12 Unforgettable Small Towns to Visit in Maryland
Maryland, one of the original thirteen colonies, is a state steeped in American history that promises unforgettable towns worth visiting. Founded in 1634, Maryland hosts a treasure trove of historical landmarks that take visitors back to the colonial era. But Maryland offers more than just nostalgia, and exploring its charming small towns gives exposure to the many unique sides of the Old Line State. From experiencing diverse cultural heritage, admiring sweeping coastal views, relaxing in lush state parks, and sampling Maryland’s famous seafood scene, these small destinations promise a remarkable experience filled with lifetime memories.
Havre De Grace
This quaint little locale sits where the Chesapeake Bay meets the Susquehanna River, impressing with picturesque waterfront views. It was named after the French port city, Le Havre, and hosts a population of about 15,000 residents. One of the top activities in the town is strolling along the ¾-mile Havre De Grace boardwalk, which encompasses scenic vistas of the Susquehanna River. The promenade is also close to several of the area’s top attractions, including the Decoy Museum and Maritime Museum, where you can glimpse Havre De Grace’s storied past.
The highlight of your experience will be a tour of the Friends-Concord Point Lighthouse, an iconic town landmark built in the 1820s. The 36-foot lighthouse attracts a huge crowd and is free to visit. For a great view, visitors can climb to the top and check out the Keeper’s House or take in the unprecedented scenery of the Chesapeake Bay and Susquehanna River. Not too far away is Millard Tydings Memorial Park, a delightful nature spot excellent for picnicking or relaxing by the water.
St. Michaels
This charismatic harbor town offers a unique blend of attractions that are relished in discovering. With a modest population of just over 1,000, St. Michael’s is one of the best coastal getaways in Maryland. Its stunning backdrop was featured in the famous Hollywood flick Wedding Crashers. At the Chesapeake Bay Maritime Museum, you can browse through a lovely collection of artifacts, sea vessels, and other exhibits chronicling the history of Chesapeake Bay.
Meanwhile, wandering the town’s Historic District exposes you to well-preserved buildings and structures offering a snapshot of St. Michael’s heritage. Another unique way to explore the town would be to get on the water with Patriots Cruises for a relaxed cruise with narrations about top points of interest in the area. Also, local cuisine is served at The Crab Claw for some fresh seafood.
Thurmont
Thurmont is a small northern Maryland community located proximally to the Pennsylvania border. The town’s motto, “The Gateway to the Mountains,” clues you in on the natural splendor of the rolling hills and sprawling parks that define the majestic Catoctin Mountains, where the town is located. You can experience this natural scenery at Cunningham Falls State Park, home to the state’s highest cascading waterfall. Hikers are encouraged to wear comfortable walking shoes to explore the short hiking trail leading to the falls and carry a camera to capture some of the region’s wildlife.
Adjacent to Cunningham Falls State Park is Catoctin Mountain Park, another excellent spot for nature lovers with numerous recreation opportunities. From hiking, fishing, camping, and picnicking, it is the perfect playground for outdoor enthusiasts. One of the best times to be in Thurmont is in the fall when the town hosts Catoctin Colorfest. This popular arts festival draws more than 100,000 enthusiasts to celebrate local talent.
Chestertown
The past blends seamlessly with the present in this friendly Kent County Community, where you can experience well-preserved, ancient architecture and sample a bustling arts scene. History enthusiasts will discover the Historical Society of Kent County, which preserves the region’s historical heritage through artifacts, documents, publications, and other exhibits. Meanwhile, Chestertown’s artistic personality shines through numerous art venues, including the Garfield Center for the Arts, which hosts fascinating live shows.
A visit to the town wouldn’t be complete without tasting the famous Chesapeake Bay cuisine, prepared using locally sourced produce accessible at Chestertown Farmers Market. Besides shopping for fresh groceries, this is an excellent way to interact with the locals. When it’s time to explore the open spaces, the beautiful Wilmer Park checks every box. The natural space along Chester River offers plenty of outdoor activities and is ideal for relaxing and unwinding.
Oxford
Not to be confused with the English city or the other 30+ places in America bearing the same name, Oxford, Maryland, is a former colonial port with a rich history. Its walkable downtown features cozy streets lined with quaint stores for enjoying scanning. The Treasure Chest is open to select a souvenir from a gorgeous collection of antiques and handcrafted gifts, or there’s the Oxford Museum to look into the town’s history. Elsewhere, the Water’s Edge Museum displays paintings, literature, drawings, and other art forms by different artists, offering a rich cultural experience.
The town also boasts charming natural spaces, one of which can be experienced at Oxford Beach. Its laid-back atmosphere is excellent for sunbathing while enjoying stunning coastal views or savoring a wholesome outdoor lunch. Better yet, you might fancy a pleasant ride on the Oxford Bellevue Ferry to discover the town from the water.
Easton
Easton easily ranks among the best towns to visit in Maryland, a credit to its eclectic mix of fun attractions, promising to interest all types of travelers. Upon setting foot in the city, the first stop can be at the Academy Art Museum. This premium arts center showcases a charming collection of thought-provoking pieces and offers lessons on various creative techniques. If traveling with family, the kids will love exploring Idlewild Park for its playground and sports fields. Besides being a cozy space, it houses several play areas, including two horseshoe pits, swings, slides, and forts.
To look into the region’s rich history, the Talbot Historical Society offers different categories of exhibits housed inside the museum with the option to spend some quality time strolling its calm gardens. Lastly, the Amish Country Farmers Market is where shoppers find freshly baked delights like pies, donuts, and pretzels, or partake in casual dining.
St Mary’s City
Hosting a modest population of just about 1,000 residents, St. Mary’s City is one of the best towns to explore America’s colonial history. This former colonial town was the first European settlement in the state and hosts a treasure trove of historical sites, including ancient buildings, structures, and artifacts. Among the places to witness this living history is Historic St. Mary’s City, a renowned archeological museum with reproduced buildings that offer a snapshot of the bygone eras.
Other historical attractions, like St. John's Site Museum at Historic St. Mary's City, educate onlookers about the man who made the building in the 1600s, John Lewger. This stop is a free opportunity to discover how the archaeologists uncovered its artifacts, truly giving a unique experience for tourists. For a cozy overnight, The Inn at Broome Howard caters as a bed and breakfast with a fireplace, games, and a historical library.
Berlin
Although it shares a name with the famous German capital, Berlin, Maryland was inspired by an old local tavern called Burleigh Inn. The town, which forms part of the Maryland-Delaware Metropolitan Statistical Area, is laden with historical sites, with over 40 structures on the National Register of Historic Places. Strolling through the charming town center feels like stepping into a time capsule, with renovated and well-preserved structures from the Victorian, Federal, and 20th-century eras, taking visitors back in time. The rich past can be discovered at Calvin B. Taylor House, a historic mansion with diverse memorabilia from the old times.
Meanwhile, Assateague State Park offers a nice escape for outdoor lovers. This idyllic natural space on Assateague Island boasts a diverse ecosystem featuring sandy beaches, coastal bays, salt marshes, and maritime forests. After spending the day exploring the town, you can relax with a refreshing pint at Burley Oak Brewing Company while sampling the local nightlife.
Boonsboro
This quiet Maryland town is an excellent destination for tourists interested in American history. It was named after its founder, George Boone, and houses several historic sites that allow you to travel back in time. The Washington County Agricultural Education Center and Rural Heritage Museum are one such place. Here, you can check out several exhibits vividly portraying 20th-century life in Washington County. Meanwhile, the Boonsborough Museum of History preserves the memories of America’s bloody Civil War by displaying a collection of weaponry and other relics from the old conflict.
There is more to Boonsboro than its history that’s found when its open spaces are explored at Greenbrier State Park. This sprawling artificial lake is a prime spot for diverse outdoor adventures, drawing visitors interested in swimming, canoeing, fishing, and boating. Another exciting site you’ll want to check out is the Crystal Grottoes Caverns for a 30-minute walk of geological formations.
Kensington
Kensington is only a 33-minute drive from Washington, D.C., making it a worthy getaway from the country’s capital for a small-town feel. One of the most visited sites in the town is the Washington D.C. Temple, an architectural marvel and historical landmark that was the maiden Latter-day Saint church on the East Coast. Another great spot is Kensington’s Arts Theatre, which showcases exciting live shows popular among locals and visitors alike.
However, if desiring a little more outdoor time, activities to partake in are at St. Paul Park. Thanks to amenities such as a basketball court, picnic benches, a pavilion, and a youth ball field, it is a popular meeting point for the town’s residents.
New Market
New Market is a Frederick County town oozing timeless charm. Billing itself as the “Antiques Capital of Maryland,” the town is known for its numerous antique shops, including Robert Esterly Antiques, which has a vast collection of high-quality antiques from different eras. This would be an excellent place to hunt for souvenirs to kick off the itinerary in New Market. Alternatively, a stroll down historic Main Street allows for the town’s unique aura to soak in and the quaint businesses lining the lively avenue can be explored.
Keeping up with the historic theme, the Vintage Restaurant promises an old-time feel with delicious meals. The kids will love the waffle bar served at the annual Sunday brunch, starting at $29.99 per person, $11.99 for kids 12 and below, and kids under 3 are free. Finally, tourists working up a thirst can grab a drink at the Derby Restaurant & Bar after an eventful day exploring the town for a more laid-back dining experience.
Princess Anne
As its name would suggest, Princess Anne is a fairytale destination beaming with a charming historical vibe. It was named after King George II’s daughter and houses gorgeous, impressively preserved Victorian homes. The town’s charming natural scenery can be explored at Manokin River Park, where scenic views of Manokin River and isolated picnic areas culminate in the perfect outdoor chill spot.
Another pleasant spot to visit is Somerset Choice Station Antiques, home to cute vintage items that will make excellent souvenirs to take back home after the visit. For a slice of history, scheduled tours of Teackle Mansion highlight a gorgeous ancient homestead constructed in the early 1800s.
Wrapping Up
These beautiful locations truly embody the essence of Maryland’s small-town charm. They offer a unique mix of attractions rarely found in the big cities, promising a unique experience that will have visitors undoubtedly planning a return trip. Whether embarking on a solo excursion or taking a romantic couple’s vacation, these unforgettable towns in Maryland are worth prioritizing on the itinerary.
