Aerial sunset panorama of Havre de Grace, Maryland, featuring an orange sky and clouds reflecting on the Susquehanna River and the Chesapeake Bay. One of America's best small towns.

7 Cozy Towns to Visit in Maryland

Bordered by the District of Columbia and the neighboring US states of Pennsylvania, Delaware, Virginia, and West Virginia, Maryland is a stunning Mid-Atlantic state with an attractive coastline along the vast Atlantic Ocean and the Chesapeake Bay. However, the tiny size of the state inadvertently conceals its varied topography, ranging from the low-lying hydrophilic Eastern Shore to the West’s forested Appalachian panoramas, which have rightfully earned Maryland the nickname “America In Miniature.”

While ‘The Old Line State’ is widely known for urban metropolises like Baltimore, Annapolis, and Germantown, the innumerable cozy towns that dot the state’s 9,776 sq. mi terrain are waiting to be explored. Spare time from your busy schedules and make plans to tour these Maryland towns on the next short weekend or long vacation trips.


Downtown Thurmont, Maryland: Intersection of Main and Water Streets, facing north on Water Street.
Downtown Thurmont, Maryland: Intersection of Main and Water Streets. By Andrew Bain, CC BY-SA 3.0, Wikimedia Commons

Home to 6,935 residents, Thurmont is a teeny Frederick County town along U.S. Route 15 that lies at the base of Catoctin Mountain - the easternmost mountain ridge of the Blue Ridge Mountains, approx. 10 miles from the state border with Pennsylvania. The town’s proximity to the Catoctin Mountain Park, with its pretty hiking and camping areas, has made it a favorite destination for adrenaline junkies. The town also houses “Camp David” - the Presidential retreat and the Cunningham Falls State Park featuring Maryland’s highest cascading waterfall and a 43-acre artificial lake that offers myriad water-based recreations.

Furthermore, Thurmont has many old covered bridges, the Thurmont Trolley Trail, Catoctin Mountain Orchard, a strollable Main Street, Catoctin Wildlife Preserve & Zoo, and the Catoctin Breeze Vineyard. Considered one of the biggest outdoor arts & crafts festivals on the East Coast, the Catoctin Colorfest, held annually on the second weekend of October, draws more than 125,000 merrymakers.


Berlin, Maryland: Historic downtown with old brick buildings, narrow streets, and small tourist shops.
Berlin, Maryland: Historic downtown. Editorial credit: Kosoff /

Promoted as “America’s Coolest Small Town,” Berlin, roughly 10 miles inland from Assateague Island National Seashore and Ocean City, forms a part of the Salisbury, MD-DE Metropolitan Statistical Area. Christened after the antique tavern ‘Burley Inn,’ this Worcester County town is acclaimed for dozens of well-preserved late-19th-century properties in different architectural styles that line the streets of the downtown commercial district and abutting residential areas. History enthusiasts must tour the Merry Sherwood Plantation House, Calvin B. Taylor House Museum, Burley Manor, Henry’s Grove, and Mermaid Museum, while the unspoiled landscape of Assateague State Park - Maryland’s sole oceanfront park entices all nature lovers.

Do not forget to browse the plethora of art galleries, trendy shops, premier eateries, and breweries like Burley Oak Brewing Company and Rayne’s Reef Soda Fountain & Grill in Berlin’s charming downtown. The town hosts Oktoberfest, the Berlin Christmas Parade, the Berlin Spring Cruisers Classic Car Show, the Berlin Farmers Market, the 2nd Friday Art Stroll, and Berlin Bathtub Races every year.

Saint Michaels

St. Michaels Harbor in historic Saint Michaels, Maryland, during spring. The town's name originates from a local Episcopal parish established in 1677, popular among tobacco growers and shipbuilders.
St. Michaels Harbor in historic Saint Michaels, Maryland.

Aptly labeled “The Heart & Soul of the Chesapeake Bay,” Saint Michaels is a quaint Talbot County town along the Miles River on the state’s Eastern Shore. This adorable waterfront getaway just an hour and a half drive away from Washington D.C. holds on to its appearance as a 19th-century seaport gladly upholding the moniker ‘the town that fooled the British.’ Saint Michaels’s walkable downtown is overflowing with countless Victorian-era properties that at present house stylish boutiques, one-of-a-kind shops, and superb bed & breakfasts.

When in town, the Chesapeake Bay Maritime Museum, St. Michael’s Museum, 1879 Hooper Strait Lighthouse, Classic Motor Museum, Saint Michaels Mill, and A. M. Gravely Gallery are must-visits. Also, satiate your taste buds at high-quality restaurants such as The Crab Claw, Limoncello Italian Restaurant & Wine Bar, and Ava’s Pizzeria & Wine Bar.

Bel Air

Bel Air Mansion, Maryland, USA: A historic landmark.
Bel Air Mansion, Maryland, US: A historic landmark.

Harford County’s administrative center, Bel Air, is in Northeast Maryland, around 30 miles north of Downtown Baltimore. Planned on a part called “Scott’s Old Fields” of an inherited land by Aquilla Scott, this laid-back community and its adjacent suburbs have considerably grown over the years, transforming Bel Air into the county’s leading governmental, commercial, medical, cultural, and educational hub. Discover prominent attractions like the Bell Air Armory, Tudor Hall, Harford Mall, Liriodendron Mansion, etc., while hiking along the Ma and Pa Trail.

The Bel Air Arts and Entertainment District, which encompasses a major portion of Bel Air’s Downtown, is primarily used for concerts, theaters, festivals, dance performances, and different yearly cultural celebrations. Rockfield Park - the town’s sole community park, together with five neighborhood parks, provides multiple recreation amenities such as play equipment, horticultural gardens, an extensive trail network, picnic facilities, and an amphitheater that supports an active summer concert series.


Emmitsburg, Maryland, USA: View of the town square looking northeast.
The town square in Emmitsburg, Maryland. By Acroterion, CC BY-SA 3.0, Wikimedia Commons

This Frederick County town, named in honor of William Emmit - the local landowner, is roughly 0.3 miles south of Mason-Dixon Line. Emmitsburg is home to the main 1,400-acre campus of Mount St. Mary’s University (“The Mount”), apart from other notable sites of interest including the National Shrine Grotto of Lourdes, National Fallen Firefighters Memorial, National Shrine of Saint Elizabeth Ann Seton, and Emmitsburg Antique Mall. Additionally, drop at Emmitsburg’s first-class restaurants, such as Carriage House Inn Restaurant, Chubby’s Barbeque, Ott House Pub, etc., that serve delectable crab dishes as well as Italian foods and Southern-style cuisines.

Mount Airy

Downtown Mt Airy, Maryland, USA.
Downtown Mt Airy, Maryland, US. By R london, CC BY-SA 3.0, Wikimedia Commons

Mount Airy, occupying the boundary between Carroll and Frederick counties, forms a part of both the Washington Metropolitan Area and the Baltimore-Columbia-Towson Metropolitan Statistical Area. Originally founded along the Baltimore & Ohio Railroad line in 1830, the town's official name was proposed by an Irish B&O worker, who complained about his freezing ears during a windy workday due to the chilly winds blowing across the railroad station at Parr’s Ridge.

Mount Airy’s Main Street is chock-a-full of late 19th or early 20th-century landmark properties, aside from scores of boutique shops, cafes, parks, galleries, eateries, farms such as the Knill’s Farm Market, and breweries and independent wineries like Stillpoint Farm’s Milkhouse Brewery, and Black Ankle Vineyards.

Havre de Grace

Aerial sunset panorama of Havre De Grace, Harford County, Maryland, featuring the railroad bridge over the mouth of the Susquehanna River and the head of Chesapeake Bay. One of America's best small towns.
Aerial sunset panorama of Havre De Grace, Harford County, Maryland.

A picture-perfect Harford County hamlet, Havre de Grace, dubbed after an important French port city, is set at the meeting point of the Chesapeake Bay and the Susquehanna River, about 40 miles northeast of Baltimore. A coveted recreation and tourism haven, this enchanting community is celebrated for its beautiful bayfront views, marinas, elegant Victorian properties in the Havre de Grace Historic District, the renovated Havre de Grace Promenade & Boardwalk, and impressive museums like the Havre de Grace Maritime Museum, Decoy Museum, Lockhouse Museum, and Concord Point Lighthouse. The Susquehanna State Park and Millard Tydings Memorial Park offer picnicking, bird watching, fishing, horseback riding, camping, and boating activities amidst incredible surroundings.

Discover the Heart of Maryland's Cozy Towns

From Saint Michaels - “The Heart & Soul of the Chesapeake Bay” to the postcard-pretty Havre de Grace, the teeny communities in the nation’s 9th smallest and 18th most-populous state enthrall holidayers with their authentic charms. Boasting magnificent coastal settings, fascinating colonial heritage, thriving community spirit, eateries serving appetizing cuisines, and a welcoming ambiance, these small towns perfectly epitomize the true essence of the “Free State.” Whether you wish to indulge in some boutique shopping, witness ample historic architecture, peruse a treasure trove of museums, and delight in the great outdoors, these home-like towns are worth touring for memorable experiences.

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