Chestertown sits on the Chester River about twenty minutes from our front door, and with so many things to do in Chestertown, MD, it’s the perfect day trip. Founded in 1706 as an important colonial port of entry, it’s held onto its brick sidewalks and Georgian architecture in a way that few Chesapeake towns have, while also filling in the gaps with good coffee, a farmers market, and a small liberal arts college.
If you’re staying with us at Inn at Huntingfield Creek, Chestertown is one of the easiest and one of the most fun day trips on the Eastern Shore. Here’s how to spend your time there, whether you’ve got a couple of hours or a full afternoon.
Start With the Historic District
One of our favorite things to do in Chetertown, MD, and one of the best ways to understand the town is to walk it. The Chestertown Historic District covers several blocks of Water, High, and Church Streets, where sea captains and merchants built their homes in the 1700s and 1800s, many of which still survive today. Grab a self-guided walking map from the Kent County visitor center at 122 N. Cross Street (or download one ahead of time), and plan on an hour or so of unhurried wandering.
A few landmarks to visit on your walk:
- The Custom House, at the foot of High Street near the public dock, dates to 1746. Originally built as the residence and store of merchant Thomas Ringgold, the building now houses Washington College’s Starr Center for the Study of the American Experience.
- Washington College, founded in 1782 with George Washington’s permission to use his name and financial support, sits a few blocks from downtown and is worth a short detour if you like campus architecture or just want a quiet place to stretch your legs.
- Fountain Park and Wilmer Park both sit near downtown and make good spots to sit for a few minutes with a coffee.
For the deeper history, including the Tea Party connection and specific house-by-house detail, our companion guide to the Chestertown Historic District goes block by block.
Browse Downtown Shops and Galleries
High Street, Cross Street, and Cannon Street form the compact core of downtown shopping, and almost everything is locally owned. It’s a good stretch for browsing without an agenda:
- MassoniArt on South Cross Street, formerly known as the Carla Massoni Gallery, has anchored the local arts scene for decades, with rotating shows from regional and national artists.
- Chestertown Cooking Company stocks serious kitchen gear for anyone who wants to bring a bit of the Eastern Shore’s food culture home.
- Chester River Wine & Cheese Co. and Casa Carmen Wines both make good stops if you’re building a picnic or just want a glass of something local before dinner.
- Bad Alfred’s Distillery is a brewpub and distillery a short walk from downtown, with house-made spirits, craft beer, cocktails, and wood-fired pizza.
If it’s the first Friday of the month, time your visit for First Friday, when downtown galleries and shops stay open late, typically from 5 to 8 p.m., for an informal art walk.
Visit the Farmers Market
The Chestertown Farmers’ and Artisans’ Market runs year-round every Saturday morning from 8 a.m. to noon, rain or shine, along the 200 and 300 blocks of High Street and Memorial Row in the heart of downtown. It’s a working market, featuring produce, bread, plants, honey, and homemade goods from Kent County growers and makers. If your visit lines up with a Saturday, build your morning around it. Everything else downtown opens shortly after.
See the Sultana and the Chester River
Chestertown’s identity is tied to the water as much as to its brick sidewalks. The Schooner Sultana, a hand-built reproduction of a 1768 topsail schooner, is based here through the Sultana Education Foundation, which runs public sails and educational programs on the Chester River throughout the season. Watching the ship come and go from the town dock, even without booking a sail, is great for timing your walk around.
For a longer visit on the water, our guide to kayaking and paddling near the Inn covers put-ins along the Chester and Sassafras Rivers within easy reach of both Chestertown and Rock Hall.
Catch a Show or Explore the Arts Scene
One of the more unique things to do in Chestertown, MD, is to explore the local art scene. Chestertown is an amazing place when it comes to arts programming, largely thanks to Washington College’s presence:
- The Garfield Center for the Arts at the Prince Theatre hosts community theater, concerts, and film year-round in a restored downtown venue.
- Chestertown RiverArts runs a gallery and studio space downtown with regular exhibitions from local and regional artists. Learn more at our guide to Chestertown RiverArts.
- The Historical Society of Kent County, housed in the Bordley History Center, is a small but genuinely interesting stop for anyone curious about the region’s 300-plus years of history, with a smartphone-accessible walking tour of the historic district.
Eat and Drink Downtown
Chestertown’s dining scene is small but well above what you’d expect from a town this size, largely because it’s feeding both longtime locals and a rotating population of Washington College families and visiting boaters. Expect everything from an upscale tasting menu to a proper diner breakfast, often within a two-block radius. For the full rundown, see our dedicated Chestertown restaurant guide.
Time Your Visit Around an Event
A few Chestertown events are worth planning a whole trip around:
- Chestertown Tea Party Festival, held Memorial Day weekend, commemorates Chestertown’s 1774 resistance to British tea policies and reenacts the local story of residents throwing tea into the Chester River, with a parade, colonial encampments, and a full weekend of downtown programming.
- Downrigging Weekend, held each fall around Halloween, brings tall ships from up and down the East Coast into the Chestertown Marina for public sails and dockside tours. It’s one of the best reasons to visit in late October.
- Music in the Park, a free summer concert series, runs through the warmer months in one of downtown’s parks.
If you’re planning around foliage season specifically, our Maryland fall foliage guide covers timing for the whole region, Chestertown included.
How Much Time to Set Aside
Chestertown deserves a visit whether you have a couple hours or a full day. Here are some ideas of things to do in Chestertown, MD, depending on how much time you have:
- Two to three hours is enough for a walk through the historic district, a stop at a gallery or two, and a coffee.
- Half a day lets you add the farmers market (Saturdays only), a nice lunch, and time on the waterfront watching the Sultana.
- A full day works well if you’re also visiting nearby Betterton Beach or timing your visit around a festival weekend.
Chestertown is about a twenty-minute drive from Inn at Huntingfield Creek, which makes it easy to treat as a half-day outing without eating into the rest of your stay. Spend the morning on our property before venturing to explore the town and you’ve got a full day on the Eastern Shore without much driving at all.
Where to Stay Near Chestertown, MD
After exploring Chestertown, return to the quiet Eastern Shore setting of Inn at Huntingfield Creek, our Bed and Breakfast in Rock Hall, MD, just a short drive away. Set on 70 acres, the inn offers individually decorated guest rooms and private cottages, plus a full country breakfast featuring seasonal fruit, farm-fresh eggs, breakfast meats, and a rotating sweet dish.
There is plenty to enjoy at the inn between exploring things to do in Chestertown, MD, too. Guests can relax by the saltwater pool, explore the grounds, or borrow complimentary bikes and kayaks for a little more time outdoors. Back at the Main House, complimentary wine, beer, soft drinks, and homemade chocolate chip cookies are available in the library. With both Chestertown and Rock Hall close by, our Bed and Breakfast makes a convenient home base for exploring Kent County.
Planning a Longer Stay in Kent County
Chestertown is one of three towns to add to a Kent County itinerary, alongside Rock Hall and Betterton. If this is your first visit to the area, our first-timer’s guide to Kent County, Maryland is a good place to start before you map out which towns to prioritize. And if Rock Hall’s own waterfront and dining scene weren’t already on your list, our guide to Rock Hall rounds out the rest of the county.
Frequently Asked Questions
Is Chestertown, MD worth visiting?
Yes. It’s a historic colonial waterfront town on Maryland’s Eastern Shore, with a walkable historic district, a working farmers market, a small but strong arts scene, and river access.
Is Chestertown, MD walkable?
Very. The historic district, downtown shops, restaurants, and the town dock all sit within a few blocks of each other, so a car isn’t necessary once you’ve parked downtown.
What is Chestertown, MD known for?
Chestertown is known for its colonial-era architecture and Georgian homes along the Chester River, its history as an important colonial port of entry, the Schooner Sultana, and Washington College, which was founded in 1782.
How far is Chestertown, MD from Rock Hall, MD?
About 14 miles via MD-20, roughly 20 to 25 minutes by car. It’s an easy pairing for a single-day trip.
What is the best time of year to visit Chestertown, MD?
Spring and fall both work well, spring for milder weather and fall for foliage and Downrigging Weekend. The farmers market operates year-round. For a full seasonal breakdown, see our guide to the best time to visit Maryland’s Eastern Shore.
Where should I stay when visiting Chestertown, MD?
Chestertown has a few small inns, but many visitors stay in nearby Rock Hall, about 20 minutes away, for easier water access and a quieter setting. Inn at Huntingfield Creek sits between the two towns on 70 acres, with complimentary kayaks and bikes for exploring the water on the days you’re not in town.
Ready to make Chestertown part of your Eastern Shore weekend? Book your stay at Inn at Huntingfield Creek and you’ll have both Chestertown and Rock Hall within a short drive, plus 70 acres, a saltwater pool, and complimentary kayaks and bikes waiting when you get back.
