as a catalyst for local economic development, especially now that the town’s Arts and Entertainment District has appointed John Schratwieser as the new head of the Kent County Arts Council. The Council will renovate the former “town arts” building for conferences, retreats, and arts-related activities. “There are so many wonderful arts organizations and artists of all kinds in our county—our goal is to help them thrive,” says Schratwieser, a former Chestertown resident who spent the past seven years as director of Maryland Citizens for the Arts.


Getting There



Chestertown is a place that has become a favorite destination for me and my chocolate Labrador retriever. This is a dog-friendly town, complete with a dog park and a few “pet-friendly” tables at the town’s restaurants. There are places to stay overnight and a fine choice of restaurants and cafes for breakfast, lunch, and dinner. Festivals mark every month, especially in October when the locals celebrate the world of Harry Potter and sailors flock to the waterfront for Downrigging Weekend, an impressive gathering of tall ships and wooden boats. Every day is party time in Chestertown—and the guest list includes folks from anywhere who want a taste of history and the comfort of feeling like they have found a “hometown.”
Chestertown brims with colonial charm and Maryland pride. Photo by Lisa J. Gotto
Getting to Chestertown from “somewhere else” is a pleasure in itself. Escape the high-speed lanes of Route 50 and ease onto winding Route 213, one of the Eastern Shore’s more scenic thoroughfares. Blink your eyes and you’ll miss the town of Centreville, but stay alert to the bucolic sweep of farmlands that eventually give way to some roadside businesses and finally the rustic bridge that crosses the Chester River. Look to the shoreline for the sight of beautifully maintained historic homes fronting the water, promising yourself a closer look on the popular historic homes tours.

I have met several people who claim that crossing that bridge was a magical experience—a magnet that drew them into the net of the Chestertown community. That could be hindsight on their part, although I personally can relate to that theory. For first-time visitors, I suggest you take a left on Cross Street and stop at the Visitor’s Center next to the Town Hall where the staff are reliable and friendly and can provide helpful sources of information, including a charming map of downtown.


Walking Shoes



Getting to know this remarkable town and its friendly residents is easy: just park your car, leash your dog, and walk along Cross Street to Fountain Park. In many ways, the park is the heart and soul of the town—symbolized by a magnificent fountain in place since 1899 that is crowned with a graceful likeness of Hebe, the Greek goddess of youth and rejuvenation. Kay MacIntosh, the charismatic coordinator of Chestertown’s Arts and Entertainment District, has adopted Hebe as the symbol for the town’s dynamic merging of the old with the new.
Washington College has been a town beacon of education since 1782. Photo courtesy of Washington College.
Folks come to Fountain Park from as far away as Philadelphia for the Saturday Farmers’ Market, held from mid-March to December. Created by the Ladies Improvement Society (now the Chestertown Garden Club), the park is also the scene of free summertime concerts. Chestertown loves all kinds of music; there’s even a robust ukulele club. But classical music takes center stage for the first two weeks of June, when The National Music Festival at Washington College showcases the talents of young musicians from all over the world.

Opposite Fountain Park is the Historical Society of Kent County, recently relocated to the historic Bordley Building on the corner. Check out the educational window displays and expect a friendly welcome as you walk in the door—even if you interrupt a board meeting, as I did late one weekday afternoon. Steve Frohock, Barbara Jorgenson, and Kurt Smith graciously postponed the business at hand and told me about their town’s history as if the 18th century was yesterday. They invited me to browse among the exhibits and books for sale, one of which is a buy-worthy illustrated inventory of Chestertown’s historic sites, each with a fascinating mini-history tracing them back to the 18th and 19th centuries. Frohock proudly pointed out that Chestertown’s stock of historic homes is second only to the architecture in Annapolis.
Opportunities to be creative abound in Chestertown. Pictured, Mike Pugh, manager of the RiverArts Clay Studio. Photo by Tony Lewis, Jr.
Jorgenson gave me a brochure on African American History with an easy-to-read map featuring descriptions of 29 sites dating from the 1700s to the present. The brochure was produced by the Society’s African-American Community History Project with assistance from the Kent County Diversity Dialogue Group. My serendipitous stop at the Bordley House was an educational one that I recommend to anyone visiting Chestertown.


Browse, Buy & Brunch



Feeling like I had made three new friends, I wandered next door and met Marjorie Adams, owner of Mimi’s Closet, an upscale apparel and jewelry shop. Upon learning I was an Annapolitan, Adams told me she had recently hosted a group of six women from Eastport for a private Sunday afternoon “sip and shop” party. Promising to return to Mimi’s when I was “off duty,” I stopped to browse in The Finishing Touch, where owner Bob Ramsey’s inventory rivals any big city art supplies shop, with a notable selection of clever greeting cards and unique gifts. Next door, Michelle Timmons provides stylish clothing for women, as well as costume jewelry, books of local interest, select menswear, and gift items. Her Dockside Emporium celebrates its 20th anniversary this year and is considered a Chestertown institution.

Later, I dropped into She She (next door to an amazing garden/florist shop called Bloomin’ Wild) I was greeted by its personable proprietor, Christine Tilghman. “Look what I found at the Crumpton Auction,” she said, pointing to a rustic table and a handsome teacart. Fun and friendly, she looked around the shop and seemed surprised that she was now the owner of what had been a quirky something-for-everyone place called Poor Richard’s. Former owner Richard Keaveney had promoted his shop with the humorous tagline “Nothing Over a Million Dollars.” I continued my exploration with an amble along Cross Street, lined on both sides with interesting specialty shops. There are treasures to be found in Tom Martin’s Book Plate, a used bookstore with an inventory of 400,000 volumes and a gift section featuring colorful pottery from Spain and Portugal. While Book Plate has been a Chestertown fixture for 13 years, the Chester River Wine & Cheese Co. across the street is a newcomer. Co-owner John Laucik, a former management consultant from Philly, said he had “stalked” the Eastern Shore for several years before settling on this location. He stocks 50 to 60 cut-to-order cheeses, pates from Tartania and Trois Petite Couchons, pastas and specialty gourmet items from Philly and personally selects the 60 to 70 wine labels chosen to appeal to his clientele. Laucik partners in the wine and cheese shop with his wife Jennifer Baker, also a former management consultant. Together they run it and another business just down the street—a delightful specialty shop called Welcome Home. Should you decide to take a tour, two other stops you will want to consider are Twigs and Teacups, which locals consider the best gift shop in the world, and its neighbor, Create. Just two doors up, Create is a beautiful new artisans gallery founded by Massoni and featuring the work of six local artists.
“Mr. Fix-It” and business owner, David Hoatson is proprietor of Chestertown Electric, a shop of nostalgic electrical finds including rotary phones, transistor radios, and vintage fans. Photo by Tony Lewis, Jr.
And you can expect the unexpected in Chestertown. Guys, especially, will be fascinated by David Hoatson’s little gem on Cannon Street, Chestertown Electric; a source for an eclectic variety of antique electric appliances. Visitors to his shop will see history for sale in the form of a 110-year-old piano lamp, a 1918 electric fan in perfect condition, and one of the world’s oldest ceiling fans, made in India circa 1894.

Breakfast, lunch, and dinner are indoor sports in Chestertown, where every eatery has its own special appeal. The liveliest places in town are the nest of restaurants lovingly overseen by owner J. R. Alfree. “Life is short. Break the rules. Forgive quickly. Love truly. Laugh uncontrollably. Never regret anything that makes you smile,” says the sign prominently displayed at his Lemon Leaf Café, located next door to his casual Past Time Pub and wee ice cream shop called Treats. Chances are you’ll see J.R. checking to see if everything’s “Just Right.”
Mom-and-pop-type shopping opportunities include galleries, a fine wine and cheese purveyor, and gift shops to please any collector. Photos by Tony Lewis, Jr.
There are plenty more delicious options in the walkable downtown district. Join the locals for breakfast and lunch at Evergrain Bread Company for remarkable muffins and pastries; discover Figgs Ordinary, specializing in gluten-free fare; and enjoy the ’60s vibe at Play It Again Sam, which serves breakfast and lunch at indoor or outdoor tables. Fish Whistle, a tried and true establishment popular with tourists, is the town’s only waterfront restaurant and offers lunch and dinner. Find praise-worthy lunch, dinner, or Sunday brunch at The Kitchen at the Imperial Hotel and fine dining at the well-regarded Blue Heron.


Mainstays & Upgrades



Speaking of the unexpected, the genre is alive and well at the Garfield Center for the Arts in the heart of the historic district. This notable theatre is the scene of plays, concerts, and special events and serves as the hub of Kent County’s lively arts scene. Writers, critics, actors, and anyone interested in the performing arts are invited to gather on the first Monday of every month for a meeting of the Live Playwrights Society, and the Open Mic Night held every last Wednesday, welcomes music, poetry, comedy, and… whatever. There also are summer music and theater camps for kids, a Roots music series, and no end to the creativity at this remarkable Chestertown gem. Find out more online.
Owners of two shops on Cross Street; Chester River Wine & Cheese Co. and Welcome Home, John Laucik and Jennifer Baker. Photo by Tony Lewis, Jr
Make time for a visit to the Sultana Education Foundation located where Cross Street curves toward the river, especially if you have young children in tow. It’s the first LEED platinum building on the Eastern Shore and was the subject of its own feature in What’s Up? Eastern Shore in April of 2016. The Sultana Education Foundation, a private nonprofit that provides hands-on educational opportunities for more than 5,000 Maryland students and teachers each year, many include experiencing the full-scale replica of the 1768 British schooner, Sultana, the organization’s namesake.

Boats are part of Chestertown’s heritage as a historic port, and a key component of Chestertown’s re-invention strategy is the Chestertown Waterfront Initiative, now in its second phase of restoring the town’s history-rich waterfront. Boosted by $1.1 million in new state funding on top of earlier grants from the USDA and the Maryland Heritage Areas Authority, the Town has purchased a commercial marina that had fallen into disrepair, created a waterfront master plan, completed some dredging, reconstructed bulwarks and a boat ramp, and built a pedestrian walkway. Ultimately, the revitalized waterfront will include a 70-slip deep-water marina, a waterfront plaza, and a 7,000-square-foot building with showers for boaters, a marine store, and a second-floor interpretive center, and community meeting space.
Furniture artisan Bob Ortiz of Robert Ortiz Studios. Photo by Tony Lewis, Jr.
Another strong component of Kent County’s transition into the future is the addition of a high-speed fiber optic network that will bring a remarkable Gigabit of Internet speed and enhanced WIFI access to local businesses, institutions, and residents. “The ability to offer businesses and residents such a broad range of options for Internet use is extremely important in a rural community such as Kent County,” says county economic development director Jamie Williams. “We have quality of life covered,” says Walker. “Now we are building our quality of opportunities—and fiber optics is a major component of that effort.”

Enhanced Internet will no doubt improve the quality of life for students at Washington College, a 112-acre liberal arts college founded in 1782—synonymous with Chestertown’s reputation as a cultural center. Washington College is deeply involved with the Chestertown community in myriad ways,” says spokesperson Wendy Clarke, citing the schools’ Academy of Lifelong Learning as an example of its value to the community. “More than 370 members participate as teachers or students on topics ranging from politics to music, history, and art.” The program is part of the appeal of Chestertown as a retirement choice, whether independently or as a resident of the local Heron Point community.

Kurt Landgraf, Washington College’s president, is the latest resident of the historic Hynson-Ringold House at 206 Water Street. Landgraf, 70, arrived in Chestertown in June after a decade as CEO of the Educational Testing Service and many years as CEO and CFO at DuPont. He takes office at an exciting time, as Washington College breaks ground for its new Hodson Boathouse, a $5 million facility on the waterfront supported by more than 150 donors, including a $2.5 million gift from the Hodson Trust and a $1 million donation from Regis de Ramel, a member of the college’s Board of Visitors and Governors.
Quality of life in Chestertown includes vibrant theatre productions, comedy nights, and theatre programs for children at the historic Garfield Center. Photo by Jeff Weber
Chestertown is a happening place, with unique events scheduled for most weekends. In-town overnight accommodations include the charming chambers of The White Swan Tavern bed and breakfast (afternoon tea served daily), the historic Imperial Hotel, and the Victorian Hills Inn near Washington College. Nearby are the delightful Brampton Inn and its cottages with fireplaces on 20 wooded acres, and the elegant Great Oak Manor on the Chesapeake Bay with access to a private beach, pool, tennis courts, and a nine-hole golf course.

With an illustrious history dating back to the 1700s, there’s no doubt that Chestertown is poised for its next chapter. With its many supporters, a vital arts-and-entertainment center, and its modern-day twist on hometown appeal, Chestertown is an exciting place to visit—and to live.

There is always something going on in Chestertown! Find our Chestertown Save-the-Date Events blog here.

Today, Community maryland historic chestertown October Eastern Shore 2017
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  • Chestertown Antiques Show & Sale

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    Now in its 54th year, the Chestertown Antiques Show & Sale, set for Friday, November 24th (4–7 p....


  • Festival of Trees - Preview Party

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    Celebrate “All that Glitters” at the 32nd annual Festival of Trees presented by the Friends of Ho...


  • Festival of Trees

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    Kennedy Krieger Institute kicks off the holiday season by welcoming Santa Claus to their winter w...


  • Festival of Trees

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    Kennedy Krieger Institute kicks off the holiday season by welcoming Santa Claus to their winter w...


  • Dickens of a Christmas

    12/01/2017
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    Enjoy a “Dickens of a Christmas” Friday, December 1st through Sunday, December 3rd throughout his...


  • Easton's Moonlight Madness Shopping Event

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  • 54th Holly Ball

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