9 Prettiest Maryland Towns to Visit in 2024

A trip to the East Coast of the United States is incomplete without stopping to experience the allure of the Old Line State. Famous for its captivating heritage, sumptuous seafood scenery, and unmatched natural beauty, Maryland offers visitors charm beyond the bustle of busy Baltimore and neighboring Washington D.C. Scattered throughout the scenic landscapes are picturesque little towns providing an ideal break from the norm. Their slow pace of life and relaxed rural life introduce you to life's simple pleasures.

From Colonial-era ports hugging the Chesapeake to 19th-century river villages and picturesque mountain communities, exploring these delightful towns in Maryland pays off with architectural gems, iconic landmarks, and scenic vistas around every corner. If you have an East Coast itinerary in the near future, any of the following destinations will be an excellent addition.

St. Michaels

This Eastern Shore gem on the picturesque shores of Chesapeake Bay delights visitors with everything from Victorian-era architecture to gorgeous water vistas and delicious blue crab cuisine. Since its establishment in the mid-17th century, St. Michaels has experienced landmark events in the state's and country's existence, culminating in unprecedented historical heritage you can discover at the St. Michaels Museum. The Chesapeake Bay Maritime Museum profiles the town's nautical heritage by showcasing various vessels used for diverse maritime activities on the Chesapeake.

Exploring St. Michaels allows you to witness longstanding landmarks like the Hooper Strait Lighthouse, which dates back to 1879. Travelers also come to the town for its unique Chesapeake Bay cuisine, featuring luscious seafood you can sample at Foxy's Harbor Grille while taking in stunning ocean vistas.

Cumberland

Cumberland excites first-timers with spellbinding vistas of the Allegheny Mountain peaks. The town invites you to soak up the unmatched beauty that defines its outdoor landscapes during a soothing ride on the Western Maryland Scenic Railroad. The journey begins in downtown Cumberland, cutting through dense woodlands in the backcountry set against the backdrop of the Allegheny Mountains. Countless outdoor opportunities await throughout the 3,000-acre Rocky Gap State Park, from hiking and camping to boating on the 243-acre Lake Habeeb.

Moving to the downtown district, Cumberland harbors a quaint blend of museums, restaurants, and galleries to entertain visitors. The Allegany Museum details the region's curious past, while the Cumberland Theatre is a regional art hub known for staging compelling theatrical performances.

Cambridge

Cambridge takes tourists back to the Eastern Shore region, where an idyllic coastal setting and rich historical heritage highlight their vacation. The town presents several outdoor spaces designed for those who want to forget about their troubles and decompress. A good example is the riverside Long Wharf Park, which features a lengthy platform for lazy, uninterrupted strolls. At the end of the path, you will encounter the Choptank River Lighthouse, a replica of a historic town landmark with postcard-worthy visual appeal.

Cambridge is a historic community harboring rare memories of Maryland's formative years. The Harriet Tubman Museum and Educational Center is an excellent destination if you are curious about its history. The fine facility exhibits rare artifacts and screens short films delving into the history of enslavement, the Civil War, and the Underground Railroad, among other notable past eras.

Havre De Grace

Havre de Grace is a lovely Harford County community that is endearing to travelers for its rich museum scene, small-town atmosphere, and cozy natural scenery. Given the numerous historical markers dotting its territory, history lovers are in for a long and exciting lesson on the town's past. Havre de Grace hosts the Lock House Museum, which depicts interesting American history relating to canals and how they work. It also has the Havre de Grace Maritime Museum, which focuses on the area's maritime history.

The town's location on the Chesapeake Bay-Susquehanna River confluence results in awe-inspiring vistas that guests can take advantage of with a stroll along the Havre de Grace Promenade. Finally, do not forget to carry your camera, as you will want to get a snap of the beautiful Concord Point Lighthouse.

Berlin

Berlin is a gem in Worcester County and the gateway to Assateague State Park. It is home to a friendly community that takes pride in welcoming newcomers to explore its attractions. Visitors will get a sense of the overall camaraderie at the Berlin Farmers Market while interacting with local crafters and farmers. Downtown Berlin is a vibrant historic district with Victorian structures housing restaurants, museums, breweries, and other local businesses. The Calvin B. Taylor House transports guests to 19th-century Berlin by letting them explore its rare antiques and memorabilia.

Elsewhere, the Mermaid Museum reveals a quirky side to Berlin with an unusual display of mermaid-related merchandise, apparel, souvenirs, decor items, and more. After your escapades around the town, stopping at Burley Oak Brewing Company for a pint of locally crafted beer is one of the best ways to wrap up the day.

Oxford

Oceanside getaways make for some of the most picturesque towns to visit in Maryland, and Oxford is right up there with the best, especially if you prefer to avoid the crowds. Its waterfront location assures visitors of remarkable opportunities on the water. Safe Harbor Oxford Marina provides access to boat charters for an easygoing sail to discover the town from the water. The Oxford Museum downtown helps preserve the community's historical heritage. It exhibits a range of archives and artifacts chronicling landmark events in the town through the years.

Meanwhile, culinary enthusiasts can look forward to sampling sumptuous flavors in downtown, which has a bustling restaurant scene. If you enjoy seafood, you will love crab dishes served at Doc's Sunset Grille. Finally, Tred Avon Players entertains vacationers with live theatrical performances.

Easton

This artsy community in Talbot County showcases its colorful identity through a rich mix of art galleries. Travelers come from far and wide to explore the town's vibrant art scene. Easton houses the Academy Art Museum, a regional hub famous for exhibiting beautiful art pieces and hosting engaging live performances in a 1900s building. Furthermore, the Troika Gallery focuses on fine art creations, displaying everything from oil to pastel paintings.

Those craving to uncover exciting local history will enjoy combing through Talbot County Historical Society exhibits. However, if you prefer to explore the outdoors, you can head to Idlewild Park and enjoy its relaxed atmosphere. It also offers amenities like picnic tables, a walking track, and a playground for the public's amusement.

Ocean City

This adorable beach resort community of Ocean City is the perfect spot for a family getaway. Although it only hosts around 7,000 permanent residents, it is always bustling with tourists seeking to take advantage of its fine weather and soothing beach scenery. The Ocean City Boardwalk is a popular corridor with a mix of restaurants, shops, and carnival rides, always teeming with family-friendly activities. The promenade is just next to Ocean City Beach, which provides a 10-mile stretch of sand ideal for sunbathing and strolling.

Several amusement parks along the picturesque shores, including Trimper Rides, promise unadulterated fun for all ages. The venues keep guests busy with thrill rides and a timeless carousel, among other fun pursuits.

Salisbury

Maryland's Eastern Shores conceals many gems, including this lovely locale in Wicomico County. Salisbury offers a little bit of everything to ensure all travelers have an excellent experience. It houses the Salisbury Zoological Park, which invites animal lovers to have inspiring encounters with cute native and exotic wildlife species. The Centre At Salisbury promises shopaholics delightful retail therapy opportunities across a sprawling regional mall with shopping stores, dining outlets, and entertainment centers.

Those who gravitate towards the open spaces will love the tranquil atmosphere of Schumaker Park, which has access to a scenic pond and a disc golf course. Lastly, the historically inclined will fancy touring Poplar Hill Mansion, a gorgeous restored home with a legacy stretching back to 1795.

Exploring these storied towns promises adventures around every scenic corner, from strolling historic streets lined with preserved architecture to sweeping vistas of the Chesapeake and its tributaries. Their charming downtown districts, nurtured for centuries, ensure a memorable cultural education and a glimpse into the state's enduring heritage. A trip to any of the highlighted towns to visit in Maryland culminates in a holistic experience, leaving a lasting impression that will have tourists returning for more.