Aerial sunset panorama of Havre de Grace, Maryland, with vibrant orange sky and clouds reflecting on the Susquehanna River and the Chesapeake Bay.

These Small Towns in the Mid-Atlantic Have the Best Historic Districts

The Mid-Atlantic is a region of the upper eastern coast of the United States that is home to an abundance of cultural landmarks worth traveling to. States in this area consist of Delaware, Maryland, New Jersey, New York, Pennsylvania, and more, making it one of the most highly populated regions of the country. Many of the original European colonies are located here, and because of this, there is a high level of historically recognized districts in its many towns and cities, small and large. Discover seven smaller towns that are worth visiting if learning about history sounds like an ideal way to spend a road trip.

Chestertown, Maryland

Chestertown, Maryland, United States, seat of Kent County in the Chesapeake Bay region.
Chestertown, Maryland, United States, in the Chesapeake Bay region. Editorial credit: EQRoy /

Chestertown boasts a rich colonial history evident in its well-preserved historic district, featuring notable landmarks like the Geddes-Piper House and the renowned Washington College. Established in 1706, the town played a significant role in trade and shipping during the colonial era. Beyond its history, Chestertown charms visitors with its vibrant arts scene, highlighted by the annual Chestertown Jazz Festival and thriving local galleries. Be sure to visit the John L Stam House if you are looking for a place to stay overnight with a historical twist. This antique inn is an excellent example of a well-preserved archwire from time past, being initially built in the 1850s. 

Looking to stretch your legs and enjoy some of the natural scenery of this area? Take a stroll along the Chestertown Historic Waterfront to the scenic Wilmer Park. 

Staunton, Virginia

Downtown Historic Staunton, birthplace of President Woodrow Wilson, in Staunton, Virginia.
Downtown Historic Staunton, Virginia. Editorial credit: MargJohnsonVA /

In the heart of Virginia, in the foothills of the Appalachian Mountains, sits the town of Staunton, with a population of nearly 26,000 residents. It is both a historic hot spot and a great kickoff point for outdoor adventurers looking to hike, camp, and/or fish in the nearby forested hills.  

Staunton's historic district showcases architectural gems like the Stonewall Jackson Hotel and the Victorian-style Warehouses. With roots dating back to the 18th century, Staunton thrived as a center for trade and industry. Notably, it's the birthplace of Woodrow Wilson, adding presidential significance to its history. Today, Staunton enchants with its Shakespearean theater and flourishing farm-to-table dining scene.

Definitely check out this town if you're looking for a historic district that is not necessarily near the coastline. 

Lewes, Deleware

Aerial view of Lewes, Delaware, U.S.A, showcasing the beach town, fishing port, and waterfront residential homes along the canal.
Aerial view of Lewes, Delaware, U.S.A. Editorial credit: Khairil Azhar Junos /

Deleware is one of the smallest states in the United States, both by population and size, with a little over a million residents and covering a mere 2,489 square miles. But, because of its strategic position along the Atlantic coast, it has been populated by European settlers for many centuries and native populations for millennia. 

Lewes is one of such towns that has a well-known historic district that features landmarks such as the Cannonball House and the Ryves Holt House, dating back to the Dutch settlement in the 17th century. As one of the earliest European colonies in Delaware, Lewes witnessed pivotal events like the Battle of Lewes in 1813 during the War of 1812. Besides its historical allure, Lewes captivates with its picturesque beaches and annual Cape May-Lewes Ferry festivities.

Shepherdstown, West Virginia

View of German Street in Shepherdstown, West Virginia, United States, featuring cars and people on a cloudy day.

German Street in Shepherdstown, West Virginia, United States. Editorial credit: Alizada Studios /

Seated on the legendary Potomac River, Shepherdstown, West Virginia, was a strategic point of contention during the Civil War. Even before the bloodiest conflict on American soil took place, this small town was important for trade and other industries that supported the area's population for centuries. 

Shepherdstown boasts well-preserved architectural treasures like the Shepherdstown Museum and the Entler Hotel. Founded in 1762, the town played a crucial role in the Civil War, hosting the Battle of Shepherdstown in 1862. Today, it preserves its past through charming cobblestone streets and annual events like the Contemporary American Theater Festival, attracting culture enthusiasts and history buffs alike.

Hiking and other outdoor activities are also incredibly popular in and around Shepherdstown, with parks like Chesapeake and Ohio Canal National Historical Park nearby. 

Haddonfield, New Jersey

Historic Haddonfield, New Jersey, USA - A significant paleontology site in Camden County, originally inhabited by Lenni Lenape Native Americans.
Historic Haddonfield, New Jersey, USA. Editorial credit: EQRoy /

This suburb of Philadelphia is sure to give you a taste of the dense city life that is common in the mid-Atlantic region. Still with a population of only around 12,500 residents, Haddonfield is technically considered a small town. Like many cities and towns in New Jersey, it holds its fair share of historic gems to see during your stay. 

Haddonfield's downtown historic district features landmarks like the Indian King Tavern and the Hadrosaurus Foulkii Statue, commemorating the discovery of the first nearly complete dinosaur skeleton in North America. Established in 1701, Haddonfield thrived as an agricultural hub before evolving into a vibrant suburban community. Beyond its historical significance, Haddonfield delights visitors with its quaint boutiques and picturesque parks.

Scenic walks can be had along the Cooper River if you are looking to break away from the city-based activities for a while. 

Lewistown, Pennsylvania

Monument Square in Lewistown, Pennsylvania, USA - A memorial honoring the Logan Guards, a militia group from the US Civil War era, located at Main and Market Streets.
Monument Square in Lewistown, Pennsylvania, USA. Editorial credit: George Sheldon /

Smack dab in the center of Pennsylvania is Lewiston, a quaint town of around 8,600 residents. Besides the many outdoor recreational activities that can be found nearby along the Juniata River, this town hosts a plethora of historical sights to see and learn about. 

Lewistown's historic district showcases architectural gems like the McCoy House and the Montgomery Ward Building. Founded in 1790, the town flourished as a center for manufacturing and transportation, spurred by its location along the Juniata River. 

While its history is evident in its well-preserved buildings, Lewistown also offers outdoor enthusiasts access to nearby hiking trails and fishing spots, as mentioned earlier. A short drive northeast of town is the Arch Rock Formation, both a historic point and a beautiful place to take photos. 

Havre de Grace, Maryland

Havre de Grace, Maryland during the summer season.

Havre de Grace, Maryland, during the summer season.

This idyllic town and the head of Chesapeake Bay on the Susquehanna River is both a historic strategic point and a great place to visit on a trip. It is also quite lovely to live in, being situated between the metro cities of Baltimore, Washington, and Philadelphia.

Havre de Grace's historic district contains must-see destinations like the Concord Point Lighthouse and the Decoy Museum, reflecting its maritime heritage dating back to the 17th century. Positioned at the mouth of the Susquehanna River, the town played a pivotal role in trade and shipping during the colonial era. Today, Havre de Grace enchants with its waterfront promenade and annual events like the War of 1812 reenactments, attracting history enthusiasts and nature lovers alike.

Be sure to catch a beautiful sunrise or sunset over the bay at Millard Tydings Memorial Park. 

Discover the Historical Tapestry of the Mid-Atlantic

As your journey through the Mid-Atlantic's small towns draws to a close, you may be left with a profound appreciation for their historical richness and charm. From the cobblestone streets of Chestertown to the maritime heritage of Havre de Grace, each town has offered a unique window into America's past. But beyond their historical significance, these towns have demonstrated resilience and vitality, fostering vibrant communities and cultural experiences. 

Definitely use this list as a starting point when planning your next road trip through the mid-Atlantic region. 

  1. Home
  2. Places
  3. Cities
  4. These Small Towns in the Mid-Atlantic Have the Best Historic Districts

More in Places