Cruising the Chester and Visiting Chestertown by Sailboat or Land

Local Tips on Sailing Anchorages on the Chester and What To Do for Sailors in Chestertown

"One of the reasons why the Chester is so great is that it’s off the beaten path,” says Drew McMullen, the president and founder of the Sultana Education Foundation. “You have to work a little extra hard to get to Chestertown. It has the same population now as it did in 1776; that’s why it’s so well preserved.”

McMullen, who’s lived in Chestertown since 1995, notes that on the Schooner Sultana, traveling at six knots, the crew can go from the entrance of the winding Chester River to the colonial seaport in about four hours “depending on the tides.”

Sultana sails chestertown
The Schooner Sultana sails along the Chestertown waterfront on the Chester River off the Chesapeake Bay in Maryland. Photo by Chris Cerino

We reached out to McMullen and Annie Richards, the Chester Riverkeeper, to learn more about their connection to the river and what anchorages and shoreside attractions they recommend to cruising sailors.

Richards grew up a mile north of the Chester River Bridge and admits that she took all the sailing, waterskiing, and watery fun for granted until high school when she had “a transformational experience at the Echo Hill Outdoor School.” She spent a week on the Skipjack Elsworth “exploring marshes and hearing poetry and stories of those whose lives had been shaped by the waterfront. I started to understand what a unique resource it was.”

Richards later worked at the school, earned her captain’s license at the age of 20, and left for a few years to “get some bluewater experience.” After a few years of marine-related jobs, such as working on a charter catamaran, for Seamester in southeast Asia, and for Maine Maritime Academy, she returned to the Chester to settle in and raise her family with her husband Forrest Richards, the senior captain of the Sultana. She’s been the Chester Riverkeeper for three years and goes out on the river every week for seven months of the year for water-quality monitoring, as well as sailing with family out of the Rock Hall Yacht Club.

“There’s value knowing a place your whole life,” says Richards about what makes the river special. “When you look out on the water, there are miles of shoreline that haven’t changed for hundreds of years (except for phragmites!). At every cliff, every cove, I have some memories from childhood, sailing, work, or taking my kids there (two boys, five and one). I feel as if heading down the Chester River is like opening up a scrapbook.” 

Where To Anchor

Both of the Chestertown locals we interviewed grew up sailing. McMullen, who cut his teeth on a Sunfish, later owned a Cal 25 and “sailed all over the Bay.”

When asked what anchorages he’d recommend to cruising sailors visiting the Chester, he says, “Work your way up. Queenstown Creek is great. Up creek to left, there’s a beautiful anchorage. As with most anchorages on the Chester, you’re not going anywhere except at anchor.”

chester riverkeeper boating
Annie Richards, the Chester Riverkeeper of ShoreRivers, grew up on the Chester River and now spends a great deal of time boating recreationally as well as for work.

Richards notes, “Go to Reed Creek on the Queen Anne’s side, just before the Corsica River. If you’re a diehard fisherman, anchor there. You will find incredible solitude, beautiful views of 1000-acre farms, and little tributaries you can dinghy up and explore.” 

As for the Corsica River, McMullen says, “There’s a little bay. If you go up and around to the next little bay, that one is spectacular. It’s well-protected. You could go up in a hurricane.”

Across the Chester from the Corsica, McMullen recommends “Grays Inn Creek, the first left going upriver.”

He also enjoys Langford Creek, the east and west forks. “Go up past where they split; they’re both beautiful with pretty houses. I personally like the east fork of Langford Creek. That’s where we took Sultana as a hurricane hole (we don’t do that anymore, as we made our own hurricane dock).”

Richards says her favorite is Langford Creek “hands down. If you’re not going there, you‘re missing the jewel of the river. In summertime the west fork has good holding in storms. You can dinghy into Cacaway Island for lunch.”

A little farther north sailors will find Comegys Bight. McMullen says, “It’s a very good anchorage, a little exposed, but unless it’s howling, you’re fine.” He notes that there can be a lot of powerboats in summer, yet “in waterfowl season, it’s full of birds. Go in October!”

More Tips for Sailors

When asked what sailors should know about these days, McMullen responds, “Chestertown has a new marina (Chestertown Marina). It’s a humongous improvement. It’s beautiful with floating docks and nice bathrooms and showers; a great place for a group of boats to come.”

downrigging sailboats chestertown tall ships
Tall ships at Chestertown for Sultana's annual Downrigging Weekend. Photo by Eric Moseson

For visiting cruisers, “There’s plenty to do within walking distance—there’s a food store downtown that is a very nice place for cruisers to go (Chestertown Natural Foods, 303 Cannon Street). There’s good shopping, too. There’s plenty to do to kill a day or weekend in Chestertown.”

Richards says, “As a recreational boater on the Chester—I swim and fish, and my children and dog do, too—I know how to regularly access the bacteria score. After significant rain events, check in with ShoreRivers about the pollution loads. ShoreRivers regularly monitors for bacteria from Memorial Day through Labor Day. We test on Thursdays, so we’re ready for the weekend. All the data are available on our website: Also, I recommend the Swim Guide app for any public access location anywhere in the world.”

Richards also hopes sailors learn where the subaquatic vegetation grows (find Virginia Institute of Marine Science (VIMS) interactive SAV map). “If you’re going into an anchorage where there is a thriving SAV bed, maybe anchor a little bit deeper to avoid messing up grasses. Trim your dinghy motor to not impact grasses.”

An aerial of Chestertown, Maryland. Photo courtesy of Kent County Maryland

Local Favorites

McMullen and Richards’s local tips for food and beverage within walking distance of the waterfront:

  • Casa Carmen Wines and Bodega. Regional wines and tapas, “simple menu and fun (312 Cannon Street).” 
  • Evergrain Bakery Company: “An old-world-style bakery offering European bread and pastries, baguettes, croissants, and pre-made sandwiches to go that you can take back to your boat (201 High Street).”
  • The Kitchen at the Imperial: More traditional Eastern Shore fare: crab cakes, steak, and farm-to-table menu (208 High Street).
  • The Retriever Bar: As the sign suggests, “Come, sit, stay.” Oyster bar, bistro menu, and cocktails (337 ½ High Street).
  • Watershed Alley Restaurant: “The rich tradition of the Chesapeake Bay watershed, updated, refined, and celebrated. Brunch, lunch, happy hour, dinner (337 High Street).”
  • Zelda’s Speakeasy: No sign, but there’s a green light on the door when it’s open on Thursdays and Fridays; second floor. Limited food, fun for a drink (108 S. Cross Street). 

Learn More

Sultana Education Foundation: Hands-on educational programs, camps, paddling, Annual Gala (May 11), and Downrigging Weekend (November 1-3);

ShoreRivers: Protects and restores Eastern Shore waterways through science-based advocacy, restoration, and education;

Explore Chestertown: Learn about the Chestertown Tea Party (May 24) and upcoming events, such as farmer’s and artisan’s markets;