9 Towns In Maryland That Were Frozen In Time
Maryland is a state rich in history, where small towns seem to transport visitors to another era. From picturesque Chesapeake Bay waterfronts to colonial-era architecture, the nine towns on this list have preserved their unique heritage, making them ideal destinations for anyone seeking to experience the beauty of the past. Whether you are an avid history buff, a lover of scenic landscapes, or simply searching for a peaceful getaway, these frozen-in-time towns offer something for every traveler.
Easton
Downtown Easton in Maryland.
Easton, a beautiful town on Maryland’s Eastern Shore, exudes a small-town charm with its tree-lined streets with the heart of the town is its vibrant downtown area, home to well-preserved 18th and 19th-century buildings and cultural institutions like the Academy Art Museum and Talbot Historical Society. The annual Plein Air Festival, held in July, celebrates the community and its strong artistic heritage. Visitors to Easton can also enjoy outdoor activities, including hiking and biking along the Easton Rails-to-Trails network, or take a boat ride along the Choptank River to explore the local landscape.
Berlin
Street view with shops in Berlin, Maryland. Editorial credit: Kosoff / Shutterstock.com
Berlin is an exceptionally well-preserved town known for its Victorian architecture and its role in Maryland’s history. Strolling through its streets feels like stepping back in time, with beautiful storefronts, quaint cafes, and antique stores like Uptown Emporium, Outten’s Delites, and Treasure Cove Shoppe. Downtown Berlin is also home to the Mermaid Museum, which explores mermaid myths and artifacts. Fun Main Street events like the Peach Festival and Oktoberfest celebrate the community with music, food, and local crafts. Additionally, outdoor enthusiasts will enjoy visiting nearby Assateague Island, known for its wild ponies and pristine beaches, where hiking, biking, and birdwatching are popular activities.
Annapolis
Downtown view of Main Street with the State House in Annapolis, Maryland.
As Maryland's capital and a town steeped in colonial history, Annapolis offers an enchanting combination of charming streets and significant landmarks. The historic district is home to stunning 18th-century buildings, including the Maryland State House, which is the oldest state capitol in continuous legislative use in the United States. History buffs will enjoy visiting the William Paca House and Garden, once home to a signer of the Declaration of Independence, or exploring the United States Naval Academy with its beautiful architecture and fascinating history. After soaking in the town’s deep history, head to the Annapolis waterfront for a range of activities, from sailing on the Chesapeake Bay to enjoying strolls along the dock area.
Saint Mary's City
Seminary at Mount Saint Mary's University in Emmitsburg, Maryland.
Saint Mary's City, on the shores of the Chesapeake Bay, is one of Maryland's oldest and most significant colonial settlements. As the site of the first permanent English colony in Maryland, it is a must-visit for anyone interested in early American history. Saint Mary's City, a fascinating living history museum, offers an in-depth look at the town's founding and its role in religious freedom and the state's development. Visitors to the site can explore reconstructed 17th-century buildings, including a State House and a chapel, and tour archaeological sites that reveal the town's original layout. The natural beauty of the surrounding marshes and waterways also offers opportunities for kayaking and birdwatching.
Salisbury
Aerial view of Salisbury City Park bridge and lake in Salisbury, Maryland.
Situated on the Eastern Shore along the way to Maryland’s main beach destination, Ocean City, Salisbury blends a rich history with a lively atmosphere. The town’s historic district features a variety of architectural gems, from grand Victorian houses to brick buildings dating back to the 19th century. Salisbury is home to the Salisbury Zoo, a free-to-visit facility that showcases native wildlife. The nearby Pemberton Historical Park, set on 262 acres of land, offers hiking trails and picnic spots for those looking to enjoy the outdoors. Salisbury also hosts the annual Maryland Folk Festival, which celebrates the local culture through music, arts, and food.
Cambridge
Buildings along Poplar Street in downtown Cambridge, Maryland. Editorial credit: NLM Photo / Shutterstock.com
Cambridge, along the Choptank River, boasts a vibrant history dating back to the 1600s. The town’s well-preserved Victorian architecture is evident throughout the historic district, especially in its many beautiful waterfront homes. The Dorchester County Historical Society Museum provides a deep dive into the region's past, while visitors can also explore the Harriet Tubman Underground Railroad Visitor Center, dedicated to the life and legacy of the famed abolitionist. Outdoor lovers will enjoy the Blackwater National Wildlife Refuge, where opportunities for birdwatching, hiking, and wildlife photography abound.
Chestertown
Aerial view of colonial Chestertown on Chesapeake Bay in Maryland.
Known for its well-preserved colonial architecture, Chestertown is a quaint town along the Chester River. Walking through its downtown area, visitors will find charming shops, art galleries, and local restaurants like Watershed Alley and Modern Stone Age Kitchen. Chestertown's maritime history is on display at the Chestertown Marina and the nearby Kent County Historical Society Museum, where exhibits highlight the town’s role in the 18th-century tobacco trade. The town celebrates the Chestertown Tea Party Festival each spring, commemorating a 1774 act of civic defiance. The surrounding natural beauty also makes Chestertown a great destination for kayaking and boat tours.
Stevensville
Downtown Stevensville, Maryland.
On Kent Island, the one-time railroad and ferry hub of Stevensville offers a peaceful retreat with a blend of natural beauty and charm. The town is home to the classic Stevensville Train Station and close to the Chesapeake Bay Environmental Center, which provides educational programs about the area’s ecology and wildlife. For those interested in outdoor activities, the nearby Matapeake Beach offers spectacular views of Chesapeake Bay, while the island’s trails provide opportunities for hiking and biking. Stevensville also hosts a number of local festivals, including the annual Kent Island Day, which celebrates the area's heritage and culture.
Oxford
The Sultana, a reproduction of a Boston-built merchant vessel, in Oxford, Maryland. Editorial credit: JE Dean / Shutterstock.com
Oxford, one of Maryland’s oldest towns, is a hidden gem on the Eastern Shore. Its streets are lined with colonial-era homes and the Customs House, and the Oxford Museum provides insight into the town’s past four centuries. Oxford is known for its role in the Chesapeake Bay’s shipping industry, and visitors can take a ride on the Oxford-Bellevue Ferry, which has been operating in various iterations for almost 350 years, for stunning views from the water. Nature lovers will appreciate the walking trails around the town, as well as the chance to explore nearby waterways by kayak or canoe.
Step Back in Time in Maryland's Most Historic Towns
From the colonial landmarks of Annapolis to the peaceful streets of Oxford, these nine towns in Maryland have successfully preserved their rich histories and natural beauty. Each town offers a unique window into the past, with colonial architecture, museums, and local festivals that make them stand out as frozen-in-time gems. Whether you are exploring the waterways, hiking through lush nature reserves, or learning about the state's pivotal moments in American history, these towns provide the perfect escape for those looking to enjoy the past while embracing the present.
