9 Prettiest Towns In Maryland
Maryland is a small state on the East Coast of the U.S., with Delaware, Pennsylvania, West Virginia, and Virginia bordering the state. It has many naturally beautiful locations, including the Chesapeake Bay and several gorgeous state parks. The Chesapeake Bay is a favorite location for sailing and fishing, while several inland communities afford fantastic outdoor excursions. Mountain climbers and hikers will also find plenty to do in Maryland since it is home to plenty of picturesque mountains and hiking trails. Sugarloaf Mountain in Frederick County is a favorite for its superb panoramic views of the surrounding landscape. Whether tourists seek a relaxing day in a small-town shopping or an exhilarating mountain hike, Maryland's prettiest small towns won't disappoint.
Boonsboro
Boonsboro is one of the oldest towns in Maryland, sitting near the state's Western border, not far from West Virginia. It gets its name from two of the town's early founders, George and William Boone, who were cousins of Daniel Boone. These early settlers established the township in 1792, although William Boone came to the area in 1778 and established a farm near what is now Potomac Street.
Visitors can learn more about its fascinating history and see some unique artifacts at the Boonsboro Historical Society. Or, they can check out the Boonsborough Museum of History on Main Street. The town also offers some awesome outdoor experiences, with Schafer Park and Boonsboro Pond near the town's center offering fun for the whole family. Boonsboro Pond is home to the town's fishing derby and is specially designed for children. Anyone hoping to capture Boonsboro's authentic outdoor beauty will love these locations.
Several large state parks nearby are also perfect for outdoor explorers. In particular, Greenbrier State Park and Crystal Grottoes Cavern provide fabulous glimpses of the region's geography and natural landscapes. Greenbrier State Park is ideal for hiking in the woods, while Crystal Grottoes Cavern offers guests a chance to view some naturally occurring crystals underground just over a mile from town.
Chestertown
Chestertown sits along the Chester River, with the Chesapeake Bay to the west, serving as a natural border between the state's two regions. Baltimore, D.C., and Boonsboro sit to the west of the Chesapeake Bay, while Chestertown sits to the east. Chestertown's history goes back to 1706 and is one of Maryland's oldest communities. Travelers to the township can visit Chestertown's Historic District and see some of the original and refurbished colonial-era houses lining the streets.
Chestertown has the second largest amount of historic buildings in Maryland, just after Annapolis. The John L. Stam House, built in the 1850s, is just one fine example of the historic structures in town. Much of the house still retains its original structure and appearance, meaning guests can experience an authentic glimpse into the town's early history. The White Swan Tavern, just a few minutes from the John L. Stam House, is another beautiful historic building worth checking out. This old tavern goes back to before the Revolutionary War and still serves the local community with home-cooked meals in a welcoming environment.
Saint Michaels
Saint Michaels is one of the best coastal communities in Maryland. It's well-known as a shipbuilding center, as well as having some excellent fishing and oystering. The town's roots go back to the early 1600s, with early settlers primarily subsisting through hunting and trade. It became a prominent trading post during the early colonies, with tobacco being one of the main exports. In 1677, locals constructed the Christ Episcopal Church of St Michael Archangel parish, which still stands today and is worth visiting.
Plenty of sites in town are perfect for marine life and boat lovers. The Steamboat Building and the Chesapeake Bay Maritime Museum offer guests a chance to experience the community's nautical past and present. Tourists are sure to love exploring the many boats docked in the town's bay and learning about how these waterways sustained the town for ages.
Rock Hall
Rock Hall is one of the best spots along the Chesapeake Bay to chill out, thanks to its stunning views and the laid-back lifestyle of the locals. The town began as a major crossroad in Kent County. In 1675, the town's name was Rock Hall Cross Roads, thanks to it housing one of the first roads connecting Kent County. These roadways once carried America's founders across the colonies, including George Washington and Thomas Jefferson.
As a community that predominantly sustained itself through fishing, it retains its roots in many ways. Today, the town is well known for its delicious seafood and beautiful marinas, with Osprey Point offering being one of the best locations. Osprey Point is a blend of marina, restaurant, and inn situated right along a bay known as The Haven. Those hoping to check out displays of old ships and fishing tools of the earlier settlers should visit Rock Hall Museum. The museum has replicas of ships as well as old scavenged artifacts from the sea.
Thurmont
Thurmont is one of the best locations for hiking in Maryland, with several parks and recreational areas both within town and nearby. Thurmont sits about two and a half hours west of Rock Hall, which is an inland town surrounded by woodlands and mountains. It began as Mechanicstown in 1751, its official date of incorporation, although there's evidence of settlers decades earlier. Most earlier settlers sustained themselves through the timber industry or as hunters and trappers. Big Hunting Creek served as an essential power source for these early settlers, with the water's flow powering mills along its banks.
Today, Thurmont is a nature lover's paradise. Big Hunting Creek is still one of the town's most valuable natural resources and a prominent location for fishing or hiking. Thurmont Trolley Trail is one of the best hikes and sites near the creek, offering a rare glimpse into the early years of the town's railway system. Other locations just outside the community grant stunning views of the surrounding wilderness and woodlands. The Middletown Watershed and Cat Rock & Bobs Hill Natural Area both provide breathtaking views of the mountains outside Thurmont and excellent hiking opportunities.
Leonardtown
Leonardtown is one of Maryland's most underrated towns, resting nearly three miles south of Thurmont. It touches Mcintosh Run, a charming small bay that connects the town to the larger Breton Bay. Leonardtown Warf is a lovely little park along Mcintosh Run and an excellent spot for a restful afternoon outside. History lovers will also love Leonardtown. Tudor Hall, not far from Mcintosh Run, is a fine example of colonial architecture built in 1744. Guests can explore the old house by booking an appointment. The home originally belonged to Philip Key, the uncle of the writer of the U.S. National Anthem and thus an important site for American history.
Oakland
Oakland, like Boonsboro, is one of Maryland's western townships situated near the borders of Pennsylvania and West Virginia. The city traces its history back to the founding of the Baltimore and Ohio Railroad when the train company decided to build a rail through the area in 1849. The town grew quickly as a prominent tourist attraction, with 1872 being its official incorporation date.
Anyone hoping to understand the town's railroad history better should visit the Oakland B&O Museum. Their exhibits include well-maintained steam engines from the 1800s. Although, this fascinating museum isn't the only place worth stopping by while in town. Just outside town is the Broadford Recreation Area near Broadford Lake. It's a great place to take kids, with the lake and playground offering hours of fun and exploration. Golf enthusiasts can also enjoy playing a few games at the Oakland Golf Club.
Monkton
Three and a half hours east of Oakland and a few miles north of Baltimore is the adorable town of Monkton. It's one of the most picturesque small towns In Maryland, with Big Gunpowder Falls being one of the loveliest waterways in Baltimore County. While not an officially incorporated community in Maryland, its history dates back to the 1700s when Robert Cummings, a native of Pennsylvania, became one of the earliest settlers.
The Monkton Hotel is one of the community's most notable historical landmarks, built in 1858. The hotel offers comfortable lodging on a site that's been integral to the community for over 150 years. It's also an excellent hub for launching out and experiencing what the area offers.
The hotel's cafe is excellent for home-cooked foods, fresh coffee, and meeting new people. The Monkton Bike and Tube is also right on the hotel's doorstep and a fun and exciting place to spend an afternoon. Visitors can rent a tube for a lazy ride down the river or a bike for cycling the nature trails in the area.
Hancock
Hancock rests snuggly between the borders of Pennsylvania to the north and West Virginia to the south. It isn't far from Oakland, which is just over an hour and a half drive west from Hancock. The Potomac River flows to the south of the community and serves as a natural boundary between this Maryland city and West Virginia.
Its one of the oldest towns in Western Maryland, and it even hosted George Washington a few times. The town gets its name from one of its early founders, Edward Joseph Hancock, Jr., who owned and operated a ferry business along the Potomac River. Although Hancock isn't just a community steeped in historical charm, it's also known as Maryland's Trail Town. It gets this nickname because of all the gorgeous nature trails crisscrossing the town's borders. The Western Maryland Rail Trail is one of the best places for tourists to explore, taking trekkers on a 28-mile journey through the town's natural beauty.
Exploring Maryland is an excellent way to kick back and relax in nature. The Chesapeake Bay, Eastern Marshes, and the Appalachian Mountains are just a few organic sites that showcase the state's charm and majesty. Maryland is also a state full of history, with native tribes living in the region since 3,000 B.C.E. Later, Maryland became one of the most critical states in the War for Independence and hosted several of the Founding Fathers on more than one occasion. Whether travelers want to better understand the nation's founding, check out of the hustle of life for a while, or go sailing on the Chesapeake, Maryland has it all.
