8 Maryland Towns That Rival Europe's Best
Maryland was among the initial Thirteen Colonies, the seventh to enter the Union, and achieved a "Free State" recognition in 1864. Although predominantly British during colonial times, the sobriquet "America in Miniature" draws from the state's natural diversity and various heritage backgrounds. Seaside allure and European influences unite in many small towns, like Oxford's unique picket fences.
The capital was named after a princess from Denmark and Norway, while names like Cambridge and Berlin set the stage for wanderlusty tourists whose imagination does the rest to make the Old Line State look a bit more European. With many rivers converging into the world's biggest estuary, Chesapeake Bay, the Eastern Seaboard state, is the perfect place for an upcoming summer getaway reminiscent of a European vacation.
Annapolis
Maryland has one of the nation's smallest and most gorgeous capitals, which also goes by the "Sailing Capital of the World.” Settled by the Puritans in 1649, who called it "Providence," Annapolis boasts a deep heritage in maritime trade, home to the U.S. Naval Academy since 1845. The harbor has long been the beating heart of Annapolis. Named after Princess Anne of Denmark and Norway, it is one of the best, most storied places to visit along the East Shore. So explore this incredibly historic coastal city and its very personal bond with the sea.
Snug on the Chesapeake Bay and Severn River; seafood is everywhere. Take up sailing, a fishing charter, or the family-favorite Pirate Adventures on the Chesapeake. Meanwhile, there are pavilions, formal gardens, and galleries along the paved trails at the 340-acre Quiet Waters Park. Before leaving, don't miss Seasons Olive Oil & Vinegar Taproom for a drink and Sweet Hearts Patisserie for European delights.
Bel Air
This town with a charming name and German heritage at “the Heart of Harford County" is 30 miles northeast of Baltimore. Bel Air's storybook downtown houses shops, restaurants, and fun for all ages. Like an authentic European town, Bel Air values moments of intimacy, relaxing, and socializing with nooks like Cozy Cookies and Looney's Pub. Along its tree-lined streets winding around greens and welcoming amenities, Bynum Park has scenic water views, and Rockfield Park offers sports facilities, a large playground, nature trails, and a historic events home.
On a historical note, the federal-style Hays House Museum displays the turn-of-the-19th-century American lifestyle with relics and exhibits. To the north, Enotria Restaurant & Grill is a relaxed Italian eatery with a bar serving brick-oven pizza and homemade pasta in an old-world vibe. Das Bierhalle and vineyards in the area, like Harford Vineyard & Winery, transport you for an evening overseas.
Berlin
Despite what its name suggests, Berlin was not named after the German capital but rather a contraction of "Burley Inn," a historic inn that once stood in the area. With origins dating back to 1677, this charming town on the Eastern Shore carries a unique blend of colonial architecture, artistic energy, and coastal charm. Berlin’s Main Street is the heart of the town, lined with antique shops, cozy cafés, and historic buildings that exude European finesse. The Sterling Tavern is a top spot, with delicious wings and a social vibe. A Maryland Arts & Entertainment District, Berlin fosters a vibrant creative scene with art galleries, live performances, and local festivals, bringing the community together year-round. Among its most striking landmarks is the Atlantic Hotel, an imposing red-brick building at the town’s center, offering an immersive stay in history.
With its deep connection to the Chesapeake Bay, Berlin is a town shaped by its maritime past. Naval officer Stephen Decatur was born here, and local shops and cafés reflect this nautical heritage in their décor and offerings. Many visitors stop in Berlin on their way to Ocean City, making it a beloved detour on a classic Maryland road trip.
Cambridge
Cambridge exudes seaside enchantment along the scenic banks of the Choptank River. Settled in 1684 as one of Maryland’s firstborns, this Dorchester County town is among the nation's oldest colonial cities. Starting the day, Long Wharf Park is a great place to soak in the charm, an area full of beautiful houses and views of the Choptank River Lighthouse, a replica of a classic 1871 lighthouse.
From the inception to when Harriet Tubman was enslaved here as a youth, the Harriet Tubman Museum and Education Centre is easily spotted with a mural outside in the town center. Visit the plantation she lived on just a few miles south for a tour. Furthermore, the Harriet Tubman Underground Railroad Visitor Center reiterates the story of a woman of color in captivity. Back in town, visitors can take a leisurely stroll along the High Street, which is lined with shops, restaurants, and unique museums, along with aesthetic scenery.
Easton
Founded in 1710, Easton grew around the 20-by-30-foot brick Talbot County Courthouse, the town’s first official building. Initially known as Talbot Courthouse, the community was renamed Easton in 1788 and soon became a hub of commerce and culture on the Eastern Shore. Today, this charming town is a perfect family adventure or romantic escape, with Easton Point Park offering a scenic retreat. Its grand European-inspired architecture is best seen at the circa-1820 Academy Art Museum, where art exhibits, concerts, and dance performances bring creative energy to the town.
A deeper look into Easton’s past comes alive on the Chesapeake Ghost Tour, beginning at the storied Tidewater Inn. Originally a Victorian hotel, it was rebuilt after a fire in the mid-1900s and is now a rustic accommodation. Just next door, the Avalon Theatre, once a vaudeville house, continues to host performances, with eerie tales of a mysterious actress’s murder in the elevator adding intrigue. End the day with a sweet treat from Bonheur Ice Cream and Pie or a classic Chesapeake meal at the Tidewater Inn’s Hunters' Tavern.
Hagerstown
Rooted in German settlement, Hagerstown's historic downtown is rife with architecture. The sturdy red brick buildings offer understated European charm stark against the surrounding landscape. A copious amount of attractions await families and history lovers, like the City Park Train Hub, at the heart of Maryland's scenic valley. Catch the Appalachian Trail by the tail or a kayaking opportunity along the Potomac River.
Get a German pretzel for a stroll through Hagerstown City Park, around a scenic pond with a bridge and fountain, shady picnic zones, and a kids' splash pad. The fine arts museum on-site hosts a rotating collection of American and European art of over 6,000 paintings and sculptures from between the 18th and 20th centuries. For a different type of art, opt for a performance at the stately 1915 Maryland Theatre, with balcony and box seats.
Oxford
Oxford is full of English vibes at the confluence where the Tred Avon River and Choptank River converge into the bay. The town's distinct configuration offers water views from nearly every point. As one of the state's oldest towns, Oxford was a huge and wealthy port for decades, only second to Annapolis by the number of incoming ships coming in, and it thrived by exporting goods to Britain. Testament to its past, Oxford Day celebrates its longtime, which comes every year in late April. The event boasts everything from a community dog walk and outdoor competitions to a bake sale and food stalls.
The small town has a scenic, swimmable beach, with access from Strand Street and one at Oxford Town Park. Dockside Boat Rentals offers rentals for kayaks, paddle boats, or bikes along the nearby trails. As the day ends, Doc's Sunset Grille is a must-stop crab house overlooking the bay.
St. Michaels
Once known for shipbuilding and seafood processing, St. Michaels did not catch tourist fever until the last half-century. At the 18-acre waterfront Chesapeake Bay Maritime Museum, you can try the local art of oystering and learn about bayside life through exhibits, activities, and boat rides. Among historic houses and architecture, the local St. Michaels Museum is a charming 19th-century home with regional history exhibits and walking tours. Moreover, the 1870s Hooper Strait Lighthouse, which has a sea hatch and lookout, is a preserved 19th-century historic landmark that has moved here from the middle of the bay.
For a different experience, one can enjoy wine tasting and wildlife views aboard Sail Selina II, which is perfect for couples. The seaside charisma on the vast Miles River is akin to that along the Seine, with houseboats and boat tours. Follow up with an intimate evening at St. Michael's Winery, featuring 18 wine styles in a quaint, all-season tasting room and a retail shop. After a fun day out, the Inn At Perry Cabin is a cherry on top of every perfect getaway with a touch of understated European luxury.
Wrapping Up
These towns have a historical and/or cultural flair comparable to beautiful European cities. It's fun picking up on European cues through lovable features and favorite pursuits in each, and suddenly, you're having grand fun in Europe. So, free up a weekend to feast on local crab by the bay, try oystering, and stay at the elegant Tidewater Inn, the place to be and be seen.
