8 Most Memorable Small Towns in Maryland

Beyond its bustling cities and sprawling suburbs, the Old Line State houses an array of tiny hamlets in its backcountry, offering an idea of the state’s diverse landscapes, captivating history, and rich culture. From small coastal fishing villages and picturesque mountain towns to hidden riverine communities, these unique localities deliver a quiet retreat, safe from the hustle and bustle in the urban centers.

They boast a tranquil setting surrounded by spectacular natural scenery, and each town delights with distinct historical heritage, unseen cultural traditions, and a charming mix of outdoor opportunities, promising an unforgettable vacation experience for all types of preferences. Whether planning your first tour of the state or making a return trip, here are some of the most memorable towns in Maryland to visit.

Chestertown

Chestertown lies along the scenic banks of the Chester River and charms with a rich history dating back to the 18th century. The Chestertown Historic District is listed on the National Register of Historic Places and stores a wealth of historic gems, featuring restored 18th-century homes with old-world architecture that currently house museums, shops, galleries, and restaurants. Strolling through the corridor feels like stepping back in time, but you can get a vivid glimpse into the town and surrounding region’s past at the Historical Society of Kent County. A series of artifacts, documents, and other memorabilia let you know Chestertown’s captivating history. 

There is an apparent acknowledgment and appreciation for the arts by the local community, evidenced by the various art venues dotting Chestertown. The Garfield Center for the Arts at the Prince Theater is an impressive facility that invites guests to enjoy live performances in a family-friendly atmosphere. However, outdoor enthusiasts will prefer hanging out at Wilmer Park. This charming nature space borders the beautiful Chester River and provides amenities like picnic tables, a pavilion, and a playground for the public’s amusement. 

Cambridge

A laidback waterfront village on Maryland’s Eastern Shore, the Cambridge community has a history of making a living from fishing and crabbing. It has tranquil coastal scenery and a Main Street ambiance that draws visitors from around and beyond. The Choptank River Lighthouse is an iconic town landmark to check out. Although it is a replica, the screw-pile construction is characteristic of lighthouses on the Chesapeake Bay that are rare to come by today. The landmark sits at the end of Long Wharf Park, a lovely outdoor space where you can enjoy a laid-back stroll along the Choptank River while taking in the water vistas. 

Cambridge downtown is replete with historical gems that will intrigue fans, highlighted by the Harriet Tubman Museum & Educational Center. This magnificent facility honors the legacy of Harriet Tubman by displaying historical artifacts and videos about landmark events like the Civil War, the Underground Railroad, and slavery. Finally, remember to sample iconic Chesapeake Bay cuisine at the different town restaurants, including the classy Blue Ruin. 

Emmitsburg

Home to Mount St. Mary’s University, this Frederick County town features a bubbly, youthful vibe and offers various outdoor adventures in the surrounding Catoctin Mountain. Emmitsburg has a rich Catholic heritage that you can get a feel of at its iconic landmarks. The National Shrine Grotto of Our Lady of Lourdes is among the most impressive, a gorgeous mountainside shrine replicating the famous Lourdes in France. Another cultural center to check out is the Frederick County Fire Rescue Museum, which preserves the local tradition of firefighting by exhibiting interesting historical artifacts. 

You can follow up this visit by paying tribute to the strong men and women who sacrificed their lives at the National Fallen Firefighters Memorial. Firefighting aside, Emmitsburg boasts a vibrant restaurant scene, with several joints serving sumptuous dishes to tickle your taste buds. While there is no shortage of options, Rube’s Crab Shack impresses with classic seafood like crab specials. 

Havre De Grace

Charming marinas, quaint museums, and a vibrant downtown scene draw tourists to this little locality at the mouth of the Susquehanna River. Havre de Grace was named after the French port city of Le Havre and is among one of the best Chesapeake Bay towns to explore. The Havre de Grace Maritime Museum preserves the region’s nautical heritage by exhibiting artifacts about local and commercial crabbing and fishing. But Havre de Grace is teeming with historical sights, and the Friends-Concord Point Lighthouse is a must-see for any buffs in town. The 36-foot landmark, built in 1827, is Maryland’s second-oldest lighthouse. 

For the outdoorsy traveler, the Millard Tydings Memorial Park offers 22 acres of natural oasis perfect for hanging out and relaxing. It has a peaceful pavilion and picnic areas where you can chill and enjoy sweeping views of the Susquehanna River. Alternatively, you can enjoy light exercise with a stroll along the Havre de Grace Promenade, a picturesque 3/4-mile boardwalk bordering the river.

Sykesville

Sykesville was once ranked as the “Coolest Small Town in America,” and a tour of this tiny Carroll County locality provides a feel of what makes it tick for travelers. Situated 30 miles from Baltimore, it offers a sweet escape from the busy city, rewarding tourists with relaxed outdoor scenery and quaint historical sites. If you fancy the open spaces, you can head to Millard Cooper Park to enjoy its quiet picnic areas, pavilions, and scenic nature trails. But if you are more inclined to historical pursuits, you can glimpse some of the town’s past at Historic Sykesville Colored Schoolhouse. The venue was opened in 1904 to serve as the only institution in Southern Carroll County for people of color. 

You'll want to visit the Gate House Museum for a broader look into Sykeville’s past. The facility harbors old stories, archives, and artifacts preserving the town’s history. After a day of touring the top sites, you can walk into the French Twist Café to savor luscious French cuisine and gourmet coffee. 

Williamsport

Williamsport has superb outdoor scenery punctuated with the Catoctin Mountain, making it one of the best towns in Maryland for nature lovers. Housing a tiny community of about 2,000 people, tourists can look forward to endless outdoor opportunities. At Byron Memorial Park, they will find a family-friendly nature space popular among locals for hosting car shows, picnics, concerts, and other public events. Alternatively, you can explore breathtaking natural scenery along the Williamsport C&O Canal. The route is perfect for walkers, bikers, and even hikers. 

Besides being a popular hiking spot, the canal is also a historical gem presenting a look into America’s primitive transportation history. You can learn more about this at the C & O Canal National Historical Park Headquarters, showcasing how it served communities along the Potomac River. Finally, you can wind up the day with a taste of refreshing craft beer at the Cushwa Brewing Company. 

Easton

Easton traces its history back to the early 1700s when it was founded, a rich heritage impressively preserved in its quaint historic homes and quiet downtown. There is a lot of history to explore in this Talbot County town, and you can start by browsing archives and artifacts at the Talbot Historical Society. But if you prefer cultural attractions, Easton has a charming mix of art centers that promise an immersive cultural experience. The Academy Art Museum is an excellent venue that welcomes visitors to explore exhibits, events, and classes that appreciate the arts on Maryland’s Eastern Shore. 

Meanwhile, remember to stop by Foxwell’s Antiques & Collectibles and hunt for a cute souvenir. The 10,000-square-foot establishment houses more than 60 antique dealers, ensuring there is something to impress everyone. Outdoor lovers will find a nice space to hang out at Idlewild Park, which has the perfect scenery for a family picnic. 

Annapolis

Despite being Maryland’s capital, Annapolis harbors a small community of just over 40,000, making it a worthy destination for those looking for a small-town escape. It is home to a treasure trove of historical sites that will take you to interesting moments in America’s past. The 1700s Maryland State House is a must-visit, considered the oldest state capitol in continuous legislative use. Another interesting venue you can’t miss out on is the Annapolis Maritime Museum & Park. This world-class waterfront facility focuses on the Chesapeake Bay region's maritime, ecological, and artistic history. 

Annapolis’ breathtaking outdoor scenery is evident when walking along the Annapolis City Dock. The vibrant corridor hosts a series of bars, restaurants, and shops with shaded areas where you can relax to take in the scenes. Meanwhile, one of the best experiences in the town awaits at the Pennsylvania Dutch Farmer’s Market, a great place to interact with the locals and sample authentic Dutch cuisine. 

From maritime heritage and captivating Civil War history to lovely downtown delights, the Old Line State excites visitors with a rich diversity of attractions. Unsurprisingly, it draws over 40 million annual visitors, who come to relax on its beautiful waterfronts, explore its interesting historic sites, sample its delectable culinary scene, and experience its unique culture. Whether a history buff, culture connoisseur, outdoor adventurer, or culinary enthusiast, these small towns in Maryland are a prelude to the magical experience awaiting in this beautiful Mid-Atlanftic state.