11 Most Underrated Cities In Maryland
Maryland is renowned for its blue crabs, Chesapeake Bay, and pivotal role in American history, but there is far more to discover in the Old Line State. Beyond Baltimore and Annapolis, hidden gems offer a mix of fascinating attractions, gorgeous landscapes, and neighborhoods full of character. Did you know Maryland is home to the first railroad in the US or that it boasts the country’s oldest continuously operating ferry in Chestertown? Havre de Grace, named one of America’s best small towns, captivates with its harbor-front charm and duck Decoy Museum. Cumberland is a gateway to the Great Allegheny Passage, a paradise for cyclists, while Frederick is a hub for Civil War history and eclectic dining. These cities reveal Maryland’s lesser-known treasures waiting to be explored.
Cumberland
Nestled in the Allegheny Mountains, Cumberland is a treasure trove of history and outdoor adventure. Known as the "Gateway to the West," this city is also a gateway to the Great Allegheny Passage, a 150-mile trail that is a paradise for cyclists, offering spectacular outlooks and a connection to Pittsburgh. Cumberland is also home to the Western Maryland Scenic Railroad, which has train rides through the picturesque mountains and countryside. The nearby C&O Canal National Historical Park is another haven for cyclists and hikers, featuring miles of well-preserved towpaths.
At Rocky Gap State Park, you will find Lake Habeeb, renowned for its crystal-clear waters and excellent fishing for bass, trout, and sunfish. The lake’s North Shore is particularly popular for kayaking and picnicking. Take a stroll through Cumberland’s main streets and admire the impressive Emmanuel Episcopal Church, known for its Gothic Revival architecture and original Tiffany stained-glass windows.
Havre de Grace
Located at the confluence of the Susquehanna River and the Chesapeake Bay, Havre de Grace is a picturesque city with a rich maritime heritage. The Concord Point Lighthouse, one of the oldest in the state, provides stunning sights of the bay. History buffs can explore the Havre de Grace Maritime Museum, which highlights the region's significant role in Chesapeake Bay commerce. For a more quirky option, check out the Havre de Grace Decoy Museum to see a variety of working duck decoys.
Take in the outdoors at Susquehanna State Park, where trails like the Rock Run Grist Mill Trail and the Deer Creek Trail have paths for hiking. Anglers and birdwatchers will be thrilled by the park and can spot species like bald eagles, great blue herons, and scarlet tanagers. Downtown Havre de Grace pulls in visitors with its boutiques and restaurants, including The Vineyard Wine Bar, celebrated for its extensive wine selection and gourmet small plates in a cozy setting.
Frederick
Frederick blends a small-town feel with big-city amenities, making it a dynamic yet underrated destination. Its towncenter boasts cobblestone streets, colorful murals, and an array of shops and eateries. Restaurants like the Tasting Room serve up gourmet cuisine, or try White Rabbit Gastropub for cozy casual dining.
Those who love getting outside will love Gambrill State Park. It has trails like the Catoctin Trail and the Yellow Poplar Trail, both showcasing lovely vistas and lookouts of the surrounding valleys. Stroll along Carroll Creek Linear Park with water gardens, pedestrian bridges, and public art installations. For water sports, the beautiful Monocacy River has boating and fishing.
Ellicott City
Ellicott City, on the Patapsco River, is a city with a mix of old-world charm and modern flair. The downtown area brims with antique shops and cozy cafes like Little Market Café, where you can listen to live music on weekends. The Baltimore & Ohio Railroad Museum, housed in the oldest surviving railroad station in the country, is well worth a visit. Don't forget the Thomas Isaac Log Cabin, a relic of the city’s 18th-century beginnings.
Explore Patapsco Valley State Park. Trails like the Cascade Falls Trail and Grist Mill Trail both include scenic waterfalls and lush forests. The park’s Swinging Bridge is another must-see for a touch of adventure. For something unique, visit Clark’s Elioak Farm. Open from April to November, it houses a whimsical collection of fairy tale-inspired sculptures and attractions.
Easton
Located on the Eastern Shore, Easton is an arts and culture hub surrounded by natural beauty. The city hosts the annual Waterfowl Festival, a three-day event that celebrates the region’s wildlife heritage with art exhibits, retriever demonstrations, and birdwatching tours. Art fans will appreciate the Academy Art Museum. It has rotating artist spotlights and hands-on workshops. Foodies can dine at Out of the Fire, renowned for its wood-fired cuisine and fresh, locally sourced ingredients.
Explore the Pickering Creek Audubon Center, where trails like the Farm to Bay Trail and the Wetlands Edge Trail wind through lush wetlands known as Pickering Creek Wetlands. These trails have opportunities to see migratory birds like egrets and wood ducks while enjoying the serenity of this preserved landscape.
Berlin
Often called the "Coolest Small Town in America," Berlin lives up to its reputation with its lively and welcoming atmosphere. Located near Assateague Island, Berlin is surrounded by nature, including the tranquil waters of Stephen Decatur Park, a perfect place for boat rentals, picnics, and birdwatching. The town itself brims with character, featuring locally-owned shops and cafes like Blacksmith, known for its farm-to-table fare and inventive cocktails.
Movie buffs will recognize Berlin as the filming location for Runaway Bride and Tuck Everlasting, adding a touch of Hollywood allure. Don’t miss Main Street, where seasonal festivals and events like the Berlin Fiddler’s Convention bring the community together. For more adventures, visit nearby Assateague State Park, where wild horses roam freely on the beaches, creating a truly unforgettable experience.
Chestertown
Chestertown sits on the Chester River and is a historic city steeped in colonial past. Because of the Washington College, the town exudes an academic vibe complemented by its riverfront. The Chester River Packet, the country’s oldest continuously operating ferry, offers a unique way to experience the scenic beauty and ties to the past. The Chestertown Farmers’ Market is a must-visit for fresh produce, artisanal goods, and local crafts, providing a true taste of the community. Stop by the Schooner Sultana, a meticulously crafted replica of an 18th-century ship that has educational tours and sails up and down the Chester River.
For nature lovers, the nearby Eastern Neck National Wildlife Refuge has trails like the Tundra Swan Boardwalk, perfect for sighting waterfowl and other wildlife. After exploring, enjoy a meal at The Kitchen at the Imperial for elevated comfort food, or taste artisan pastries and coffee at Evergrain Bread Company. Seasonal events like the Chestertown Tea Party Festival further add to the town's timeless appeal.
Solomons Island
Solomons Island is at the mouth of the Patuxent River and is a beautiful community with a relaxed vibe and stunning views. The Calvert Marine Museum showcases the area’s maritime roots and features exhibits on paleontology, aquariums, and the historic Drum Point Lighthouse. Art lovers will appreciate the Annmarie Sculpture Garden & Arts Center, where sculptures are thoughtfully displayed in a natural wooded setting.
Travelers can indulge in fresh seafood and waterfront dining at The Pier or embark on a sunset cruise on the Chesapeake Bay for breathtaking views. Adventurists will love kayaking around Solomons Harbor or hiking the trails at Flag Ponds Nature Park, where you can also search for fossilized shark teeth on the shoreline. The Cove Point Lighthouse is one of the oldest continuously operating lighthouses in the state. Stop by the Solomons Island Boardwalk for picturesque strolls and boutique shopping.
Cambridge
Set on the banks of the Choptank River, Cambridge is a city full of impactful stories and natural beauty. The Harriet Tubman Underground Railroad Visitor Center provides a profound exploration of the region’s pivotal role in American history, honoring Tubman’s life and legacy. Blackwater National Wildlife Refuge is a must-see. Hike the Marsh Edge Trail, for a chance to spot bald eagles and great blue herons.
Stroll along the harbor and see the Choptank River Lighthouse, a replica of the original screw-pile lighthouse. Try some fresh seafood at Jimmie & Sook’s Raw Bar and Grill, or savor a meal with a view at Snappers Waterfront Café. For a cultural touch, stop by the Dorchester Center for the Arts, which showcases local talent through exhibits and workshops.
Hagerstown
Known as the "Hub City," Hagerstown is a mix of culture and outdoor recreation. The city is near the Antietam National Battlefield, a historic Civil War site where visitors can learn about one of the most pivotal battles in American history. Explore Greenbrier State Park, which features a gorgeous lake ideal for swimming, fishing, and picnicking, as well as hiking trails with stunning mountain views.
Downtown Hagerstown boasts the Maryland Theatre, hosting live performances ranging from concerts to Broadway shows and several art galleries like the Washington County Museum of Fine Arts. Don't miss the Hagerstown City Park for additional outdoor activities. At the end of the night, dine at Schmankerl Stube for Bavarian food or Broad Axe for elevated pub grub.
Laurel
Laurel is between Baltimore and Washington, DC, yet is often overlooked despite its old roots and beautiful landscape. The Montpelier Mansion, a historic plantation home, offers a glimpse into the area’s past with beautifully preserved architecture and gardens. Lake Elkhorn provides a peaceful retreat for walking and picnicking, with a lovely trail encircling the lake.
Laurel’s downtown features cute shops, local dining options, and lots of charm, such as Oliver’s Old Town Tavern, known for its warm atmosphere and delicious American fare. Visitors can check out Patuxent Research Refuge, a sanctuary for animals with miles of trails, birdwatching opportunities, and a visitor center. For a cultural experience, head to the Laurel Museum. It highlights the town’s history in the railroad industry and its development over the years.
Maryland’s underrated cities are brimming with character, with everything from landmarks and parks to vibrant arts and culinary scenes. These destinations showcase the diversity and atmosphere of the state, providing experiences for every kind of traveler. Whether you are exploring the rivers of Cambridge, the artsy vibe of Easton, or the nautical Solomons Island, Maryland’s lesser-known cities are waiting to be discovered. Plan a trip and uncover the places that make Maryland a destination like no other.
