The Best Small Town In Maryland For A 3-Day Weekend
With nearly 17,000 miles of rivers and the Chesapeake Bay at its edge, a long weekend trip in Maryland has never felt more tempting. In fact, the hard part of planning a getaway here is often simply deciding which town in Maryland to visit! Chestertown might be the easiest way to experience Maryland all at once. This town, positioned along the banks of the Chester River, has roots dating back to 1706. Its waterfront parks and preserves are the perfect place to relax and connect with nature for a while, too. Looking for a weekend that feels quintessentially Maryland? Chestertown is it.
Chestertown’s Downtown District
With all of its coffee shops, bakeries, galleries, and restaurants, you will definitely want to dedicate a day to exploring Chestertown’s downtown district. If you arrive in town in the morning, consider starting your adventure at Evergrain Bread Company, a local bakery that was founded in 2010 and is renowned for its delicious artisan breads, pastries, and cakes. You’ll also find a variety of beverages on the menu, including espresso, specialty lattes, and teas, if you need a little caffeine boost.
Once you are fueled up for the day, you can spend a few hours browsing some of the local shops and art galleries. Local nonprofit Chestertown RiverArts runs an art store that sells all kinds of locally made artisan products, including ceramics, paintings, jewelry, and cards. Make sure to stop by Twigs & Teacups, a beloved boutique on South Cross Street that sells kitchenware, apparel, and toys, among other items that would make great holiday gifts. Once your appetite starts to kick in, stop by Watershed Alley for lunch or dinner, which prioritizes the use of locally sourced Chesapeake ingredients, serving seafood, steak, burgers, and more.
Historic Landmarks & Museums
Since its founding in 1706, Chestertown has been a pillar of Kent County’s government and a longtime college town. Thus, exploring the colonial-era historic district and the college is a must during your visit. Washington College, established in 1782 and recognized as the oldest college chartered in the sovereign United States, is a great place to start. On South Water Street, meanwhile, visitors can view landmarks like the Hynson-Ringgold House, an 18th-century Greek Revival residence with Flemish bond brickwork that now serves as the official home of the college’s president.
If the town’s history has piqued your interest, you’ll love visiting the Historical Society of Kent County, which has an on-site museum and research library. Until the end of 2025, the museum is hosting the rotating exhibit, On New Shores: A History of Jewish Lives in Kent County, which explores the lives of Jewish immigrants in the county who arrived in the early 1900s. The museum is currently open on Thursdays through Saturdays, late morning to early afternoon.
Nature Preserves and Parks
If you are looking to get a bit of exercise during your weekend away, you’ll find some great green spaces in the area. The Lawrence Wetlands Preserve is right on the edge of the historic district, featuring 8.5 acres of upland forest, marsh, swamp, meadows, shrublands, and a freshwater pond. There are several paths and a boardwalk you can use to explore these ecosystems. Keep your eye out for turtles and seasonal waterfowl, and raptors during your visit! The preserve is open daily from dawn to dusk, except when it is in use for educational programs.
Wilmer Park is right down the road from Lawrence Wetlands and is a great place to enjoy the Chester River. This waterfront park has all kinds of amenities, including a kayak launch site, a new playground, a modern art sculpture, a pavilion, benches, a gazebo, walkways, and an open area that holds concerts and festivals throughout the year.
Historic Inns
With history dating back to the 1700s, it feels fitting that many of the town’s inns offer historic experiences as well. The White Swan Tavern, for example, has been a well-known landmark since the pre-Revolutionary War era. In the 18th century, it was described as “a comfortable… Public House,” and today, it continues the tradition with six guest rooms and a rotating hot breakfast served each morning. Here, you’ll also be centrally situated on High Street, allowing you to easily access local restaurants and shops around you!
Brampton 1860 is another one of the most popular inns in town. Sitting on 35 acres of gardens and meadows, this property is located slightly west of town, allowing you to disconnect in Maryland’s countryside. The inn itself is incredibly historic as well, housed in the 1860 Manor House that is now listed on the National Registry of Historic Places.
Although Chestertown is home to only a little over 5,000 residents, it is filled with an impressive variety of activities and landmarks. Are you interested in history? The town is filled with colonial homes and inns to appreciate. Prefer a weekend out in nature? Wetlands and waterfront parks await. All you have to do is pick your travel dates and get ready to have one of the best three-day weekends yet!
