14 Prettiest Small Towns In Maryland
According to the Tourism Office of Maryland, approximately 45 million tourists streamed into the state in 2023. This underscores its position among the top destinations in the South, and tourists can look forward to exciting experiences. Spread across the Old Line State, from the shores of the Atlantic to the foothills of the Blue Ridge Mountains, are adorable little towns that epitomize the state's true heart and soul.
Through them, guests discover hidden historical heritage, authentic cultural practices, and diverse natural beauty synonymous with this delightful state. Whether planning a weekend trip alone or a month-long vacation with family, these prettiest small towns in Maryland should be on your next travel itinerary.
Chesapeake City
Set along the picturesque Chesapeake Bay shoreline, Chesapeake City is a quintessential small-town escape for tourists who appreciate a sense of privacy. The sprawling waters surrounding the town invite exciting excursions at sea courtesy of Chesapeake Water Tours. This easygoing cruise is curated to your ultimate enjoyment, offering themed sunset cruises and wine-tasting tours. Away from the water, Pell Gardens Park allows outdoorsy guests to revel in a soothing breeze from the water in a tranquil green space while admiring passing vessels.
Chesapeake City's rich history comes alive at the Chesapeake City Historic District, which harbors a cluster of 19th and 20th-century buildings. You can learn more about the town's past at the Chesapeake City Museum, home to thousands of newspapers, manuscripts, photographs, and other relevant artifacts from the community.
Boonsboro
Boonsboro is an adorable community at the base of South Mountain, steeped in natural beauty and historical heritage. Adventurers are drawn to its multiple outdoor opportunities, abundantly available across Greenbrier State Park. This lovely wilderness provides access to a 42-acre reservoir that supports boating, swimming, canoeing, and picnicking activities. The iconic Appalachian Trail is another reason to visit Boonsboro, accessible inside South Mountain State Park. Hiking the route exposes you to sweeping panoramas at several vantage points, including Weverton Cliffs and High Rock.
Boonsboro's dynamic history intertwines with the Civil War, which is well documented inside the Boonsborough Museum of History. The venue stockpiles a vast collection of weapons, arrowheads, glassware, ceramics, and other memorabilia.
Monkton
This beautiful borough is just half an hour outside of Baltimore, and a great escape from the bustle of the city. It boasts storybook green spaces, best exemplified by the Ladew Topiary Gardens. This 22-acre sanctuary displays award-winning gardens lined with topiaries and harbors a scenic nature walk designed for lazy strollers. For art lovers, Manor Mill displays beautiful creations in a pre-Revolutionary grist mill with an art gallery, music performance center, and a yoga station.
Monkton also welcomes visitors to sample delicious craft beers at Inverness Brewing, served alongside delicious farm-to-table dishes. The establishment sits on a 100-acre farm and presents exciting panoramas of the surroundings.
Ocean City
Ocean City offers an alluring combination of sun, sand, and sea in a serene coastal location that draws thousands of summer vacationers. The atmosphere compels guests to let their hair down with access to the sandy shoreline of the Atlantic Ocean. This includes the 10-mile stretch of sand at Ocean City Beach, perfect for sunbathing and swimming in the turquoise ocean waters. The beach is next to the Ocean City Boardwalk, a vibrant corridor with shops, boutiques, restaurants, and other family-owned businesses.
Ocean City's abundance of amusement parks makes it an excellent destination for family outings. You can choose between Jolly Roger Amusement Park and Trimper Rides of Ocean City to take the kids for fun.
Bel Air
Bel Air is a lovely community in Harford County with a blend of pleasant history, natural allure, and an eclectic culinary scene. Despite its small size, the town houses a cluster of nearly 50 restaurants serving local and internationally inspired flavors. Mucho Gusto Bel Air is known for its sumptuous Mexican cuisine, ranging from chicken tacos and churros to guacamole. Meanwhile, history buffs will relish a tour of Liriodendron Mansion, which was built in the 1890s and provides a window into the past.
Those looking for open spaces can visit Bynum Run Park. This serene nature area features a loop trail straddling a pristine pond and benches where you can sit and meditate or enjoy a read.
Westminster
This charming Carroll County municipality is known for its broad spectrum of attractions, touching on history, nature, the arts, and entertainment. Westminster is home to the Carroll County Farm Museum, a 15-building complex featuring a tin shop, barn, and general store, portraying life in the 1800s. A rich network of nature spaces encourages newcomers to step outside, granting them access to the 320-acre Bear Branch Nature Center. The park hosts 5 miles of trails looping around the picturesque shores of Lake Hashawha.
Elsewhere, the Carroll County Arts Council supports and promotes the local arts community through art exhibitions, live art performances, and events. It also hosts classes and workshops for anyone looking to improve their technique.
Berlin
Berlin balances a lively downtown district with exquisite outdoor scenery to guarantee tourists the best of both worlds. There is no shortage of attractions in the urban core, and visitors can start by inspecting local history at the Calvin B. Taylor House. This Federal-style home was built in the 1830s and maintains original artifacts and furnishings, providing a feel for the Victorian era. Meanwhile, the Mermaid Museum intrigues first-timers with an unusual collection of exhibits related to mermaids.
A trip to Assateague State Park provides the perfect escape from the downtown crowds. This heavenly island escape offers a mix of sandy beaches, a fishing pier, and boat ramps. It is also known for the wild ponies that roam the grassy shoreline nonchalantly.
Cumberland
Cumberland is a scenic gem in Western Maryland framed by picturesque views of the Allegheny Mountains. The beautiful outdoor scenery compels guests to ride the Western Maryland Scenic Railroad, which winds through an isolated wilderness with a dense forest. The vintage train trip is best taken during fall as the leaf color changes, transforming the area into a kaleidoscope of colors. Cumberland's rich story shows in different historical markers, including the Gordon-Roberts House from 1867. The home stores toys, furnishings, art, and other memorabilia from the Victorian times.
Visitors interested in the arts can join local enthusiasts at the Cumberland Theatre to watch exquisite stage performances. This renowned cultural hub is a staple for plays, dramas, musicals, and other live shows.
Leonardtown
Leonardtown is a friendly riverfront community in St. Mary's County with breathtaking waterways and a pedestrian-friendly downtown district. The town square hosts a fair share of historical markers that offer an idea of the local heritage. Prominent among them is the Old Jail Museum & Leonardtown Visitor Center, a 19th-century sheriff's station with artifacts from the period. Guests can enjoy a fun shopping experience at Shepherd's Old Field Market, where over 90 locally-owned businesses sell everything from clothing and home decor to antiques.
Outdoor lovers find themselves gravitating toward Leonardtown Wharf Park. This waterfront oasis offers a quiet escape where you can sit back and soak up majestic vistas of the Potomac River. It is ideal for picnics, lazy walks, and kayaking excursions.
Havre De Grace
Havre de Grace is surrounded by the beautiful waters of the Chesapeake Bay and the Susquehanna River, considered among the prettiest small towns in Maryland. Its relaxing vibe is thanks to the rich natural surroundings, which visitors can soak in from the Havre de Grace Promenade. This pleasant walkway is perfect for anyone craving a quiet walk to interpret. The imposing facade of the Friends-Concord Point Lighthouse underscores the area's maritime heritage. It was erected in 1827 and hosts educational tours exposing rare historical heritage.
However, the Havre de Grace Maritime Museum offers more to learn about the community's nautical history. The facility documents several stories about the region's crabbing, oystering, and fishing exploits.
Chestertown
A mix of thriving cultural scene and beautiful heritage attracts visitors to this delightful riverside community. Chestertown lies on the banks of the Chester River and boasts a collection of galleries and art centers. The Chestertown Arts and Entertainment District is home to sites like the Garfield Center for the Arts, which supports local performers by staging live shows. It is also home to the MassoniArt Gallery, where small-time and big-name artists showcase their creations.
Those curious about Chestertown's past can find all the relevant resources at the Historical Society of Kent County. The center harbors piles of artifacts and archives, documenting the chronology of the community since its 1700s establishment.
Lexington Park
Lexington Park's colorful original is directly linked with the establishment of the Patuxent Naval Air Station during the Second World War. It is home to the Patuxent River Naval Air Museum, which preserves the area's naval heritage through a collection of aircraft artifacts. The town spoils outdoor lovers with a fine selection of options. You can head to John G. Lancaster Park for an easygoing picnic amidst nature or escape to the sandy shores of Elm's Beach Park for some alone time.
Meanwhile, art enthusiasts and aspiring actors can seek inspiration at the Newtowne Players. This modest community performance venue invites tourists to watch compelling live shows by homegrown talent, featuring dramas, concerts, and musicals.
St. Michaels
Small-town charm meets coastal allure in this adorable village on the Chesapeake Bay shoreline. St. Michaels is a popular summer getaway for private tourists and treats them to easygoing tours on the water aboard the St. Michaels Harbor Shuttle. This scenic cruise explores the town's waterways, offering a unique perspective of its beauty. The Chesapeake Bay Maritime Museum is an excellent stop for historians, who learn about the region's unmatched maritime history by browsing loads of memorabilia dating back to the 19th century.
St. Michaels' Chesapeake Bay cuisine entices food enthusiasts with sumptuous seafood dishes at Bistro St. Michaels, featuring crab and oyster specials. Later, you can stop by the St. Michaels Winery to sample some of the tastiest wines on Maryland's Eastern Shore.
Thurmont
Thurmont is a popular getaway to the Catoctin Mountains and a haven for ardent outdoorsmen. It promises endless adventures across its picturesque wilderness area, with admirers coming to witness Maryland's highest waterfall at Cunningham Falls State Park. While the 78-foot waterfall is the highlight of the park, it offers opportunities for hikers, campers, and boaters on a 43-acre reservoir. Additionally, the Catoctin Mountain Park spoils adventurers with 5,000 acres of rugged territory to explore.
The reserve lets you indulge in numerous activities, including rock climbing, fly fishing, camping, and hiking. Finally, make the most of rare wildlife encounters at the Catoctin Wildlife Preserve. This modest sanctuary boasts about 300 animal species, including zebras, meerkats, and monkeys.
Whether it's your first time in the Old Line State or you have been visiting it for years, some destinations tend to leave a lasting impression on visitors. Thanks to their captivating backstories, absorbing cultures, enchanting natural beauty, and receptive residents, they keep you coming back for more experiences. From the beachside charm of Ocean City to the artsy flair in Chestertown, the prettiest small towns in Maryland truly showcase the diversity that draws millions of annual visitors to the state.
