Reading a cruising article, or most boating articles for that matter, is designed to put you there. If we, your friendly authors, do it right, you can almost taste the salt air, feel the bad weather, moan about the engine problems, and revel in the ice cream cone you found. In short, you feel the simple joy of being a cruising boater.
Our See the Bay articles are designed not just to inform, but also to tempt you to visit. Have I been there? What did I miss or what will I miss by not going? Our goal is that you are enticed to plan a cruise, jump on your boat, and experience the fruits of a cruising visit as outlined in the article.
So, let’s talk about Chestertown, because this place should be on your list!
History
Like so many Chesapeake Bay port towns, Chestertown goes way back to pre-revolutionary days. It was founded in 1706 and named one of six Maryland “Royal Ports of Entry.” The economic boom that followed this designation made the town and many of its citizens wealthy. In less than 50 years Chestertown was second only to Annapolis in port operations in the colony.
Today the town boasts a population of a little over 5000. The wealth produced in the early to mid-18th century is shown in the plethora of brick mansions and townhouses that dominate the waterfront. Not surprisingly, Chestertown is second only to Annapolis in its number of existing 18th-century homes.
In May 1774, five months after the British closed the port of Boston as a result of the Boston Tea Party, the good citizens of Chestertown adopted provisions that prohibited the buying, selling, or drinking of tea. Popular legend has it that they also dumped tea into the Chester River, following Boston’s example. We couldn’t document this, but they do have a Tea Party Festival every year (usually around Memorial Day weekend).
Chestertown is also a ‘college town.’ Abutting the historic district, a short walk from the waterfront brings you to the campus of Washington College, a private liberal arts college founded in 1782. Washington College is the 10th oldest college in the United States.
Unlike so many “Washington slept here” places, our first president had a very distinct involvement with Washington College. He fiscally supported the founding of the college, granted the founders the right to use his name, served on their governing board after its founding, and received a Doctor of Laws degree from the College in 1789.
For more history, visit the Bordley History Center at 301 High Street. A walking tour map (self-guided) is available there.
Visiting Chestertown
One of the most fun parts of any weekend visit to Chestertown is a stroll through an extensive Farmer’s Market. The town dockmaster reports that this attraction alone helps fill his transient slips every weekend. Several blocks of High Street, just a short walk from the municipal marina, are blocked off every Saturday from 8 a.m. to noon to accommodate the market.
Chestertown has a vibrant art community with at least nine art galleries within easy walking distance from the marina. Book a class to make your own art at Art on High or the Kaleidoscope Art Studio or visit the numerous galleries with works by local artists. Galleries include Tish Fine Art Plus, The Skipjack Art Studies, Chestertown River Arts, Hegland Glass, The Artists’ Gallery, MassoniArt Gallery, and The Collection.
You can get yourself lost at The Bookplate, one of the most interesting and eclectic bookstores on the Bay. Here you can wander from aisle to aisle and room to room in this former home that is now packed with books on every subject. Cat lovers can enjoy visiting with Keke, the resident cat, who is friendly and entertaining.
Dining in Chestertown
Play it Again Sam is a local favorite for breakfast and lunch sandwiches. You’ll always find a lot of locals eating there or taking it to go. The Evergrain Bread Company always has a crowd waiting to enjoy freshly baked bread and pastries with a cup of coffee.
Stam’s Luncheonette preserves elements of its 19th-century pharmacy location combined with an old-fashioned ice cream parlor. It is a truly unique setting with a wonderful lunch selection. After lunch enjoy your favorite ice cream or sundae.
The Kitchen at the Imperial provides a comfortable and interesting venue for lunch or dinner for a couple or a group. With a focus on farm-to-table, eating at The Kitchen is an experience that shouldn’t be missed.
Watershed Alley is one of the newer restaurants in town and highlights the Chesapeake Bay watershed. Its menu, offering a variety of seafood and local farm food, receives good reviews.
At The Retriever, next door to the Watershed Alley, you can sample oysters from various points around the Bay. You can also enjoy a variety of appetizers and a small selection of entrees while sampling the huge selection of scotches, whiskeys, and other adult beverages from around the world.
Bad Alfred’s Brewpub and Distillery makes small-batch craft spirits. You can schedule a tasting tour and get a behind-the-scenes look at the process, or just enjoy a wide variety of spirits and other drinks along with their wood-fired oven menu.
Modern Stone Age Kitchen is an award-winning “foodery” featuring scratch-made, artisan food made with local ingredients. More than just a restaurant serving breakfast and lunch, it’s a bakery, grocery store, and food lab where you can take cooking classes focused on reviving ancestral food practices to make nourishing food.
Looking for an upscale glass of wine or tasting flight along with a refined selection of tapas and small bites? Visit Casa Carmen Winery’s Bodega at 312 Cannon Street, just a short walk from Chestertown Marina.
Their tasting room was created in the spirit of the traditional wine bodegas of Spain and South America. The atmosphere is cozy and chic, but with advanced notice they can also handle events for up to 30 people in a private space. Managed locally by Erika and Tyler, this is Casa Carmen’s only location other than a farm in West Grove, PA.
Sweets
Those with a sweet tooth should be sure to check out Bespoke Chocolate where you can get an assortment of handmade chocolate and fudges. For those focused more on ice cream (one of the major food groups), there is Sugar Doodles Sweet Shop and Stam’s Luncheonette.
Coming soon
The 98 Cannon Riverfront Grille at the municipal marina suffered a fire in 2021 and closed. Due to preexisting foundation issues (the restaurant is partly over water), the rebuilding was more than the owners could manage and it was put up for sale. It languished on the market for a couple of years but was recently purchased by a developer. Keep an eye on the site as the plans are for a complete demolition of the current structure and the building of a new waterfront restaurant scheduled to open in May, 2026.
Getting There
Chestertown is about 38 nautical miles from Annapolis. This is an easy two-hour trip if you have a speedy vessel (meaning you could get there after work on a Friday afternoon in summer for a two-night weekend). Don’t let the distance deter you. It is well worth it for the scenery, especially along the upper reaches of the river where it narrows.
The Chester River is well-marked all the way to town. There are two six-knot speed limit areas to watch out for, marked by buoys. The first one is at Rolphs Wharf and Marina, a few miles before reaching Chestertown, and the other is in front of the Chester River Yacht and Country Club, about a mile before town. On our trip in September, we saw a few seine nets and many trap floats, but they were all located well out of the main channel.
The Chestertown Marina is a municipal marina located within easy walking distance to most of the attractions and dining in town. The city purchased the marina, rebuilt it, and maintains 15 transient slips to welcome visitors. Make slip reservations on their webpage by clicking on the Reservations tab. Or call (410) 778-3616 to speak with the manager, Paul Coleman. Paul or his assistant, Tom, should be there to greet you and help with docking. Be aware that there may be some river current flowing through the marina. The marina has both floating and fixed docks.
A Tall Ship in Chestertown!
Chestertown is home to the schooner Sultana. It is the flagship of the Sultana Education Foundation. The mission of the Foundation is to “provide transformative educational experiences in which students investigate the natural and human history of the Chesapeake Bay while exploring solutions for a more sustainable ecosystem.” The Sultana is a classroom, an ambassador, and a landmark all in one.
In the late 1990s, local leader, John Swain, advanced the idea of building a reproduction of the (American-built) Royal Navy schooner HMS Sultana. A not-for-profit group, Sultana Projects, Inc., was formed to fund the construction of the ship. The town rallied to build a temporary shipyard and the keel for the Sultana was laid in October 1998.
Over 3000 students participated in the community and educationally led effort, with a core group of volunteers logging over 150,000 hours of time building the ship. The Sultana was launched in March 2001. Since then, more than 8000 students a year have boarded the Class B Tall Ship for educational trips consistent with the Foundation’s mission. To learn more, visit sultanaeducation.org.
By Mike Pitchford, Steve Sharkey, and Brian Leney