6 Undiscovered Small Towns In Maryland
Soaked in history and bursting at the seams with natural beauty, Maryland has much more to offer curious travelers than just its well-known cities of Baltimore and Annapolis. Sure, while these urban centers attract the majority of tourists, Maryland is also home to numerous small towns that remain largely undiscovered by the masses, which is a shame, as these quaint towns are not only rich in history and culture but also boast stunning natural landscapes. In fact, Maryland’s so pretty a place and has so many interesting things to see despite its relatively small size (it’s the ninth smallest state!) that it has been dubbed “Little America.”
And there’s no better way to experience a small slice of Americana than with a visit to one of Maryland’s lesser-known small towns. Not only do they demonstrate the state's colonial history and maritime traditions, but many of these towns are also located close to significant geographic landmarks such as the Chesapeake Bay, the Appalachian Mountains, and the Potomac River, offering a unique mix of scenic beauty and historical depth. Whether you're interested in exploring historic sites, enjoying outdoor activities, or simply strolling through quaint downtown areas, these six undiscovered small towns in Maryland present unique opportunities for visitors seeking a quieter yet extremely enriching travel experience.
Chestertown
Located on the Eastern Shore of Maryland along the banks of the Chester River, Chestertown is certainly rich in colonial history. Founded in 1706, it quickly became an important port town for trade with England, with many of its original historic buildings preserved and providing a glimpse into the town's storied past. Chestertown was also the site of its own "Tea Party" in 1774, just a few months after similar events in Boston, which had fomented early resistance to British rule. Visit today, and you can even participate in fun reenactments of this event at the Chestertown Tea Party Festival, which celebrates the town's revolutionary history each May.
These days, the town's waterfront and its park are a pretty spot for a picnic or a leisurely stroll, while those wanting to get out onto the water can rent a canoe or kayak (or bring one of their own). For the ultimate on-water experience, the Sultana Education Foundation offers cruises on a replica 18th-century schooner. Other local attractions include historic Washington College, founded in 1782, and one of the oldest colleges in the United States. Visitors can explore the college's stunning campus and the nearby historic district, which features many beautifully preserved 18th-century homes.
St. Michaels
St. Michaels is located on Maryland's Eastern Shore along the Miles River and is worth visiting for its fascinating maritime heritage. Founded in the mid-1600s, this attractive yet underrated community was once a center for shipbuilding and fishing with its nautical past still very much on display. A great way to learn more about this aspect of the town’s history is to pay a visit to the Chesapeake Bay Maritime Museum. Covering 18 acres of waterfront, this must-see attraction features an impressive collection of historic boats, exhibits on the region's maritime history, as well as a working boatyard.
The Hooper Strait Lighthouse, a preserved screw-pile lighthouse built over the water, is another maritime highlight and provides an insight into the life of a 19th-century lighthouse keeper. And for those wanting to enjoy some of the best views in Maryland, St. Michaels is situated on a peninsula that offers incredible views of the Miles River and the Chesapeake Bay.
Havre de Grace
Havre de Grace, located at the confluence of the Susquehanna River and the Chesapeake Bay, is an easy 50-minute drive northeast of Baltimore, making it one of the most accessible of the towns on this list… and perfect for a day trip or weekend getaway. Founded in the late 18th century, Havre de Grace was nearly chosen as the capital of the United States, losing out to Washington, D.C., by a single vote in 1789. The town also played a significant role during the War of 1812 when British forces attacked and burned much of it down, an event still commemorated today with re-enactments and displays.
Still an important port, the town's location at the head of the Chesapeake Bay provides stunning waterfront views and countless opportunities for boating, fishing, and birdwatching, especially at the nearby Susquehanna State Park. Havre de Grace is also home to several historical attractions, including the Concord Point Lighthouse, one of the oldest continuously operating lighthouses on the East Coast. The Havre de Grace Maritime Museum and the Lock House Museum, located in a restored canal lock house, offer further insights into the town's rich maritime and industrial history.
Ellicott City
One of Maryland's oldest and most historic towns, Ellicott City, was founded in 1772 by the Ellicott brothers and quickly became a center for milling and commerce thanks to its strategic location along the Patapsco River. It’s perhaps best known for its well-preserved historic district. Dubbed Old Elliott City and covering 325 acres, the oldest buildings here date from 1772 and are a delight to explore. Highlights include the B&O Railroad Museum, the oldest surviving train station in the United States, and the Ellicott City Colored School, a one-room schoolhouse that offers insights into the town's African American history.
The town also hosts several annual events, including the popular Main Street Music Fest, which celebrates local music and culture each September. Ellicott City's geographic setting along the Patapsco River certainly provides a picturesque backdrop for outdoor activities, too, including hiking and biking in nearby Patapsco Valley State Park.
Easton
Easton is another pretty small town on the state’s Eastern Shore that often falls under the radar of tourists. Established in 1710 and one of the oldest towns in Maryland, Easton quickly grew as a center for government and commerce, something that can still be seen in the town’s elegant historic district. Take a stroll here, and you’ll find around 900 immaculately preserved buildings dating from the 18th and 19th centuries, among them the Talbot County Courthouse and the Third Haven Meeting House, one of the oldest Quaker meeting houses in the United States.
Today, Easton is a hub for the arts and culture on the Eastern Shore, with numerous galleries, theaters, and music venues. The Academy Art Museum, located in a historic building, offers rotating exhibits of contemporary and traditional art, as well as educational programs for all ages. Easton is also known for its annual Waterfowl Festival, a celebration of the region's wildlife and heritage that attracts thousands of visitors each November.
Berlin
While overshadowed somewhat by its proximity to Ocean City, Berlin is located just a few miles inland and offers a pleasant contrast to its neighbor’s bustling beach scene. Founded in the early 19th century, Berlin has retained much of its historic charm, with the Victorian-era charm of its downtown area now preserved on the National Register of Historic Places. The town's name is derived from the 18th-century Burleigh Inn, a popular stopover for travelers that eventually evolved into the town of Berlin.
In-town attractions include the Calvin B. Taylor House Museum, a restored 19th-century mansion that offers a glimpse into the town's past, and a downtown area boasting many charming shops, galleries, and restaurants, many housed in historic buildings. Berlin also serves as a great base from which to explore other parts of Maryland. Surrounded by nature, Assateague Island National Seashore and its famous wild ponies are just a short drive away, while other great places to visit on Maryland's Eastern Shore are also easy to get to from here, such as the Pocomoke State Forest.
The Final Word
Maryland's small towns, despite being overshadowed by the state's larger cities when it comes to tourism, offer a unique window into the region's fascinating history, its rich culture, and its outstanding natural beauty. Together, these six undiscovered small towns in Maryland provide a quieter, more intimate travel experience, with plenty of opportunities to explore some of the East Coast’s best-preserved historic districts and scenery.
