The Eastern Shore’s Most Vibrant Tucked-Away Town
Why You’ll Want to Go
As one of Maryland’s oldest towns, Chestertown is a colonial gem that exudes charm on many levels. As one of the original trading posts of the Eastern Shore, Chestertown has a long history from the farmlands of the peninsula to the waters of the Chesapeake and beyond. Today, Chestertown’s sidewalks are lined with boutique shops and art spaces, bakeries and bookstores, to make your time there unique and memorable. The downtown’s close proximity to Washington College invites cultural events throughout the year; the Schooner Sultana leads the charge in bringing tall ships to the Downrigging Festival each November; and a lively farmers market on the weekends brings food and produce from all over the shore.
What You Can Expect to Find
Chestertown’s highlights are all accessible from the water, allowing visitors to experience the best of the town without having to depend on vehicular transportation. In this sense, Chestertown is a boater’s paradise. To walk from the dock to the town square might take eight minutes, but build in a few extra minutes to look in shop windows and maybe get some ice cream.
You’ll find many locals who were born and raised in town, often going back generations. Their love for this river town translates into a community that celebrates its history, and works hard to preserve it. Many of the shops along High Street hold original architecture, and most chain coffee shops or fast food sandwich places have managed to be kept out of the downtown area. Walking through the narrow city streets, you’ll find colonial-feeling cottages with gardens bursting over the tops of picket fences. Bring a camera.
Getting There
If you’re coming by boat, it’s about a 25-mile trip from Love Point Light on the northern tip of Kent Island to the Chestertown Marina dock. The river itself offers some of the most beautiful coves to spend the night, so we recommend splitting your trip into multiple days (especially if you’re traveling by sailboat).
Immediately inside the Chester, you’ll find Grays Inn Creek, Langford Creek, and the Corsica River. All three are beautiful and quiet, and will act as fantastic hidey-holes in the event of a storm. The mouth of Langford Creek is located 12 miles upriver from Love Point Light, and splits roughly two miles upstream into the East and West branches. For a quiet night, we recommend the East Branch, as its rolling farmlands and relatively undeveloped terrain lend toward a more peaceful stay. Regardless of where you are, Langford Creek has many excellent anchorages, many with sandy beaches for exploring.
Comegys Bight sits just northeast of Langford Creek and is significantly exposed to the south and southwest, but it is a convenient anchorage if you’re traveling later in the day and need a quick spot to stop. It is opposite Conquest Preserve, which offers a quiet respite for the night.
Where to Stay
The closer you get to Chestertown, the more marinas are available. If you need a quick stop for gas, there’s Kennersley Point Marina just past Wilmers on Southeast Creek. If you’re looking for facilities as close to Chestertown as possible there are two good options: Rolphs Wharf Marina and River Inn on the southeastern shore, and the Chestertown City Marina in town.
Rolphs Wharf Marina is perfect if you want a night of seclusion. With a ship’s store, pool, beach bar and a cute bed and breakfast, Rolphs has all the necessary amenities and a little more. The marina sits on five acres of land, making it a great place for animals to stretch their legs.
If you want to experience all that Chestertown has to offer without having to call an Uber, Chestertown Marina is the place to be. The town of Chestertown purchased the city marina in 2011 and spent eight years transitioning it into an inviting port away from home for boaters. With 15 transient slips up to 18 feet in depth, the Chestertown Marina is a new, beautiful space within walking distance of everything Chestertown has to offer. The ShoreRivers riverkeeper organization rents office space from the marina, and so the landscaping offers a beautiful natural habitat reminiscent of non-urban spaces.
At Wilmer Park next door, there is a playground that was added a couple of years ago with some great equipment for the little boaters.
A waterfront restaurant shares the property with the marina, but a fire in 2022 created enough damage to shut it down. The building has been bought, however, and we expect to have a new place for waterfront dining by summer 2025.
History buffs will want to take advantage of the White Swan Tavern, a colonial-era inn located on High Street just a few blocks from the marina. Rooms have maintained the feeling of a Revolutionary War era, with low ceilings and tight door frames, but the amenities are all modern: lush bedding, romantic lighting, and delicious breakfasts full of local treats are all enjoyed, and a back garden and game parlors offer great places to read the newspaper while you finish a cup of coffee. There are only six guestrooms, however, so book ahead. And if you need transportation from the Marina, give them a call and ask about their golf cart.
What to Do
Have Fun with History. Chestertown itself has a colonial history that predates the Revolutionary War. Walking through town, you’ll find commemorative plaques with interesting information. If you’re traveling in the area around Memorial Day weekend, you can catch the Chestertown Tea Party, a festival celebrating the day in 1774 that locals held their own “tea party” akin to Boston’s , dumping the cargo of the brigantine Geddes, freshly arrived from England, into the water to protest the tea tax. If you’re bringing your boat up the river, there are other places to check out.
At the mouth of the Chester, the Eastern Neck National Wildlife Refuge is the site of many Native American artifact discoveries dating back almost 3,000 years. And traveling up the east fork of Langford Creek will bring you to Caulk’s Field, a War of 1812 battlefield in which the American militia beat a small British army, contributing to the fall of the British campaign against Baltimore.
Find a fun event on Washington College’s campus. As one of the area’s premier liberal arts colleges, Washington College makes it possible to see a play or musical, listen to a concert, or hear a famous writer read from their latest work while you’re ashore. Many of these events are free or low-cost, too; just check the calendar of events ahead of time.
Check out the Sultana. She’s hard to miss: a reproduction of a Boston-built merchant ship used by the British Royal Navy, the Sultana is used as a floating educational platform, taking visitors around the Chesapeake Bay to learn more about the environment. If you can’t swing a ride on her, the Sultana Educational Foundation offers fascinating public kayak paddles to explore the John Smith Trail.
Where to Eat
There’s good food in Chestertown. A staff favorite at CBM, Modern Stone Age Kitchen (MSAK) is one part bakery, one part gastropub. And its name isn’t just for show: it’s actually run by a food anthropologist. We love ordering a sandwich full of mozzarella and local tomatoes on homemade focaccia, but if the smoked chicken sandwich is on the menu, you must order it, no questions asked. MSAK also offers cooking classes throughout the year, allowing you to learn how to make your own sourdough if Chestertown isn’t an everyday drive for you.
If you need a simple sandwich and a quick coffee, Play It Again Sam is a great place to get a unique shot of caffeine and a bite from some of the nicest people on the Eastern Shore. Everything is simple with a twist: the roast beef sandwich comes with brie, and the classic BLT has a thick smear of avocado alongside layers of turkey and Swiss. With an iced coffee to go, we took our sandwiches to the park across the street and let the kids run while we got our energy back.
It’s a local secret, but a green light outside the Play It Again Sam door is the telltale sign for Zelda’s Speak Easy, a hidden gem of a space that serves craft cocktails when it feels like it. You can tell when Zelda’s is on by the green light at 108 Cross Street: if it’s on, there’s a bartender hiding somewhere. If the light is out, you’re out of luck.
If you’re looking for something upscale, we recommend The Kitchen at The Imperial, where Chef Steve Quigg works with local farmers to put out a menu indicative of a much bigger city. Recently we tried the “Chesapeake Channa” served over local produce and a Riesling beurre blanc, and were stunned when we realized we were eating snakehead.
If you need a simple sandwich and a quick coffee, Play It Again Sam is a great place to get a unique shot of caffeine and a bite from some of the nicest people on the Eastern Shore. Everything is simple with a twist: the roast beef sandwich comes with brie, and the classic BLT has a thick smear of avocado alongside layers of turkey and Swiss. With an iced coffee to go, we took our sandwiches to the park across the street and let the kids run while we got our energy back.
It’s a local secret, but a green light outside the Play It Again Sam door is the telltale sign for Zelda’s Speak Easy, a hidden gem of a space that serves craft cocktails when it feels like it. You can tell when Zelda’s is on by the green light at 108 Cross Street: if it’s on, there’s a bartender hiding somewhere. If the light is out, you’re out of luck.
Shopping
Chestertown shopkeepers appreciate boating traffic, and as such many of their goods and wares reflect the boater’s sensitivity.
There are plenty of shops on High Street to find something fun to take home with you. Bee Crafty Antiques and Collectibles offers unique gifts, and most are from local artists. Their kitchen selection offers cooking utensils, pots, and pans that are specialized for boating. The shopkeepers act as unauthorized guides for the best restaurants, too.
On Cross Street, Chester River Wine and Cheese has a great selection of (surprise!) wine and cheese for your next happy hour. If you need to entertain and don’t feel like cooking, personalized charcuterie boards are available at reasonable prices.
The Eastern Shore has some of Maryland’s best bookstores, and The Book Plate is one of the absolute best. There are multiple rooms chock full of used and new books from every genre, and a robust section on local history in particular made us very happy. Need help choosing a good book to get lost in on the long sail home? Ask for assistance from the staff: they know all the best titles.
