Aerial view of Cumberland, Maryland.

6 Small Towns In Maryland With Big Charm

Maryland may be a small state, but it explodes with charm and natural beauty, featuring a diverse landscape of sprawling shorelines and towering mountains. Once a center of military activity during the Civil War, the state also overflows with a storied past and unique history, dotted with colonial buildings, intriguing museums, and several Civil War Trails. Aside from its beauty and rich history, the state houses a welcoming and charming community. Visitors may delve into Mid-Atlantic life, enjoy scenic drives along the mountainscapes, or unwind on local beaches, indulging in the most charming and quaint small towns of Maryland.

Havre de Grace

Havre De Grace, Maryland, on a summer day
Havre De Grace, Maryland, on a summer day.

Havre de Grace is located on the shores of the Susquehanna River and the head of Chesapeake Bay, and home to 1827 Concord Point Lighthouse, which is Maryland's second-oldest lighthouse. The town beautifully merges the rich history of Maryland with its natural beauty, featuring waterfront views and opportunities for visitors to enjoy guided Havre de Grace Museum Tours. There are even ghost tours of the town for those inclined to learn about any spooky spirits, while a trip to Concord Point Park or David Craig Park offers a chance to enjoy the natural scenery of the area. The Lower Susquehanna Heritage Greenway is another great spot to delve into Havre de Grace's beauty, linking trails along land and water.

Ocean City

Aerial view of Ocean City, Maryland.
Aerial view of Ocean City, Maryland.

Ocean City is one of the Atlantic Coast's most charming beach towns, earning the nickname "White Marlin Capital of the World" for its White Marlin population and famous for its 3-mile boardwalk. The boardwalk houses an arcade, a Ferris wheel, and a mini-amusement park. It is also a great destination to watch fireworks coloring the sky above the ocean, making it an ideal location for Fourth of July celebrations. On the water, travelers may enjoy fishing on the pier, parasailing, kayaking, surfing, or even taking boating tours. There are also plenty of activities on land, including golfing, touring the historic Ocean City Life-Saving Museum, or partaking in Chesapeake Ocean City Ghost Walks.

Berlin

Historic downtown of Berlin, Maryland.
Historic downtown of Berlin, Maryland.

Berlin features a main street that bustles with excitement no matter the time of year. Travelers may tour the downtown and discover beautiful local art at spots like Henry Fine Arts Gallery, Jeffrey Auxer Designs, Blown Glass Studio and Gallery, and Wooden Octopus. Popular attractions in the area include the Mermaid Museum, as well as 47 historic sites from the Federal, Victorian, and 20th Century, including the Calvin B. Taylor House Museum. There are plenty of hiking and biking trails for outdoor adventurists, while Heron Park is an ideal spot for birdwatching.

Saint Michaels

St. Michaels waterfront and marina.
St. Michaels harbor.

One of the most gorgeous towns to visit in Maryland, Saint Michaels (St. Michaels) offers proximity to the Chesapeake Bay, the city of Baltimore, and Washington D.C. The historic town boasts a beautiful harbor where visitors and locals alike enjoy boating, paddleboarding, canoeing, or jet skiing. The Chesapeake Maritime Museum is a unique spot to delve into, featuring a collection of Chesapeake Bay artifacts, exhibitions, and vessels, as well as a picturesque 18-acre waterfront and beautiful outdoor area. The Classic Motor Museum offers another glimpse into history, perfect for car enthusiasts. There are also several annual festivals for travelers to enjoy, including WineFest, Running Festival, and Oysterfest.

Leonardtown

Entrance to the Leonardtown Wharf, Maryland.
Entrance to the Leonardtown Wharf, Maryland. Image credit: Elvert Barnes via Wikimedia Commons.

Leonardtown is one of the friendliest towns in Maryland, home to a quaint, walkable downtown square and home to several art galleries, such as the North End Gallery, Leonardtown Arts Center, and Patina + Stone Studio. Travelers may tour historic landmarks such as the 1798 Tudor Hill Mansion or even partake in the National Oyster Shucking Championship, an exciting annual event held in town. The Butterfly Trail is a lovely outdoor destination featuring brightly colored butterfly banners and flags, as well as hidden art installations hand-crafted by local artists. The First Landing Wine Trail is a great place to enjoy a glass of wine and beautiful views while kayaking along the Potomac River from the Leonardtown Wharf is a great way to watch the sun go down.

Cumberland

The charming town of Cumberland, Maryland.
The charming town of Cumberland, Maryland.

Cumberland is one of the most unique Maryland towns, nestled within the Allegheny Mountains, part of the vast Appalachian Mountain Range. It is an excellent destination for hiking, mountain biking, and camping, home to the Hillcrest River Kampground and Evitts Creek Campsite and overflowing with trails and natural scenery in the nearby Wills Mountain State Park. Travelers may also enjoy a journey along the Western Maryland Scenic Railroad, which traverses along the mountainous terrain between Cumberland and Frostburg, Maryland. There are even Murder Mystery Dinner Train Rides, perfect for those looking to enjoy a scenic ride and exciting interactive dinner show. Canal Place Heritage Park offers visitors the perfect opportunity to delve into the town's past, tour George Washington's cabin, bike the C&O Canal Towpath or explore a Canal Boat replica.

Enjoy A Trip To Maryland!

The state of Maryland houses 18 scenic byways where visitors can view its beauty on land, as well as plenty of waterfront villages where travelers may explore the waters of the Chesapeake Bay. From fresh-caught cuisine to museums that tell tales of the state's rich history, there is plenty for visitors to see and do. Whether the beauty of downtown Berlin draws you in or the towering Concord Point Lighthouse of Havre de Grace piques your interest, the charm of the small towns of Maryland is unforgettable, promising the trip of a lifetime.

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