These 9 Towns Are Maryland's Best-Kept Secret
Between captivating coastal vistas, delectable seafood dishes, fascinating maritime museums, and significant Civil War-era sites, the "Old Line State" is an extraordinary place to explore. If you go beyond the well-beaten path to discover destinations more under the radar, you will find hidden gems that will leave you in awe. From St. Michaels to Oakland, these towns are Maryland's best-kept secrets, featuring natural, historical, culinary, and cultural treasures.
St. Michaels
Located along the breathtaking Miles River, St. Michaels is a charming destination as pretty as a postcard. Soak in the stunning scenery, wandering through Waterfront Park, before you make your way to the Chesapeake Bay Maritime Museum. Between world-class exhibitions, original artifacts, visual arts, and even on-the-water experiences, this is a wonderful place to uncover the maritime history, culture, and environment of the entire Chesapeake Bay region. Grab your camera and capture striking photos of the 1879 Hooper Strait Lighthouse. This was the second lighthouse built at Hooper Strait, following the destruction of the first by ice in 1877. You can set out to explore the Miles River via Patriot Cruises, choosing between a 70-minute Narrated Historical Cruise featuring historic mansions and fascinating wildlife, a fun-filled Happy Hour Cruise adventure, or even a private charter for a more personalized journey.
Chestertown
If remarkably preserved 18th-century architecture, picture-perfect tree-lined streets, and scenic gems along the Chester River sound incredible to you, welcome to Chestertown. Experience the timeless charm as you search for hidden treasures in The Bookplate. Their specialties include regional Eastern Shore and Chesapeake Bay History. From there, see a mesmerizing performance at the Garfield Center for the Arts at the Prince Theatre, one of Maryland's best-kept secrets. From family-friendly musicals to modern stage classics and welcoming open-mic nights, you will be in for a real treat. Enter a world of nostalgia as you discover special gifts and one-of-a-kind souvenirs to take home with you in Twigs & Teacups. From lovely books to toys, apparel, kitchenware, and other gems, you never know what you may find here.
Chesapeake City
Originally called Bohemia Village, Chesapeake City adopted its current name in 1839, anticipating future growth and development. The city was officially incorporated in 1849 upon reaching a population of 400. Today, you can still see much of the 19th-century architecture remaining, with the south bank area listed on the National Register of Historic Places. Learn about the history of the canal that connects the Chesapeake and Delaware bays in the C&D Canal Museum. Here, you can see the liftwheel pumping plant of the original canal, and artifacts significant to the growth of American transportation and technology. Enjoy quality craft beer brewed on site in the Bayheads Brewing Company, followed by a serene stroll through Pell Gardens Park. This scenic waterfront park offers beautiful views of the water and the canal.
Berlin
The filming location of famous films like "Runaway Bride" starring Julia Roberts and Richard Gere, Berlin stands out for its architectural beauty and charm. Forty-seven structures are listed on the National Register of Historic Places, dating back to the Federal, Victorian, and 20th-century periods. Aside from its architectural wonders, Berlin also features intriguing landmarks such as the Mermaid Museum. Enter a world of enchantment as you come across these mystical creatures; you can even book an unforgettable Mermaid Photoshoot with a professional that both kids and adults will love.
From there, enjoy a magical evening in The Globe. This historical theatre has been operating for over a century, offering live music and events, along with craft beers, delicious food, and specialty cocktails. Head outdoors to visit Assateague State Park; two miles of ocean beaches, water boating opportunities, wildlife viewing, and even wild horses await. You will undoubtedly discover some of Maryland's best-kept secrets as you get to know Berlin.
Middletown
A destination both history buffs and architectural enthusiasts will love, Middletown is an incredibly eye-catching town. Discover striking attractions like the Washington Monument, a remarkable, rugged stone tower. Constructed in 1827, this was the first monument completed in memory of President George Washington. You may also spot migratory birds from here, including falcons, eagles, and hawks, especially in mid-September. Another captivating site is the South Mountain State Battlefield. This significant landmark is dedicated to interpreting and preserving the first major Civil War battle that took place in Maryland—the Battle of South Mountain, fought on September 14th, 1862. Middletown also offers incredible scenery. Enjoy a picturesque stroll through Middletown Park, where you can explore scenic trails, a lovely fishing area, an amphitheater, fields, and sports courts.
Thurmont
Welcome to Thurmont, a gem in the foothills of the Catoctin Mountains—and one of Maryland's best-kept secrets. Often referred to as the “Gateway to the Mountains,” prepare to discover magical sights as you step into places like Catoctin Mountain Park. Hike through scenic trails with 25 miles of them to choose from, ranging in difficulty, uncover incredible views, and enjoy a magical night camping under the stars. Next, meet captivating creatures in the Catoctin Wildlife Preserve. From Arabian Camels to 30 different species of Amazon Parrots, Madagascar Lemurs, Eurasian Reptiles, and Giant Tortoises from the Tropics, animal lovers can prepare for an unforgettable international adventure. The Historic Roddy Road Covered Bridge is another notable landmark to visit. This 40-foot single-span Kingpost design bridge, constructed in 1856, is the smallest covered bridge in Frederick County today.
Ocean City
Spend some time in Ocean City, a picture-perfect beach oasis that feels like paradise. Get sun-kissed as you relax on the sandy shores of Ocean City Beach, or discover a world of entertainment as you meander down the Ocean City Boardwalk, where three miles of restaurants, shops, and family-friendly activities await. Not to mention, Ocean City is also home to Splash Mountain Water Park, featuring the exhilarating Master Blaster water roller coaster, 45-foot-tall half-pipe slide, river rafting Rapids Ride, and mysterious Black Hole. Plus, with ten racetracks at Speedworld and Jungle and Treasure Golf at Jolly Roger Mini Golf, Ocean City holds something in store for everyone.
North Beach
Plan a dreamy, serene escape to North Beach, one of Maryland's best-kept secrets. Unwind on the western shores of Chesapeake Bay as you lie back on the beach, or see the gorgeous rain gardens, shallow ponds, waterfalls, native plants, and historic structures of Mark R. Frazer Sunrise Garden. Stroll along the boardwalk at sunset, where calm waves meet the glowing sky in hues of pink and gold. Fuel up with a delicious espresso-based beverage, flavored scone, or mouth-watering muffin at “the bakist.” Finally, treat yourself to a rejuvenating deep tissue massage, hot stone treatment, or lymphatic drainage massage at Lotus Peace Massage, a perfect way to end a peaceful day by the bay.
Oakland
Between the "treasure trove" of exhibits covering the region's past at the Garrett County Historical Society Museum and the awe-inspiring 1920 Baldwin steam locomotive in the Oakland B&O Museum & Train Station, there are countless tales and stories waiting to be discovered in Oakland. Animal lovers can meet and greet furry creatures at Alpaca Acres Farm and Fun, situated near the beautiful Deep Creek Lake. You can also see the lovely Youghiogheny River, one of the longest rivers in Maryland, and the mesmerizing 53-foot waterfall in Swallow Falls State Park. After exploring the outdoors, take a quiet stroll through downtown Oakland, where local shops, cozy cafes, and friendly faces create a warm, welcoming atmosphere, surrounded by the charm of the mountains.
Discover Maryland's Hidden Gems
Whether you are planning an adventure the entire family will love, an unforgettable trip with loved ones, or heading on your own solo journey, The Old Line State is filled with treasures every type of traveler will love. From the magnificent maritime museums and structures of St. Michaels to the historic Civil War battlefields of Middletown and the stunning scenery and captivating creatures of Oakland, adventures await around every corner. These nine towns are Maryland's best-kept secrets!
