Part of St. Michaels Harbor in historic Saint Michaels, Maryland, in spring

10 Best Small Towns To Visit In Maryland

Maryland is a fascinating state tucked away on the American Eastern Coast. There are many small towns to visit in Maryland providing various attractions bound to please any traveler, from historical sites, beautiful scenery, lively cultural scenes, and mouthwatering seafood. Maryland also has an abundance, providing a nice respite from the busy metropolitan life. 

Maryland's small towns are a lasting memorial to the state's intriguing past and stunning landscape, from colonial-era communities to seaside havens and alpine getaways. Let's look at the top ten small towns in Maryland, each featuring a distinct identity and tourist sites that will take visitors back in time and make them feel at home.

St Mary's City

Historic St Mary’s City
Historic St Mary’s City

St. Mary's City, the original capital of Maryland, is a fascinating location rich in history. The place is home to an impressive collection of historically accurate reproductions of colonial structures, giving tourists a view into Maryland's early days. Visitors can tour the State House, an exact model of the historic building from the seventeenth century, and embark on the Maryland Dove, a recreation of the ship that visited the New World. Travelers should visit the St. Mary's City Museum to go further into the past. There, displays and artifacts recount the tale of the town's first inhabitants. The tranquil St. John's Pond and gorgeous St. Mary's River enhance the town's appeal. It is an excellent place to look into a quaint historic Maryland town. 

Havre de Grace

Distant Lighthouse in Havre De Grace, Maryland
Distant Lighthouse in Havre De Grace, Maryland

Maryland's Havre de Grace is a little town full of coastal beauty located along the magnificent Chesapeake Bay. The Concord Point Lighthouse, directing sailors since 1827, serves as one of its most recognizable sights. Visitors can discover the lovely city center with its chic stores and art galleries or enjoy a relaxing walk along the Promenade, offering expansive views of the bay. Tourists interested in history can check out the Havre de Grace Decoy Museum, which highlights the community's long practice of carving decoys. Travelers can also discover the Delaware and Chesapeake Canal's heritage at the Susquehanna Museum in the Lock House.

Thurmont

Corner of Main and Water in downtown Thurmont, By Andrew Bain - Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=7763579
Corner of Main and Water in downtown Thurmont, By Andrew Bain - Own work, CC BY-SA 3.0, File:Thurmont MD Corner of Main and Water.jpg - Wikimedia Commons

Thurmont, tucked away in the picturesque Catoctin Mountains, is a paradise for history enthusiasts and nature lovers. Visitors can admire the largest gushing waterfall in Maryland in Cunningham Falls State Park, which also has charming routes. There are also options for hiking, camping, and wildlife viewing in the nearby Catoctin Mountain Park. At the National Shrine of St. Elizabeth Ann Seton, tourists can explore the old structures and discover more about the first native-born saint of America. Thurmont is particularly well-known for its yearly Colorfest arts and crafts festival, which draws people from near and far every autumn. Visitors are sure to have a captivating vacation in Thurmont.

New Market

Wooden iron bench on isolated colonial street in New Market
Wooden iron bench on isolated colonial street in New Market

Visitors can step back in time in the lovely town of New Market. Tourists can browse the one-of-a-kind stores and boutiques while strolling along Main Street, full of beautifully restored nineteenth-century structures. The New Market Historic District, where one can see beautiful homes like the renowned Hargett House, should not be missed. The New Market Museum, located in a former school, is open to history enthusiasts and features artifacts and displays relating to the town's past. The Original Playhouse, a children's space, is an excellent option for kids. Outdoor enthusiasts can enjoy the picturesque surroundings of the Frederick Municipal Forest in the vicinity or take a scenic walk along the nearby Appalachian Trail.

Chesapeake City

View of Chesapeake City from the Chesapeake City Bridge, Maryland
View of Chesapeake City from the Chesapeake City Bridge, Maryland

With its scenic coastline and charming history, Chesapeake City promises a peaceful refuge. Tourists can know about the Delaware and Chesapeake Canal's impact on the area's history as they stroll around the C&D Canal Museum. The Ben Cardin track provides excellent hiking options in a peaceful setting. Visitors can also browse unusual stores and art galleries while admiring the town's Victorian-era structures, adding to its attractiveness. Outdoor enthusiasts can take a bike ride along the picturesque canal trail or go boating or fishing in the Chesapeake Bay.

St. Michaels

Some of the shops and stores in St Michaels, MD along the town's main street, via George Sheldon / Shutterstock.com
Some of the shops and stores in St Michaels, MD along the town's main street, via George Sheldon / Shutterstock.com

St. Michaels is a charming coastal community noted for its maritime past and small-town atmosphere. Visitors can discover the area's naval legacy at the Chesapeake Bay Maritime Museum and even set out on a vintage skipjack. People can stroll through the quaint alleyways dotted with specialty stores, art museums, and eateries. Tourists can take a picturesque tour on the Miles River or explore the Hooper Strait Lighthouse, serving as the community's unmistakable symbol. Travelers can also enjoy a delectable crab meal at any neighborhood seafood establishment for a distinctive experience. St. Michaels is a must-see location due to its charming harbor, magnificent sunsets, and welcoming community.

Oxford

A beautiful view of Oxford, Maryland
A beautiful view of Oxford, Maryland

Located on the shores of the Tred Avon River, Oxford is an idyllic town oozing traditional beauty and providing a window into the state's historical past. Visitors can observe the exquisite ancient residences, some dating to the eighteenth century, as they casually wander along the waterfront. People can also tour the exhibitions at the Oxford Museum to discover more about Oxford's nautical past and historical artifacts. Travelers should not skip the renowned Oxford-Bellevue Ferry, among the country's oldest still-running privately run ferries. Visitors can take in the tranquil surroundings while dining at the waterfront establishments and savoring fresh seafood. It is one of the best small towns to visit in Maryland that takes visitors back in time with its calm ambiance and beautifully conserved architecture.

Easton

Autumn color and houses along Goldsborough Street, in Easton, Maryland
Autumn color and houses along Goldsborough Street, in Easton, Maryland

Easton is a beautiful town bursting with cultural riches, located in the center of Maryland's Eastern Bank. Visitors can discover the lovely downtown district with its boutique stores, galleries, and lanes surrounded by trees. People can indulge in the town's past at the Historical Society of Talbot County, featuring displays and artifacts highlighting the area's past. Tourists should not skip the Academy Art Museum, set in a gorgeously renovated nineteenth-century structure featuring a sizable collection of works by regional and worldwide artists. Chesapeake Views cycle loop is a fantastic place for those who enjoy the outdoors. Easton is a fascinating location with an abundance of cultural heritage and natural splendor appealing to everyone.

Berlin

Autumn color and houses along Goldsborough Street, in Easton, Maryland
Street view in Berlin, Maryland

Tourists will feel in a different era as they enter the quaint village of Maryland's Berlin. The place oozes a small-town vibe and a rich past with its well-conserved historic downtown, full of structures from the Victorian era. The Atlantic Hotel, a Victorian-style jewel continue to welcome guests since 1895, is one of the town's landmark structures that showcases its distinctive architectural heritage. The Calvin B. Taylor House Museum attracts visitors interested in history and provides a look into the town's legacy through its displays and artifacts. The Burley Oak Brewing Company is open for visitors to explore and partake in various beverages. Berlin is a charming city that enchants travelers with its traditional attractiveness thanks to its charming streets, warm atmosphere, and active arts scene.

Crisfield

The J. Millard Tawes Historical Museum, a maritime museum in Crisfield, a town on the Chesapeake Bay
The J. Millard Tawes Historical Museum, a maritime museum in Crisfield, a town on the Chesapeake Bay

Crisfield is a coastal community with a strong nautical past, located on the picturesque Eastern Shore. Crisfield, also referred to as the "Crab Capital of the World," is well-known for its delicious and thriving seafood sector. Visitors can discover the town's lovely stores, seafood markets, and riverfront eateries in the traditional downtown. The Somers Cove Marina is a thriving gathering place for boating lovers with options for fishing, crabbing, and sailing. Additionally, Crisfield serves as a gateway to the stunning Tangier and Smith Islands, where travelers can explore their distinct cultures and breathtaking natural settings. Crisfield provides visitors with a lovely retreat into Maryland's marine past with its scenic waterfront, warm community, and classic coastal elegance.

Every traveler can expect a fascinating and enlightening time in Maryland, regardless of their interests—whether they are looking for a historical tour, an outdoor adventure, a gastronomic excursion, or a cultural immersion. Visitors will discover a raw and classic side when visiting the small towns in Maryland. 

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