
8 Most Breathtaking Towns In Maryland
The scenic state of Maryland wraps around the Chesapeake Bay, split by the iconic waterway into the Eastern and Western shores. This is a major aspect of its idyllic natural beauty, which also includes the rugged Appalachian Mountains on the western edge of the state. The Old Line State is also celebrated for its fascinating historical heritage, being one of the original thirteen states. But beyond its rich colonial past and famed blue crab feasts lies an array of little towns that are nothing short of breathtaking.
From coastal hamlets with working harbors to mountain hideaways surrounded by rugged wildernesses and vibrant suburbs lined with postcard-perfect main streets, Maryland’s small towns capture the state’s essence in full color. Each brings a unique feel to the table, whether you want to explore the outdoors, indulge in the arts scenes, or admire centuries-old architecture. From Ocean City to Thurmont, these breathtaking towns in Maryland deserve a spot on your travel list.
Ocean City

Ocean City lures tourists with its cozy tropical temperatures, sand-swept beaches, and soothing vistas of the Atlantic Ocean. This waterfront paradise guarantees fun moments for the whole family, thanks to its amusement parks. The Jolly Roger Amusement Park is one-stop for all things entertainment, offering a Ferris wheel, roller coasters, water slides, mini golf, go karts, and more. A short walk from the site brings you to the Ocean City Boardwalk, a historic corridor with an eclectic blend of shops, vendors, pubs, and restaurants.

Meanwhile, those who want to hit the beach can access a 10-mile shoreline at Ocean City Beach for a refreshing dip or a nonchalant walk while lost in the vast water views. Ocean City is also known for its numerous annual events, from Oceans Calling Festival to Ocean City Film Festival, hence it's never a dull time in the area.
Berlin

Many travelers consider Berlin to be one of the most enchanting destinations in the state, with unique charm centered between its well-preserved downtown district and relaxed countryside with breathtaking natural spaces. The Berlin Commercial District harbors a vibrant mix of museums, galleries, bars, restaurants, and other local businesses. A tour of the Calvin B. Taylor House takes guests back to the 1800s with elaborate antiques and memorabilia. Meanwhile, hundreds of local growers and crafters grace the Berlin Farmers Market as they display their assorted items for visitors to buy.

Downtown also invites newcomers to indulge in its brewery scene at Burley Oak Taproom & Brewing Company. But beyond the neighborhood, Berlin impresses visitors with heavenly natural scenery at Assateague State Park. This oceanfront oasis features a secluded ecosystem of beaches, marshlands, and maritime forests, with a distinct population of free-roaming wild ponies.
Thurmont

Thurmont is an excellent destination in northern Maryland, about ten minutes from the Pennsylvania border. Tucked away in the foothills of the Catoctin Mountains, it is a dream come true for ardent outdoorsmen and exposes them to rugged climbing trails at Catoctin Mountain Park. The 5,000-acre reserve remains a recreation hub throughout the year, offering rock climbing, camping, fishing, and fly-fishing opportunities. Cunningham Falls State Park captures the beauty of Thurmont's outdoor scenery, highlighted by Maryland's highest waterfall. The 78-foot wonder tumbles into a natural pool when guests and locals alike go to swim.
Animal lovers can interact with beautiful animals at the Catoctin Wildlife Preserve, whose 100-acre property provides a sanctuary for over 300 species. Thurmont also boasts an enduring heritage dating back to the mid-18th century, which tourists can explore by scouring through piles of artifacts at the Thurmont Historical Society.
Cumberland

Cumberland is a jewel in Western Maryland, set in the picturesque foothills of the Allegheny Mountains. It offers a charming blend of storybook outdoor landscapes and a historic downtown district laden with museums, galleries, boutiques, and restaurants. According to the Allegany Museum, the town was settled in the early 1700s, and its long backstory is brought to life using a library of over 50,000 items. The Gordon-Roberts House offers a glimpse into the past with a well-furnished dwelling depicting life in the Victorian era.
Beer lovers will fancy sampling delicious local offerings at the historic taproom of 1812 Brewery. But if you are concerned about Cumberland's impressive nature, a ride on the Western Maryland Scenic Railroad promises a rare sightseeing opportunity as it chugs through forested mountains in its backcountry.
Oakland

Oakland is one of the most underrated small towns in Maryland and impresses visitors with its pristine natural landscapes, marked by lush forests, imposing mountains, and vast lake waters. The town beckons hikers and expeditioners to step outside and discover the unmatched beauty of Swallow Falls State Park. This breathtaking reserve, traversed by the Youghiogheny River, is home to Muddy Creek Falls, centuries-old hemlocks and pines, and dozens of campsites. Meanwhile, the sprawling Herrington Manor State Park welcomes guests for some fun on the water, featuring fishing, swimming, and kayaking at Herrington Lake.
Beyond the outdoors, Oakland's rich history shines at the Oakland B & O Railroad Museum, which chronicles local railway heritage inside a 19th-century Queen Anne-style depot. Also, you can check out the whimsical exhibits at the Garrett County Museum of Transportation, ranging from historic carriages, buggies, and automobiles to sleighs.
Chestertown

Chestertown is a colonial village on the banks of the Chester River, known for its site-rich historic downtown district, where a vibrant art scene and enduring heritage collide. The busy corridor is home to the Garfield Center for the Arts, which supports local arts and artists by staging year-round performances and exhibitions. History buffs can take a step back in time to explore Chestertown's enthralling backstory at the Historical Society of Kent County. This stockpiles artifacts, documents, memorabilia, and relics about the town since its early 1700s establishment.
The Chestertown Farmers Market offers newcomers the opportunity to understand the character and culture of the area through hands-on interactions with friendly and welcoming vendors. Finally, those wishing for a change of scenery can opt for an easygoing cruise down the river courtesy of the Chester River Packet Company.
Salisbury

This delightful waterfront community on Maryland's Eastern Shore charms guests with its broad spectrum of attractions, which guarantees a fun experience regardless of your preferences. Salisbury calls on animal lovers to show genuine TLC at Salisbury Zoological Park, which provides a refuge for native and exotic reptile, bird, and mammal species from around the globe. Historians and environmentalists will find mutual interest in Pemberton Historical Park. The 260-acre property houses Pemberton Hall, an 18th-century plantation house surrounded by wooded trails, scenic picnic areas, and pristine wetlands.
The Poplar Hill Mansion is another must-visit historical marker providing a vivid portrayal of the early 1700s with its unique Federal-style architecture and elaborate period furnishings. Lastly, Shoppers and foodies can look forward to a modern experience at the Center At Salisbury, which accommodates dozens of brand-name stores, restaurants, and entertainment venues.
Monkton

This unassuming rural village in northern Baltimore County offers a nice break from city life with its relaxed atmosphere and rich natural scenery. Monkton's scenic beauty is epitomized by the Ladew Topiary Gardens, which boast 250 acres of pristine topiary farms and formal gardens, perfect for exploring on foot. Art lovers and artists often gather inside Manor Mill to indulge in their favorite pastimes. This cultural hub houses a mix of art gallery, live performance stage, woodworking station, and meditation center, connecting the public with the arts.
Elsewhere, those with a penchant for delicious local brews can take a tour of Inverness Brewing. This 100-acre farm has thriving hop plants, seasonal crops, and black Angus cattle grazing in the area. Its on-site brewery crafts flavorful beers from locally sourced ingredients.
The small towns in Maryland are a rich tapestry of natural beauty, historical heritage, and cultural splendor that expose tourists to different sides of the Old Line State. Unlike the constant chaos in the city, these hidden gems allow you to slow down and let your guard down as you explore quaint downtown districts, secluded outdoor treasures, and enduring local traditions. From Oakland's wonderful wilderness to Berlin's vibrant Main Street, each destination is a jewel waiting to be discovered in the United States.