Chestertown, a hidden gem on the Chesapeake Bay — 2 reasons to visit this summer

Historic town has gone all out to ensure the health and safety of its visitors as Maryland starts to reopen from its strict quarantine

Estimated reading 15 – *SBFL 10 – PLANNED and VISITED – Honestly, there is nothing hidden about historic Chestertown, Maryland.  As a matter of fact, it’s been well known from the Colonial Era, down to the 1940s as the home of the baseball superstar, Bill “Swish” Nicholson, and today, as the home port of Sultana and more. It’s only hidden if you are on the Chesapeake Bay headed down to enter the Intracoastal Waterway (ICW) in Norfolk, Virginia, — sailing in between Boston and Florida and not slowing down to smell the roses, so to speak.

As some boaters know, the ICW is a navigable, toll-free shipping route, extending for about 3,000 miles along the Atlantic Ocean and Gulf of Mexico coasts in the eastern and southern United States. Historically, it was envisioned to have a continuous channel connecting the many sounds, bays, lagoons, rivers, and canals from New York City, New York, to Brownsville, Texas.  Unfortunately, the link through northern Florida was never completed.  It is now two sections: Atlantic and Gulf.

1938 Map of ICW, Norfolk to North River

One of the great things about the waterway is that it’s federally maintained and, again, it is free. In some of my past blogs, I talked about some super-special people (see Pick your inspiration — 1902, 1958, 1960s, or 1999), who have done not just the Atlantic leg of the ICW, but the entire 6,000-mile journey around all legs of the ICW. If you are sailing from Boston down to the Florida Keys, before you reach ICW Mile Zero in Norfolk Virginia, you have two choices when you reach Delaware. You can either take the long, arduous outside route around Cape Charles, Virginia, or hop a ride on the fast-moving currents of the Chesapeake & Delaware Canal to the headwaters of the Chesapeake Bay, that will give you a much pleasanter journey down to Norfolk. That’s not to mention the gift of the ability to stop by some great towns and be a stone’s throw distance from Washington, DC, on the shores of the Potomac River.

A gem waiting for you on the Chester River 

On your way down to the South on the upper Chesapeake Bay, I want you to pay attention to the great Chester River on your port side (left, for those not familiar with boating lingo) before you reach the Chesapeake Bay Bridge.  That is the left turn most boaters transiting through the Bay to the ICW just do not realize they are missing and pass by.  This year, plan to make your turn and get into the Chester River and go up North a few miles.  Your reward will be not just reaching Chestertown, but also the pleasure of the entire journey along this scenic river. A unique countryside and the shores of the river will awe you.  That is reason #1. The pristine countryside will display all its beauty as if nature and humans somehow made a kind of peace, an unlikely alliance in the 21st century for a gentle balance with each other.

Two duck hunting blinds on the Chester River. (The one in the center is red in color, the other light brown one is back on the shore on the right). Photo by: L. Kazaz

You will notice duck hunting blinds on the shores of the river, displaying the longtime duck hunting heritage and culture of the region.  While winding through the beautiful geography, the river finally will lead you to its man-made gem, the historic colonial town of Chestertown, which started as a colonial port more than three centuries ago. The entire river journey and the historic town will be your reward for deciding to spend a couple of days there.  If you want to reach there by land, you may be surprised to know that Chestertown is in a prime location, less than 2 hours away from Philadelphia, Pennsylvania;  Baltimore, Maryland; Washington, DC; Alexandria, Virginia; and Rehoboth Beach, Delaware. That is not to mention Maryland’s great historical coastal towns along the Chesapeake Bay, such as Annapolis, the state capital,  as well as St. Michaels and Oxford.

From 1706 to the present day

Chestertown is one of the best-preserved colonial seaports in the United States. It was founded in 1706. It gained importance when it was named as one of the six Royal Ports of Entry of Maryland for the upper Eastern Shore.  In 1782, Washington College became the first college chartered after American independence from the British, under the patronage of President George Washington. Notable Washington College alumni include John Emory, for whom Emory University was named.

By 1790, the town was the geographical center of the population of the young United States. Bustling wharves lined the waterfront. Local crops were bound for Europe and the Caribbean. Its navigable river made the booming town rich. Finally, Chestertown was incorporated in 1805, and was named for the Chester River. Today, the population of the town is around 5,000 and the majority of today’s water traffic comes from recreational boating. There are a sizable number of buildings in town that are registered on the National Register of Historic Places in the United States, the federal government’s official list of districts, sites, buildings, structures, and objects deemed worthy of preservation for their historical significance.

Today, the wharves are gone and the shoreline is significantly different from earlier eras, especially since the new Chestertown Marina and 98Cannon, a great riverfront grill, were built. By the way, here is a tip if you want to see some satellite and land photos of the modern marina area. Those map sites are not caught up with the new marina grounds and still show the old pictures. The new marina that you’d be visiting is below.

Chestertown Marina. Photo courtesy of

This brand new, modern marina has all the creature comforts for all types of boats.  With its friendly marina management, it offers dockage with electric (100, 50 and 30 amp services), water connections for seasonal and transient boaters, diesel and gasoline services, waste pump out, some travel-lift capabilities, security and safety watch, access-controlled laundry and bathrooms, transient and trailer parking, plus more.

Chestertown marina manager Paul Coleman

Sometime after your arrival, and settling in your slip, make sure to stop over to see the Schooner Sultana on the docks. Sultana is the exact replica of the original 1768 schooner. When we stopped by to admire her beautiful craftsmanship, the crew was just finishing the process of bringing down her sails. Given the current coronavirus pandemic, the Sultana Education Foundation decided to close the schooner to the public because social distancing just isn’t possible in the close confines of the ship. However, the crew told us that they are continuing their educational programs for schools on Zoom. That said, even if you can’t go on board, taking a look at her close up is still a treat. 

Chatting with other boaters

While visiting, one of our favorite activities in a marina is to chat with other boaters. Upon arrival to Chestertown Marina, we bumped into two very energetic and cheerful couples, Todd and Lori, and Tom and Laura, waiting to get gasoline for their boat.  They were from Kent Island, on the other end of the river on the Chesapeake Bay.  They said they were taking advantage of the great day on the river. They were there to get gas, but after seeing the outdoor seats of 98 Cannon grill, they decided to eat there, too.  Sooner or later, the conversation ended up on how everyone was coping with the pandemic, of course.  Naturally it was on everyone’s mind.  They explained how they were impacted. 

Two very energetic and cheerful couples, Todd and Lori, and Tom and Laura

They said despite the challenges they have adapted.  In earlier days, when there were no masks to buy, they ordered bandanas for their teams, definitely respecting and supporting the Maryland state policy of everyone wearing masks in their workplaces. Admittedly, while we are cruising we do not wear masks.  They, too, were not wearing masks. They said that they are a close-knit couple and have been wearing masks when they are on land and near other people.

Jim and Linda Montague on their boat Rejoice

Later, we spotted Jim and Linda Montague on their boat Rejoice. They were transient boaters from St. Michaels, MD, visiting Chestertown for a few days. They say every summer they spend a lot of time in their boat visiting other towns.  They have done the Atlantic ICW trip 3 times and, to our delight, they shared the best spots and which were the best restaurants to eat at on the way to Florida. This year, they were quarantining on their boat and are spending several days in Chestertown

Visiting the historic district

This is reason #2. After seeing Sultana, you can walk to another part of the waterfront, which is also a part of the historic district.  Within walking distance to the Chestertown Marina is the Cannon Street Pier. If you have rented kayaks or brought your own, you could launch them from the  floating Cannon Street Pier, leading you to a great experience waiting for you on the Chester River Water Trail.  The water trail is a component of the Captain John Smith Chesapeake National Historic Trail, managed by the National Park Service. Two nearby water trails are Radecliff Creek and Morgan Creek.

Historic  Custom House

A large brick building near the Cannon Street Pier is the historic  Custom House. However, as we understand it, His Majesty’s Customs was likely in an adjacent building. The Custom House lets you explore the history of Chestertown. You will want to take the free audio tour, a lively presentation of the sights and sounds of life in Chestertown in Revolutionary times. Since you are now in the historic district of Chestertown, I recommend that you keep walking away from the waterfront. Within a few hundred yards, you will find yourself in the center of the historic district, Main Street Chestertown

Jim Montague, owner of Rejoice, expressly recommended us to visit the Evergrain Bread Company,  especially before noon.  He said, “Be there well before noon, otherwise most of the goodies will be gone.” We were there alright, but at the end of the day, right before the store closed and missed the most coveted freshly baked muffins, scones, french baguettes, and other wonderful bakery goods. However, we can attest that their brownies were delicious. 

Adapting for the next reality

I can almost hear some of my avid readers questioning the wisdom of not staying put in our home during the Covid-19 pandemic. However, let me reassure you that we have indeed been quarantined during the last 4 months. Chestertown is in Maryland, which is now in its Reopening Stage 2, which allows us to do some limited traveling there, as long as we wear masks and social distance.  As we all know, boating is one of the best social distancing activities that any one of us can enjoy. Also, we all are adapting for the next reality, so many smart waterfront coastal towns, such as Chestertown, are also adapting and are well- prepared for visitors and set for thriving during these trying times.  Starting with posted signs on the streets and establishment doors, the town clearly declares their intent of taking everyone’s health seriously.

A posted street sign on masks, Chestertown, MD

With its masks and additional procedures, it appears that the entire town is sticking to health protocols put in place to ensure the health and safety of visitors and customers.  Initially, we were planning to eat in our boat, Life’s AOK, and just walk around outside to see the historic buildings. The visible appearance of the town’s health safety measures and participation by all establishments and visitors made us a lot more comfortable. We ended up eating on the outside deck of 98Canon, facing the riverfront, as well as  visiting a couple of retail establishments, including Evergrain Bread Company. It was our first meal in a restaurant, albeit on an outside deck, since early March and it was marvelous. The food, the service, and the view were just wonderful. (We can heartily recommend the fish tacos!) 

Fish tacos of 98Cannon

If you go to the 98Cannon Restaurant,  you will need to make a reservation in advance. I suppose it is in order to manage the social distancing policies for everyone’s satisfaction. You will be greeted by friendly staff with masks and they expect you to have a mask in return, for the safety of all. All wait staff also wear face masks at all times.  The tables are spaced at least 6 feet apart. If you prefer outdoor seating as opposed to the air-conditioned indoors, you will find ample space looking at the grand Chester River.  

In the case of retail stores, such as Evergrain Bread Company, they only accept 5 customers with masks at a time to enter into the store, to assure proper social distancing, not to mention all of the staff are wearing masks.  I asked the bakery staff how they feel about working with masks. Their response was quick and frank. They were continuing to serve customers as usual, but with the new heightened health procedures in place due to the pandemic. That benefited everyone. 

Evergrain Bread Company, they only accept 5 customers with masks at a time to enter into the store

While we were inside Evergrain for only about 10 minutes, that was a welcome experience as well.  Chatting with the friendly staff, getting to check out what was left on their dessert shelves under their glass counter, and picking up some delicious chocolate brownies and homemade granola felt so good. 

Chester River Packet Company

Granted, you may have arrived in Chestertown on your boat, but there is also an opportunity to enjoy the Chester River and the waterfront of the historic town with a guided tour on the River Packet. Packet boats and ships were the backbone of water travel in the United States throughout the 18th century and well into the 19th century. Packets got their name from the boats used in Europe as far back as the 17th century to deliver mail (paquette) and to transport passengers. Packet ships (packet liners) did something which was novel at the time: they departed from port on a regular schedule.

Chester River Packet

This river excursion boat in Chestertown, a 65-foot River Packet, began her career as Seneca Chief on Seneca Lake in upstate New York. Later, she was moved to the Florida Keys and eventually South Carolina, where she was used for river tours in the Charleston area. Now located in Chestertown, the River Packet has been completely refurbished by local craftsmen.

Well, that’s it for now. Stay well. I hope to say hello to you if you spot my boat, Life’s AOK, in one of the locations that I’m hoping to visit in 2020, that is if Coronavirus permits us.

I bid you Fair Winds and Following Seas.

3 things I learned

  • Packet boats have an interesting history and a place in the American experience.
  • More on Chestertown today
  • Washington College in Chestertown is a great private liberal arts institution with a 10 to 1 student-teacher ratio. Today, it has a total undergraduate enrollment around 1,500. It is set in a rural 112 acres. Notable Washington College alumni include John Emory, for whom Emory University was named.

2 things I recommend

How easy?

Marina where you can tie up your boat

  • From its dockage with electric (100, 50 and 30 amp service) and water connections, access-controlled laundry and bathrooms, security and safety watch, the brand new five-star Chestertown Marina has everything a boat may need. 

*SBFL stands for Slow Boat to Florida. It is a series of my blog posts, which started with a posting that had the same title.  Each numbered heading has two parts. The first is “Planned,” and when we visit the planned location, a “Visited” label appears at the beginning, next to SBFL. The essence of this series is not to seek new lands and exotic cultures. Rather, it is to cover our journey of discovery (hence the title of our blog Trips Of Discovery) that has to do with seeing with a new eye the coastal locations of the Atlantic Intracoastal Waterway (ICW) where present-day America started to flourish. The SBFL series represents part travel, part current and historical anthropological highlights of selected locations and coastal life.  We’re comparing then and now, based on observations made by Dorothea and Stuart E. Jones in their 1958 National Geographic article titled, “Slow Boat to Florida” and a 1973 book published by National Geographic, titled America’s Inland Waterway (ICW) by Allan C. Fisher, Jr. We also take a brief look at the history of the locations that I am writing about. Finally, we bundle it up with our observations during our actual visits to the locations and our interviews with local residents. Think of it as a modest time capsule of past and present. My wife and I hope that you, too, can visit the locations that we cover, whether with your boat or by car. However, if that is not in your bucket list to do, enjoy reading our plans and actual visits as armchair travelers anyway. Also, we would love to hear from you on any current or past insights about the locations that I am visiting. Drop me a note, will you?

1 Response

  1. March 15, 2021

    […] We’ve had a few small day trips within the Maryland borders of the Chesapeake Bay, such as to Chestertown and Swan Creek. However, we’ve just been in planning mode for the rest of our Atlantic […]

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