Kent County, Maryland, packs a surprising amount into a small corner of the Eastern Shore. You can walk past 18th-century homes in Chestertown, spend an afternoon along the working waterfront in Rock Hall, swim at Betterton Beach, or head out on the Chester River. Between the towns are miles of farmland, quiet back roads, and creeks leading toward the Chesapeake Bay.
For first-time visitors, knowing where to start can be the hardest part. Kent County has five incorporated towns and more than 200 miles of shoreline, and each area offers something different. This guide covers the places worth visiting, what to do while you’re here, and how much time to set aside for your first trip.
Where Kent County Is, and How to Get Here
Kent County sits on Maryland’s Upper Eastern Shore, bordered by the Chesapeake Bay to the west, Delaware to the east, and the Sassafras and Chester Rivers marking its northern and southern edges. It’s within driving distance of Washington, D.C., Baltimore, Philadelphia, Annapolis, and Northern Virginia, making it a practical choice for a weekend getaway from several Mid-Atlantic cities.
Visitors reach the county by a mix of major highways and smaller state roads, with MD-213 and MD-20 among the routes you’ll use most once you’re in the area. No passenger rail service runs directly into Kent County, so a car is the most practical way to explore the towns, waterfront areas, and rural parts of the county.
A Little History
Kent County was established in 1642, making it one of Maryland’s oldest counties. It saw significant activity during the War of 1812, including British raids along the Sassafras River and the Battle of Caulk’s Field. That history is still visible today at places like the Kitty Knight House in Georgetown and the battlefield site.
Washington College, founded in Chestertown in 1782, is Maryland’s oldest college and one of the oldest in the country. Together with the county’s long colonial and maritime history, this has helped preserve a substantial collection of 18th- and 19th-century buildings and historic districts.
For the full story of the county seat, our guide to the Chestertown Historic District goes block by block.
The Five Towns of Kent County
Kent County has five incorporated towns, and they’re not interchangeable. Knowing the difference before you go will save you from driving somewhere expecting one thing and finding another.
Chestertown is the county seat and the largest town, home to Washington College, a walkable historic waterfront district, and the county’s best concentration of shops, restaurants, and galleries. If you only have time for one town, this is usually it. Our complete guide to things to do in Chestertown covers everything.
Rock Hall is the county’s working waterman’s town, smaller and quieter than Chestertown, with marinas, seafood restaurants, and direct water access that make it a natural base for anyone who wants to be near a dock rather than downtown. See our guide to Rock Hall, MDÂ for the details.
Betterton is a small former Chesapeake Bay resort town with a sand beach, something not every Eastern Shore town can claim. It’s one of the most-visited spots, and for good reason. Our guide to Betterton Beach covers what to expect.
Galena sits inland near the Delaware line and has a small-town Main Street with local shops, including antique shopping. It’s an easy add-on if you’re already headed toward Chestertown from the north.
Millington is one of the county’s smaller, more rural towns, located along the Chester River. It’s not a primary destination for most visitors, but it reflects the county’s working agricultural landscape.
What Kent County Is Actually Known For
Beyond the towns themselves, a few things define a visit here:
The water. With more than 200 miles of shoreline and direct access to both the Chester and Sassafras Rivers, Kent County is built around boating, kayaking, sailing, and fishing. Eastern Neck National Wildlife Refuge, at the confluence of the Chester River and Chesapeake Bay south of Rock Hall, adds serious birdwatching to that list.
The history. Beyond Chestertown’s historic district, the county includes numerous historic properties, districts, and sites that reflect its colonial, maritime, and agricultural past.
The food. Agriculture and the Chesapeake’s fishing and seafood traditions remain an important part of the county’s identity, and that shows up on local menus and at farmers’ markets. Chesapeake Bay blue crab, local produce, and a small but serious wine and craft beverage scene are all part of the draw.
Less rush. This rural county is designed to feel more relaxing than many larger Chesapeake destinations. It’s for people who wish to slow down and rest.
How Much Time to Plan
A single day is enough to get a real feel for Chestertown alone. A full weekend lets you split time between Chestertown and Rock Hall, with a stop in Betterton. If you want to add Galena’s shops or explore the water, three to four days gives you room to explore without rushing.
Spring and fall are appealing for mild-weather sightseeing, while summer brings more activity to waterfront destinations such as Betterton and Rock Hall. If you’re visiting during the warmer months, book your stay in advance.
Where to Stay in Kent County
Make Inn at Huntingfield Creek your home base for exploring Kent County. Set on 70 acres near Rock Hall, the inn puts you within a short drive of Chestertown while giving you plenty of reasons to spend time right on the property. Choose from individually decorated guest rooms in the Main House or private cottages, and start the morning with a full country breakfast before heading out for the day.
There is plenty to come back for, too. Spend an afternoon by the saltwater pool, explore the grounds, or take advantage of the complimentary kayaks and bikes. If you’re searching for the best Bed and Breakfast in Maryland, Inn at Huntingfield Creek gives you a comfortable place to settle in while keeping Rock Hall, Chestertown, and the rest of Kent County within easy reach.
Book your stay and give yourself a few days to explore Maryland’s Eastern Shore.
Frequently Asked Questions
What are some fun things to do in Kent County, Maryland?
Walk the historic district in Chestertown, spend an afternoon on the water kayaking or sailing the Chester River, visit Betterton Beach, browse the shops in Galena, or catch the Saturday farmers market in Chestertown. Most visitors build a weekend around two or three of these rather than trying to do everything in one trip.
What towns are in Kent County, Maryland?
Five incorporated towns: Chestertown, the county seat, Rock Hall, Betterton, Galena, and Millington.
How far is Kent County from Washington, D.C., Baltimore, and Philadelphia?
Kent County is within driving distance of Washington, D.C., Baltimore, Philadelphia, and Annapolis, making it a practical Eastern Shore weekend destination. Drive times vary depending on where you’re starting and whether you’re headed to Chestertown, Rock Hall, Betterton, or elsewhere in the county.
What is Kent County, Maryland known for?
Its well-preserved colonial and Federal-era architecture, its working waterfront towns, direct access to the Chesapeake Bay and Chester River, and longstanding agricultural, boating, fishing, and seafood traditions.
Where should I stay in Kent County, Maryland?
Inn at Huntingfield Creek sits near Rock Hall and a short drive from Chestertown, making it a great base if you want to explore more than one town during your visit.
