10 Oldest Founded Small Towns to Visit in Maryland in 2024

Maryland is one of the most toured states on the East Coast. Between the picturesque Chesapeake Bay and the majestic Blue Ridge Mountains, it houses charming communities that have stood the test of time, dating back to the pre-Revolutionary War era. From birthing iconic presidents to playing a vital role in landmark national events, these communities boast rich historical heritages that cumulatively tell the captivating story of the Old Line State.

The oldest small towns to visit in Maryland promise an immersive experience, exposing first-timers to captivating local folklore, rare state history, and landmark national sites. Their well-preserved historic districts enable stepping back in time by visiting historic mansions and lodging in medieval inns. These wonderful Maryland destinations set the stage for a riveting trip down memory lane.

Berlin

This Victorian town in Worcester County delights tourists with its historic mansions, quaint museums, and trademark Southern hospitality. Berlin was incorporated in 1868, but the town’s legacy dates back to earlier periods. This is evidenced by well-preserved landmarks like the Calvin B. Taylor House, an 1832 Federal-style mansion with antique artifacts and memorabilia for the period. The Mermaid Museum reveals a quirky collection of exhibits centered around the mermaids. These range from toys and books to souvenirs and apparel, which always intrigue newcomers.

Attending the Berlin Farmers Market is a chance to interact with a welcoming local community that makes you feel at home. The gathering brings together growers and crafters from the region, and the atmosphere is always festive as buyers comb through fresh produce and handicrafts.

Cambridge

Nostalgic memories await in this picturesque Chesapeake Bay community, which traces its incorporation back to 1793. Cambridge hosts several historical landmarks, led by the Harriet Tubman Museum & Educational Center, which preserves vital aspects of the state's past. This fascinating venue provides a window to several landmark periods, notably the Underground Railroad and the Civil War. The Choptank River Lighthouse represents Cambridge's long-standing maritime heritage and rises above the calm waters of the Chesapeake Bay.

Not too far off, Long Wharf Park provides access to the sandy shoreline trails with exquisite water vistas. It is a popular outdoor space where visitors and locals come to picnic, fish, and just chill out.

Cumberland

This lovely college town in the Appalachian Mountains embodies the beauty of Maryland's backcountry. Guests here love to board the Western Maryland Scenic Railroad for front-seat views of the Allegheny Mountains during an easygoing sightseeing tour. Cumberland was founded in 1787 and has a charming history that vacationers can learn more about inside the Allegany Museum. Its vast collection features over 50,000 artifacts, ranging from old photographs, historical artifacts, art, relics, and other memorabilia that vividly detail the region's past periods.

Walking around the historic district, you will encounter gems like the Gordon-Roberts House, a gorgeous 1800s mansion with Victorian furnishings and artifacts. Cumberland showcases its artistic personality by staging entertaining live performances at the Cumberland Theatre.

Havre De Grace

Strategically situated on the confluence of the Chesapeake Bay and the Susquehanna River, this delightful community stands out for its cluster of museums, which preserve different aspects of its diverse history. Historians are spoilt for choice and can discover the town's rich nautical heritage at the Havre de Grace Maritime Museum. Inside the facility, various exhibits chronicle the town's fishing and crabbing exploits over the years. Meanwhile, the Lock House Museum focuses on the working of the river canals in a well-preserved 1840s home.

You cannot miss the imposing Friends-Concord Point Lighthouse in Havre de Grace. The 36-foot lighthouse was erected in 1827 and reminds visitors of the town's vital role in marine navigation along the Chesapeake Bay.

Leonardtown

Leonardtown was founded in 1660 with a different name, making it one of the oldest towns to visit in Maryland. Fortunately, a diverse mix of experiences in this adorable community guarantees to make your tour worthwhile. The Old Jail Museum & Leonardtown Visitor Center is an excellent first stop. Constructed in 1876, it previews the town's history from a prisoner's perspective and provides information on the significant points of interest. The historical experience resumes at Tudor Hall, an 18th-century Georgian mansion with a distinct red-brick construction.

Those who lean towards cultural pursuits can find intimate pieces inside the North End Gallery. St. Mary's County's oldest gallery exhibits a diverse collection featuring over 30 regional artists. The cultural experience is even more immersive at Shepherd's Old Field Market, which provides a charged social atmosphere with restaurants, stores, antique shops, and more.

Oxford

Oxford's founding stretches back to 1683. The town houses several sites where guests can explore its history, starting with the Oxford Museum. Stored inside is a diverse artifact collection chronicling more than three centuries of local history. It also hosts the Water's Edge Museum, which focuses on local heritage from the perspective of founding black families. Browsing interactive exhibits introduce guests to black sailors, farmers, military men, and musicians who have had an impact on local culture.

Visitors can take advantage of Oxford's waterfront location to venture into the open sea by riding the Oxford Bellevue Ferry. However, if you are too coy to get on the water, you can remain on dry land and enjoy entertaining live theater at Tred Avon Players.

Thurmont

Considered a gateway to the mountains, Thurmont is endowed with stunning natural scenery, flanked by gorgeous views of the Catoctin Mountain Peaks. This means countless outdoor adventures are available to visitors, from hiking and picnicking to nature viewing across the beautiful Cunningham Falls State Park. Another great leeway to the great outdoors lies in Catoctin Mountain Park, which houses 25 miles of alpine trails and multiple vantage points to soak up the lush surroundings.

Beyond the unmatched outdoors, Thurmont has a rich history, given its 1751 founding. Newcomers curious about its past can visit the Thurmont Historical Society, which preserves the town's historic and cultural history. Meanwhile, art lovers will have an enjoyable time perusing the world-class art at the Rebecca Pearl Gallery.

St. Michaels

Steeped in maritime history and riddled with iconic landmarks, this lovely coastal community in Talbot County is a prime destination for the historically inclined. St. Michaels was founded in the mid-1600s by English settlers. Its unprecedented legacy can be explored inside the St. Michaels Museum. Although relatively small, this vital venue documents the town's history from Colonial times to the present inside a rustic 19th-century structure.

The Chesapeake Bay Maritime Museum lets visitors learn more about St. Michael's nautical history by exhibiting a diverse selection of related artifacts. Several antique lighthouses across the town bear proof of its longstanding maritime heritage. You cannot miss the iconic Hooper Strait Lighthouse, which was initially erected in 1879.

Chestertown

This artsy community in Kent County excites visitors with its impressive combination of unique historical heritage and thriving art culture. Chestertown's founding goes back to the early 1700s, evidenced by the cluster of old buildings dotting its historic downtown region. The town invites historians to discover its beautiful heritage at the Historical Society of Kent County, which not only focuses on Chestertown's past but also that of the surrounding region.

Some antique downtown structures house quaint art centers that draw visitors from all over the state. The Garfield Center for the Arts is a recognized venue that constantly stages enthralling shows, including drama, concerts, and musicals, to support the creative community. However, those who lean towards visual arts can stop by the MassoniArt Gallery to admire stunning artworks.

Annapolis

Maryland's capital city is an impressive destination that draws millions of annual visitors with its array of experiences. Historically, it is home to the country's oldest state house in continuous legislative function. The Maryland State House is a top local attraction sporting a Georgian architectural style from the 18th century. However, there is no shortage of historical sites in Annapolis, including the William Paca House & Garden from the mid-1700s and the Hammond-Harwood Museum, home to an exciting collection of paintings, artifacts, and furnishings from the 18th century.

The town also houses the Annapolis Maritime Museum & Park, where guests can learn about the local nautical heritage. When you finish the historical experience, you can relax and take it easy at the scenic Quiet Waters Park.

The towns featured provide a glimpse into Maryland's long and storied past, from colonial settlements to Gilded Age retreats. Wandering through well-preserved downtowns surrounded by historical markers and architectural gems transports visitors through the centuries. Those interested in American history will find each location an educational and visual showcase of the state's contributions. Any of these historical towns to visit in Maryland is a route to explore multiple colonial and Victorian coastal villages, guaranteeing new cultural insights and appreciation for the state's role in shaping early America.