St. Michaels, Maryland: Some of the shops and stores in St Michaels, MD along the town's main street. Editorial credit: George Sheldon / Shutterstock.com

9 Picture-Perfect Towns in Maryland

Despite its modest size on the East Coast, Maryland boasts scenic natural beauty, punctuated by diverse landscapes. While many tourists opt for big cities like Baltimore as a vacation destination, many are unaware that the lesser-known, rural locations are truly the heart and soul of the state. From picturesque coastal villages to quiet riverfront communities and hidden inland charmers, these small towns promise an experience like no other.

Collectively, these towns narrate Maryland's rich history from the Revolutionary War to the Civil War eras through captivating historical sites and landmarks. Each town has a distinct personality, hosting culturally-rich communities known for their trademark Southern hospitality. Furthermore, their lovely natural surroundings provide the perfect playground for all manner of outdoor adventures, ensuring there’s never a dull moment. With so many options to choose from, here are some of the most beautiful towns in Maryland.

Ocean City

The charming resort town of Ocean City, Maryland.
The charming resort town of Ocean City, Maryland.

As the name suggests, Ocean City charms first-timers with spectacular beach scenery. Boasting silky-smooth sandy shores, pristine beaches, and clear turquoise water views, the setting is ideal for a relaxed vacation. You can soak in the scenes along the vibrant Ocean City Boardwalk, which stretches three miles, housing restaurants, shops, bars, and other businesses. But if you prefer some alone time away from the crowds, you can head to Ocean City Beach, known for its more secluded atmosphere. This 10-mile stretch of pristine shoreline is perfect for sunbathing, relaxing, unwinding, and watching the sunsets.

Those craving some activity will fancy Northside Park, a 58-acre complex with a soccer field, baseball fields, playgrounds, and an indoor gym. Finally, art connoisseurs can visit the Art League of Ocean City to check out the local art scene. The facility showcases a range of artworks by local artists in its state-of-the-art gallery.

Chesapeake City

Shops and cafes on the water in Chesapeake City, Maryland.
Shops and cafes on the water in Chesapeake City, Maryland.

There is no shortage of beautiful coastal destinations in Maryland, and this Chesapeake Bay town is right among the top. Home to fewer than 1,000 people, Chesapeake City offers a tranquil escape from urban bustle, rewarding tourists with stunning water views and a variety of outdoor adventures. Boating excursions are a cultural staple in the town, and Chesapeake City Water Tours offer a chance to discover the area from the water. They offer fun sightseeing trips curated to customer satisfaction, complete with wine and craft beer tastings.

Chesapeake City boasts a rich maritime heritage, which you can explore at the C & D Canal Museum. The facility showcases the past and operation of the canal linking the Delaware and Chesapeake Bays, one of the most critical in the country. Enjoy an immersive historical experience on a stroll through the South Chesapeake City Historic District, which exudes 19th-century charm with its gorgeous old-world architecture.

Salisbury

Beach promenade in Salisbury, Maryland
Beach promenade in Salisbury, Maryland, via travelview / Shutterstock.com

Folk art harmoniously intertwines with unique history and charming outdoor pursuits in this small Eastern Shore town. Salisbury Zoological Park, ranked among the best small zoos in the country, is the ideal spot for a family outing. Though spanning only 12 acres, the park houses a range of exotic species from Australia, North, and South America. You'll be intrigued by the sloth, jaguar, and bear exhibits, offering rare opportunities for close encounters. At the 262-acre Pemberton Historical Park, uncover a historical gem while exploring lovely nature trails. The park features 4.5 miles of trails weaving through forested surroundings, along with a 1741 house museum that was once the home of Col. Isaac Handy.

More history awaits at the beautiful Poplar Hill Mansion, an 1805 manor house showcasing life in Salisbury during the Federal Period of American history. To complete your Salisbury experience, don't miss a visit to Morgan’s Oyster House to sample the local cuisine. This fine establishment serves some of the best seafood, featuring crab cakes, oysters, and shrimp.

Berlin

Historic downtown of Berlin, Maryland.
Historic downtown of Berlin, Maryland.

Berlin, a quaint community of about 5,000 in Worcester County, boasts one of the most vibrant Main Streets in any small town. Nearby, you'll find Assateague State Park, a popular recreation hub bordering the Atlantic Ocean. Tourists and locals alike gather here to enjoy sandy beaches, camping, and fishing opportunities, but the highlight is the migrating wild ponies that roam the coast. Berlin’s downtown is a charming mix of businesses, with seafood eateries, retail stores, museums, and bars giving the neighborhood an upbeat vibe.

The Mermaid Museum is one of the most interesting downtown venues to check out. This quirky attraction exhibits everything mermaid, with displays centered around the mythical creature. After a day of exploring, you can visit the Burley Oak Brewing Company to refresh with a glass of craft beer in a chill, rustic atmosphere.

Boonsboro

Historic buildings in downtown Boonsboro, Maryland
Historic buildings in downtown Boonsboro, Maryland

This charming town at the foothills of South Mountain is an adventurer’s paradise, offering an exciting mix of outdoor opportunities. Near Boonsboro is Greenbrier State Park, a public recreation epicenter with secluded hiking trails and camping sites. It also boasts a 42-acre artificial lake that attracts anglers, boaters, kayakers, and swimmers. Additionally, South Mountain State Park offers hikers an excellent opportunity to explore the area's wilderness. The park features almost 50 miles of primitive trails and a picturesque 80-foot waterfall.

In some areas, the park reaches altitudes of 3,000 feet, offering climbers sweeping views of the surrounding landscapes. For a family-friendly outing, Shafer Park is a great choice, with amenities like basketball courts, sports fields, and a kiddie park with play sets. For a change of pace, the Boonsborough Museum of History is a quaint indoor attraction chronicling the town’s storied past.

Havre De Grace

An empty street in Havre De Grace city at dusk.
An empty street in Havre De Grace city at dusk. Image credit Wirestock Creators via Shutterstock.

Named after the French port city Le Havre, Havre De Grace, located at the mouth of the Susquehanna River, impresses with its charming waterfront views, historical sites, and scenic trails. You can’t miss Concord Point Lighthouse when driving into the town. This iconic landmark, built in 1827 on the Chesapeake Bay shores, rises 36 feet high and serves as an ideal backdrop for photos, offering stunning views of the water. Millard Tydings Memorial Park is another cozy outdoor space of note.

The 22-acre park offers an easygoing atmosphere with plenty of shade, perfect for relaxing and unwinding. It also features an expansive pavilion where parents can relax while children play at the on-site playground. For history enthusiasts, a visit to the Havre de Grace Maritime Museum reveals the history of commercial crabbing and fishing in the area.

Thurmont

Corner of Main and Water in downtown Thurmont
Corner of Main and Water in downtown Thurmont, By Andrew Bain - Own work, CC BY-SA 3.0,File:Thurmont MD Corner of Main and Water.jpg - Wikimedia Commons

Thurmont’s town motto, “The Gateway to the Mountains,” preludes the type of adventure you can expect in this Frederick County community. One of the best towns in Maryland for outdoor adventurers, Thurmont is home to the rugged Catoctin Mountain Park. This more than 5,000-acre nature reserve provides hikers with 25 miles of trails and panoramic vistas of the Monocacy Valley. More outdoor opportunities await at Cunningham Falls State Park, home to the gorgeous Cunningham Falls.

In addition to viewing Maryland’s largest cascading waterfall, the park offers swimming, fishing, and kayaking on its 43-acre artificial lake. Animal lovers will enjoy the Catoctin Wildlife Preserve, a sanctuary for almost 1,000 beautiful animals. Here, you can have close encounters with exotic species, including the opportunity to pet and feed ostriches, llamas, and zebras.

Cambridge

The marina at Cambridge, Maryland.
The marina at Cambridge, Maryland.

Cambridge impresses with a blend of picturesque coastal scenery, rich maritime history, and enjoyable outdoor adventures. Long Wharf Park is a prime venue to take in the town’s natural beauty. This quiet riverside park offers an ideal atmosphere for unwinding, complete with facilities like picnic tables and bathrooms. While exploring the outdoors, make sure to visit the Choptank River Lighthouse, an iconic city landmark. Besides being a picturesque sight, the venue houses a small museum with engaging exhibits about the town’s nautical heritage.

There is more history to uncover at the Harriet Tubman Museum & Educational Center. Dedicated to honoring the legacy of the iconic figure Harriet Tubman, the center displays various artifacts and showcases videos that narrate the Underground Railroad, slavery, and Civil War periods. For indoor family fun, enjoy an entertaining faceoff at Choptank Bowling & Billiards.

St. Michaels

St. Michaels, Maryland: Traditional Store Decorated for Halloween on Talbot Street. St. Michaels is a picturesque harbor on Maryland's Eastern Shore.
St. Michaels, Maryland: Traditional Store Decorated for Halloween on Talbot Street. St. Michaels is a picturesque harbor on Maryland's Eastern Shore, Editorial credit: Albert Pego / Shutterstock.com

St. Michaels, a small community in Talbot County, offers a serene waterfront retreat. The town boasts a rich nautical heritage, which can be explored at the Chesapeake Bay Maritime Museum. With its vast collection of artifacts displayed in an 18-acre facility, it offers a comprehensive glimpse into the town’s maritime history. Car enthusiasts will fancy a tour of the Classic Motor Museum of St. Michaels, where a range of classic automobiles, motorcycles, and farm equipment is exhibited. Outdoor lovers can head to Muskrat Park to enjoy a peaceful natural setting by the water.

St. Michaels is renowned for its Chesapeake Bay cuisine. A visit isn’t complete without tasting local delicacies, and several tranquil downtown restaurants, including Ruse, offer these culinary experiences. After a wholesome meal, visit Eastern Shore Brewing for a refreshing glass of craft beer.

Final Thought

From unique American history and exciting coastal adventures to sumptuous Southern cuisine, the small towns in Maryland offer a range of attractions to keep you entertained throughout your stay. They embody the true charm of the Old Line State, and opting for these quaint towns over the big cities promises a unique and unforgettable experience.

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