Top 15 Charming Small Towns in Maryland to Explore

Maryland, one of the original thirteen colonies, is a Mid-Atlantic state featuring beautiful coastlines along the Chesapeake Bay and Atlantic Ocean. Characterized by small towns situated both by the sea and across its expansive countryside, Maryland is rich in colonial history awaiting exploration.

Dedicate some time away from Baltimore and its urban attractions to experience the charm of small-town Maryland—at times you may feel as though you have traveled back in time to witness U.S. history first-hand! Visitors will enjoy both educational experiences and culinary delights, sampling the excellent food and drink offered by these towns or embarking on an exhilarating boat tour.

Here are our top recommendations for the best small towns to visit in Maryland:

1. Thurmont, Maryland

A quaint town in Frederick County, Thurmont is positioned in the northern part of Maryland, relatively close to the Pennsylvania border. Recognized as a “Main Street Maryland Community,” the town has diligently preserved its historic downtown, maintaining its charm and closeness to nature—its motto is “The Gateway to the Mountains.” This destination is particularly inviting for outdoor enthusiasts and art aficionados.

Thurmont hosts the annual Catoctin Colorfest, an arts festival that draws up to 125,000 attendees. Even if you cannot attend, make sure to visit Cunningham Falls State Park and Catoctin Mountain Park (the site of Camp David). Bring your hiking gear and explore the trails or opt for a leisurely stroll across Loy’s Station Covered Bridge. Additionally, acquire fresh fruit at Catoctin Mountain Orchard or enjoy wine tasting at Springfield Manor Winery and Distillery.

2. Berlin, Maryland

Contrary to what one might presume, we are not referring to the capital of Germany. Berlin, Maryland, located in Worcester County, takes its name not from German descent but is believed to derive from an old tavern known as Burleigh Inn that once resided here. This town has recently revitalized its downtown area and is recognized as a Maryland Mainstreet Community, making it a desirable destination for fishing and hunting enthusiasts.

Nearby attractions include Assateague State Park and Dr. Shred’s Surf Adventures for beachgoers. Capture moments along Main Street’s historic buildings and boutiques before enjoying a beverage at Burley Oak Brewing Company or Maryland Wine Bar. Savor delicious meals at The Blacksmith, followed by dessert at Bakes Dessert Cafe. Relax at Holland House Bed and Breakfast for a restful night.

3. Hampstead, Maryland

Situated in Carroll County, Hampstead was established when Robert Owings began constructing a road through the area. Initially called Spring Garden, it was later renamed Hampstead. Originally settled by the English, the town served as an agricultural center due to its fertile land. Today, this previously sleepy farming community has transformed into a modern town eagerly awaiting your exploration.

While visiting, consider horseback riding at Happy on Hooves, or if you prefer land activities, explore Prettyboy Reservoir Park or Leister Park. For a refreshing swim, drive to Cascade Lake. Experience local cuisine at A Town Bar and Grille, or indulge your sweet tooth at Snickerdoodles Bakery and Coffee House. Hilltop Hideaway Bed and Breakfast stands ready to offer you a tranquil retreat.

4. Crisfield, Maryland

Crisfield, located in Somerset County along Tangier Sound on Chesapeake Bay, began as a modest fishing village. It underwent a name change to Somers Cove before John Crisfield recognized the potential of exporting seafood and introduced the Pennsylvania Railroad to the town, which led to the current name and designation as the “Seafood Capital of the World” (with downtown reportedly built upon oyster shells!).

Although economic activity has diminished due to challenges facing the Chesapeake Bay, tourism thrives—encompassing events like the National Hard Crab Derby. Crisfield is also a prime departure point for visits to Smith Island and Tangier Island—consider renting a boat for exploration! Participate in the authentic crab and clambake at the J. Millard Tawes Crab and Clam Bake or the Scorchy Tawes Pro-Am Fishing Tournament. Moreover, take time to explore the pristine marshes at Janes Island State Park, filled with diverse marine and bird life.

5. Eastport, Maryland

An ideal retreat from urban noise, Eastport is just a bridge away from Annapolis. Nestled on a picturesque peninsula, Eastport embodies the relaxed atmosphere synonymous with small towns. Enjoy stunning views of Annapolis’ iconic landmarks—the State House and Naval Academy—while maintaining the tranquil ambiance of the town.

Experience dining along the waterfront at various restaurants; Carrol’s Creek Cafe comes highly recommended. For those enthusiastic about watersports, rent a kayak from Third and Severn for a day of aquatic adventure. Alternatively, explore land-based attractions such as the Maritime Museum. Occasionally, Eastport features outdoor concerts, oyster festivals, and even pirate ship excursions. Meanwhile, taste a crab pretzel from Davis’ Pub while savoring the fresh air.

6. Ocean City, Maryland

A renowned resort town located in Worcester County, Ocean City is a favored destination for tourists from the Mid-Atlantic region. The population swells during summer months as visitors flock to the coast for a quintessential beach getaway. The land upon which the town is established was originally owned by Thomas Fenwick, an English immigrant, and further developed in the late 1800s by Isaac Coffin to attract tourists, successfully ensuring that people continue to visit!

Indulge in a luxury experience at the Princess Royale Resort, where stunning waterfront views await. Dine with a view at the Hobbit Restaurant or Shark on the Harbor before enjoying drinks at Harborside Bar. Prepare your swimwear and head to Ocean City Beach and Boardwalk for sun-soaked fun, or rent a boat from Odyssea Watersports for a memorable experience on the water!

7. Havre de Grace, Maryland

Located at the meeting point of the Susquehanna River and Chesapeake Bay, Havre de Grace has a unique charm. Named after a town in France (Le Havre de Grace), this designation was established during the Revolutionary War following visits from Lafayette, who noted the town’s resemblance to the French seaport.

Visit this enchanting coastal community to discover what captivated Lafayette. Accommodations are available at the Spencer-Silver Mansion, particularly the charming carriage house. Stroll along the picturesque Havre de Grace Promenade or visit Concord Point Lighthouse. Engage in outdoor activities at Susquehanna State Park or enjoy a round of golf at Bulle Rock Golf Club. Conclude your day with a glass of wine at Mount Felix Vineyard & Winery.

8. Monkton, Maryland

Monkton is a serene country escape located in Baltimore County. This area is ideal for those seeking a tranquil rural getaway, characterized by expansive countryside, horse farms, and historic homes. Stop by as you pass through, and you will discover one of Maryland’s hidden treasures.

Horse enthusiasts may enjoy “My Lady’s Manor,” a beautiful expanse of land recognized for equestrian activity. Visit Ladew Topiary Gardens and take a break at Millstone Cellars for refreshments. Taste the delicious bison burgers at Gunpowder Bison & Trading Co for a perfect pit stop during your travels.

9. Oakland, Maryland

Positioned in the west-central region of Garrett County, Oakland is a former railroad town that boasts a well-preserved B&O railroad station where trains still run during special events.

If you possess an interest in trains, do visit the Oakland B&O station or lace up your walking shoes and head to Swallow Falls State Park. Explore horseback riding at Circle R Ranch, or play golf at Lodestone Golf Club. Venture onto the water with a rental from Brill’s Marine Service, and unwind afterward at the Will O’ the Wisp hotel—a perfect escape immersed in nature that will leave you wanting more.

10. St Mary’s City, Maryland

St Mary’s City is the first colonial settlement in Maryland and was the site of the founding of the Maryland Colony, making it the fourth oldest permanent English settlement in the United States. Furthermore, it was the first location in the U.S. to establish a refuge for both Catholics and Protestants. This destination offers a unique experience for history enthusiasts who can experience history interactively.

Visitors can explore the reconstructed original colonial settlement and engage with living history museums featuring staff dressed in period attire recreating historical events. Additionally, the site includes a functioning colonial farm and a replica of The Dove Sailing Ship, one of the original vessels that brought settlers to Maryland. Discovering history has never been more engaging!

11. New Market, Maryland

New Market, located in Frederick County, is distinguished as the “Antiques Capital of Maryland.” The town was founded following the establishment of trade routes between Frederick and Baltimore, quickly emerging as a vital stop along these paths, and continues to attract visitors today.

Explore the vibrant downtown area and visit quaint shops specializing in antiques and various goods. New Market hosts two annual festivals celebrating its heritage: “Christmas in New Market” in December and “A Day in New Market” in May, honoring traditional 18th and 19th-century life. Whether or not you attend the festivals, indulge in a meal at Vintage or spend the night at Strawberry Inn B&B.

12. Vienna, Maryland

Located in Dorchester County, Vienna is not named after Austrians as one might assume, but was instead first encountered by the English when Captain John Smith met the Nanticoke Indians during his explorations. Set along the Nanticoke River and surrounded by verdant surroundings, Vienna offers ample outdoor activities.

When not exploring the riverside or taking a canoe out, visit Layton’s Chance Vineyard and Winery for a few delightful glasses of wine. Consider staying at the serene Tavern House, perfectly situated on the water for breathtaking views. Take in the sunset from the River Pavilion or along the Waterfront South and escape the hustle of urban life.

13. Emmitsburg, Maryland

Located in Frederick County, Emmitsburg lies south of the Mason-Dixon Line that separates Maryland from Pennsylvania. This town serves as a pilgrimage site for Catholics, being home to both the National Shrine Grotto of Our Lady of Lourdes and the Basilica and National Shrine of St. Elizabeth Ann Seton (the first natural-born U.S. citizen canonized as a saint). Regardless of religious affiliation, the town features panoramic views and historic structures worth exploring.

Spend time at the Mason Dixon Welcome Center or visit the historic Mount St. Mary’s University. Explore the pilgrimage sites or the Emmitsburg Antique Mall. Indulge in a drink at the Ott House Pub before enjoying dinner at the Carriage House Inn, where you may also find comfortable overnight accommodations.

14. Leonardtown, Maryland

As the county seat of St. Mary’s County, Leonardtown is a paradise for seafood enthusiasts. The town has engaged in revitalization efforts within its downtown area, establishing new businesses in historic buildings and introducing Leonardtown Wharf. Pay a visit for shopping or, if you’re fond of watersports, you will find many options.

Stroll and shop at the Wharf or meander along the waterfront to take in the views. Boat, kayak, or canoe rentals are available for those interested, while others may choose to further explore the historic downtown. Sites like Tudor Hall and St. Andrew’s Church, both listed on the National Register of Historic Places, should not be missed. Conclude the day with refreshments at Fitzies Marina Restaurant and Pub, or spend the night at the Executive Inn.

15. St. Michaels, Maryland

Situated in Talbot County, St. Michaels derives its name from the Episcopal Parish established in 1677, predating the town itself, which was established in the 1700s. St. Michaels flourished as settlers arrived to embark on business ventures, shipbuilding, or tobacco cultivation. It also served as the battlefield in the War of 1812, where it was targeted by the British due to a militia battery. Local legend states that the town avoided destruction from cannon fire by hanging lanterns in trees, hence becoming known as the town that “fooled the British.”

Today, visitors can still observe the Cannonball House, a structure that reportedly endured a direct hit. Explore the historic district and its charming center, or visit the Episcopal Church located off the primary route. Spend time at the Chesapeake Bay Maritime Museum to learn about the town’s unique boat designs or enjoy fresh seafood at St. Michaels Crab & Steak House. This delightful seaside town will surely captivate you, inviting you to extend your stay.