12 Small Towns in Maryland that Were Ranked Among US Favorites
Maryland, often celebrated for its bustling cities and picturesque coastal destinations, also boasts an array of charming small towns that have quietly risen to the ranks of favorites among U.S. travelers. From the tranquil streets of Berlin, where history meets artistry, to the colonial time capsule of St. Mary's City, where the past comes alive, and down to the Chesapeake City's serene canal-side charm, Maryland's small towns have something special to offer. Each town unveils a unique narrative, with museums, historic sites, and hidden wonders awaiting exploration. Visitors can savor the essence of Maryland's diverse identity, from maritime traditions to colonial roots, and indulge in regional cuisine that reflects the state's bounty from the Chesapeake Bay. So, why not add these gems to your travel itinerary and uncover the authentic soul of Maryland?
Havre De Grace
As the sun kisses the Susquehanna River, Havre De Grace awakens in all its maritime glory. As you cross the stunning Thomas J. Hatem Memorial Bridge, you will see picturesque views of sailboats dancing on the bay's shimmering waters. Nature enthusiasts will be mesmerized in Susquehanna State Park, where hiking trails lead to the majestic Rock Run Grist Mill. You can also discover the region's lesser-known, the jaw-dropping King and Queen Seat, a natural rock formation with a thrilling legend. And don't skip out heading to Concord Point Lighthouse. This 19th-century beacon guided ships through treacherous waters and offers dazzling bay beauty. As you wander along the Promenade, be sure to spot the mysterious "Poe Toaster," who pays annual homage to Edgar Allan Poe near his memorial.
Boonsboro
It's a journey to the center of the Earth, right in Boonsboro. You get to explore Crystal Grottoes Caverns, Maryland's only show cave, where you can marvel at the subterranean wonder of stalactites, stalagmites, and underground pools. You can step into the pages of a novel at Turn the Page Bookstore, owned by bestselling author Nora Roberts' husband, and if you're lucky, you might even catch a book signing event. Refuel at Dan's Restaurant and Tap House, a local favorite known for its craft beer selection and hearty dishes. You can also schedule a visit to the Pry House Field Hospital Museum, which played a crucial role during the Battle of Antietam. The museum showcases artifacts and stories from this pivotal Civil War battle.
Kensington
Just a stone's throw from the bustling heart of Washington, D.C., lies the charming enclave of Kensington, where suburban tranquility and artistic vibrancy booms at every corner. Head to the nearby Wheaton Regional Park for a day of outdoor fun. Hidden amidst its acres is the beautiful Brookside Gardens, a blooming oasis with vibrant flora and serene koi-filled ponds. The Kensington Armory is where you will find the Kensington Arts Theatre and the Montgomery Art Association Gallery. You should check their schedules for captivating performances and exhibitions that showcase the town's creative talent. Kensington Antique Row will delight and surprise you with its classic furnishing, antiques, and everything in between at The Cusp of Extinction, Goldsborough Glynn Classic Furnishings & Finds, and Starr’s Antiques & Collectibles.
Berlin
About 30 miles from Delaware, Berlin welcomes you with its charming streets straight out of a postcard. The Atlantic Hotel, a beautifully restored Victorian-era establishment, proves to be a fantastic first stop with its elegant façade and luxurious accommodations. Discovery awaits you at Burley Oak Brewing Company, where craft beer enthusiasts can enjoy innovative brews. Their experimental approach to brewing sets them apart. You can also visit the Calvin B. Taylor House Museum, a historic treasure trove showcasing Berlin's rich past. You can uncover the town's history, including its role as a hospital center during the Civil War, through its exhibitions, local author sessions, and storytelling sessions. Don't forget to discover the collection of Victorian mourning jewelry, a captivating and somewhat eerie glimpse into the past.
St. Michaels
The maritime wonderland and the "Heart & Soul of the Chesapeake Bay," St. Michaels, bring you the Hooper Strait Lighthouse. Here, you can check out the working boatyard and discover the craft of shipbuilding, see exhibits on oystering, or step aboard for breathtaking bay views. You can also hop aboard the Winnie Estelle, an oyster buy boat, and learn about the region's oyster-harvesting history for an experience like no other. St. Michaels is renowned for its boutique shopping along Talbot Street, where you can step into charming stores like The Preppy Redneck and The Treasure Chest for unique finds, from nautical-themed jewelry to coastal home decor. For a taste of the bay's culinary delights, head to the Crab Claw, where you can indulge in fresh, steamed blue crabs while overlooking the water, or the Miles River Yacht Club, where you can savor fresh seafood.
Chestertown
As you stroll down the brick-lined streets of the timeless Chestertown, you will get a glimpse of the vibrant culture. You can take a trip to the historic Emanuel Churchyard, the final resting place of notable figures like George Washington's aide-de-camp, Tench Tilghman. Chestertown's artistic spirit is on full display at galleries like the Carla Massoni Gallery, showcasing the work of regional and nationally recognized artists. Don't miss the RiverArts Gallery, where you can admire various artworks, from photographs to pottery to paintings. You can also stop by the Custom House, a historic site that now houses the Chestertown Visitor Center. Here, you can gather information about the town's attractions and events, including the Chestertown Tea Party Festival, a lesser-known celebration of the local colonial heritage.
Oxford
Founded in the 17th century, Oxford emerges like a pearl in a hidden oyster. You will find an 18th-century tavern room, a time capsule of colonial life, a collection of ship models intricately crafted by local artisans, and artifacts from the shipwrecks in the Oxford Museum. You should also keep an eye out for the Skipjack Nathan, a historic wooden sailing vessel that occasionally graces the harbor with its majestic presence. Oxford's culinary scene is a testament to its waterfront location. You can savor the freshest seafood at the Oxford Market and enjoy views of the Tred Avon River. Or indulge in a gourmet meal at the Masthead at Pier Street, where you can dine right on the water's edge.
St. Mary's City
Step into a living history book as you arrive in St. Mary's City, a town that allows you to experience Maryland's colonial roots like no other. Established in 1634, it's a place where history comes alive on every cobblestone street. Your journey begins at Historic St. Mary's City, a remarkable outdoor museum. You can explore the reconstructed State House of 1676 and the Print House, where you can witness the printing of colonial documents. Don't miss the Maryland Dove, a replica 17th-century ship that provides insight into early maritime life. A hidden gem in this historic town is the Woodland Indian Hamlet, an intriguing wonder that portrays the lives of indigenous peoples in the 17th century. You can also dine like a colonist at the nearby Brome-Howard Inn, offering a menu inspired by colonial-era recipes. Or head to the Green Door Tavern for a cozy atmosphere and classic American fare.
Crisfield
As you arrive in Crisfield, the briny breeze and the sight of watermen at work will set the tone for your visit. The J. Millard Tawes Historical Museum allows you to explore exhibits on the town's history and its significance in the world of crabbing and oystering and dive deep into the lore of Chesapeake watermen. Don't forget to admire the exhibit on the legendary Chesapeake skipjack, providing a glimpse into the world of oyster dredging. A must-do in Crisfield is a boat tour to Smith Island to discover a unique culture, indulge in Smith Island cake, and witness the island's picturesque landscapes. Also, sample fresh crab dishes at the Watermen's Inn or dive into a seafood buffet at the Crisfield Crab Place.
Ocean City
Ocean City is a town where the rhythms of the Atlantic Ocean set the pace, and the fun never stops. Your Ocean City adventure begins on the iconic boardwalk, where you can savor the scent of saltwater taffy at Dolle's Candyland and enjoy thrilling amusement park rides at Trimper's Rides. Ocean City is a watersports paradise, with options for jet skiing, parasailing, and paddleboarding. The town's sport fishing is legendary, and you can book a charter for a chance to catch marlin, tuna, or striped bass. When the sun sets, the Ocean City nightlife comes alive. Fager's Island offers waterfront dining with live entertainment, and Seacrets, Jamaica USA boasts a lively atmosphere with multiple bars, stages, and a bayfront beach.
Cumberland
Once a vital transportation hub, Cumberland beckons travelers with its stunning natural beauty and rich railroad history. The C&O Canal Towpath offers endless hiking and biking opportunities. While Deep Creek Lake, a short drive away, is perfect for water sports and relaxation by the water. You can take a short drive to the Paw Paw Tunnel on the Chesapeake and Ohio Canal. You can admire this engineering marvel, carved through the mountain, as you walk the towpath alongside the tranquil waters of the canal. Cumberland's vibrant arts scene comes to life at the Allegany Arts Council, which hosts rotating exhibitions, workshops, and live performances.
Chesapeake City
Imagine a place where narrow streets wind their way past quaint shops and charming cafes, and boats lazily drift through a picturesque canal. That's Chesapeake City. Housed in the historic Lockkeeper's House, the Chesapeake City Museum lets you discover the town's role in canal history, including tales of mule-drawn boats and lock operations. You can also book a canal boat ride with Chesapeake City Water Tours. You will glide along the canal, passing under the soaring Chesapeake City Bridge, and learn about the town's history and the bustling maritime traffic. You should also have a taste of the tapas and seafood dishes at Schaefer's Canal House, a historic waterfront restaurant with stunning canal views. And for dessert, visit the charming Bayard House Restaurant, famous for its decadent crab imperial.
Maryland's small-town favorites have earned their reputation not through fleeting charm but by offering real-time experiences that resonate with travelers. From the lip-smacking seafood of Crisfield to the maritime heritage of Chesapeake City, these communities celebrate their roots with open arms. Culinary delights, historic treasures, and a warm local welcome await. It's not just about visiting; it's about being part of the story, one that unfolds in real time and stays with you long after you have left.
