These Small Towns in Delaware Have the Best Historic Districts

Delaware is the oldest state in the USA and was the first to ratify the new country’s constitution on December 7, 1787. Yet despite being the country's second smallest state in terms of size (it covers an area of just under 2,000 square miles) and the smallest in terms of population (a little over a million), Delaware boasts a surprising number of interesting small towns that have managed to preserve their past.

These small towns in the “First State” are also home to some of the most interesting historic districts in the mid-Atlantic region. Serving as living museums, their cobblestone streets and perfectly preserved old colonial homes have witnessed events that have not only shaped Delaware but have also impacted the United States as a whole. These small towns in Delaware have some of the best historic districts.

Lewes

Lewes was settled by the Dutch in 1631 on Delaware Bay, which has led to its being known as  the "First Town in the First State." While none of the original settlements remains, later buildings from the 18th and 19th centuries can be seen as a well-preserved historic district. Included among its 122 facilities are the aptly named Cannonball House, now a maritime museum that still bears scars from a bombardment during the War of 1812, and Ryves Holt House, built in 1665, and the state’s oldest surviving home.

Another important landmark is the Zwaanendael Museum. This fascinating attraction features displays relating to Delaware's first European colony, Swanendael, established by the Dutch in 1631 and was inspired by Hoorn City Hall in the Netherlands.

New Castle

Travel an hour north of Lewes toward Wilmington, and visitors will find New Castle, another early Dutch settlement from the 1600s worth visiting. Set on the Delaware River, New Castle's charming historic district is one of the prettiest on the East Coast. It features picturesque cobblestone streets lined with well-preserved buildings dating from the 17th, 18th, and 19th centuries.

Arguably the most important historic attraction in New Castle, the attractive New Castle Court House Museum dates back to 1732 and once served as Delaware's first court and state capitol, playing a pivotal role in the state's move towards independence from Pennsylvania and England. Today, it stands as a museum detailing Delaware's journey to statehood. References to the community's Dutch roots can be found in Dutch House, one of the town’s oldest dwellings with displays relating to these first European settlers.

Milford

Sitting on the banks of the Mispillion River, Milford’s riverside setting long ago cemented the town’s strategic importance. Founded in the late 18th century, Milford's rich heritage is displayed in its historic downtown district. Here, you’ll find points of interest such as Parson Thorne Mansion, a historic home and now museum built in the 1730s boasting elegant Georgian architecture and charming gardens.

The Milford Shipyard Area is another significant historic site to include on your Delaware travel itinerary. Though no longer operational, the town’s maritime legacy lives on through preserved buildings and historical markers.

Odessa

Founded in the 1700s on the site of an earlier Dutch settlement and named after the vital port city in Ukraine, Odessa’s historic downtown, with its collection of 82 old buildings, is fun to explore. Although home to just under 400 souls, this small town boasts deep ties to the Underground Railroad and the country’s colonial era. Highlights include Corbit-Sharp House, constructed in the 1770s in Georgian style and now housing an extensive collection of authentic 18th-century furnishings and interiors.

Adjacent to Corbit-Sharp House is the Wilson-Warner House, another striking example of Georgian architecture. Built in 1769, it’s now a museum and event space.

Dover

Despite being Delaware’s capital, Dover’s relatively tiny population of just 38,000 residents, along with its two picturesque historic districts, give it a distinctly small-town vibe. Established in 1683, the oldest of the town's homes can be found in the Victorian Dover Historic District, which features 482 ancient buildings, including many from the early 1800s to the early 1900s. Among them are Wesley United Methodist Church, built in 1850; Whatcoat United Methodist Church (1871); and the town’s train station from around 1860.

The Dover Green Historic District is another must-visit. This charming area is centered around the village-like Green, an essential landmark for its role as the site where Delaware ratified the U.S. Constitution. Next to the Green stands the Old State House, a Georgian-style structure with grand staircases, ornate woodwork, and a bell tower that served as the state's first permanent capitol building.

Delaware City

Despite its rather lofty name, Delaware City’s population of under 2,000 people suggests this charming destination is, at heart, every inch a small town. Located at the convergence of the Delaware River and the Chesapeake and Delaware Canal (opened in 1829), this charming community has served as a crossroads to the region’s commerce, military, and maritime activities since it was founded in 1801. Delaware City’s historic district features a well-preserved collection of Victorian and Federal-style homes and buildings from this period.

Your visit should include Fort Delaware State Park on Pea Patch Island. Accessible only by ferry from the town’s waterfront, this former Civil War-era Union fortress features a unique five-sided design and also serves as a prison for Confederate prisoners of war. It’s now a fascinating living museum featuring costumed interpreters that offers a glimpse into life during the turbulent 1860s.

Smyrna

Located just 20 minutes drive north of Dover, Smyrna was established in the early 18th century and has done a stellar job of preserving and showcasing its past. Start by exploring the best things to do in Smyrna with a visit to the Smyrna Historic District, which comprises several blocks near the town’s Main Street.

Historic highlights of this collection of over 850 buildings and structures include the Smyrna Opera House. Constructed in the 1860s, it once served as the town hall and is now a cultural center. Other highlights include the Irishtown Tavern, built in 17710, and Asbury Methodist Church, dating from 1845.

The Final Word

Whether travelers are looking to explore its fascinating maritime history or its role in the War of 1812, or maybe just looking for examples of well-preserved historic architecture from the 1700s to the early 1900s, these East Coast small towns with the best historic districts are well worth including on any list of places to visit in Delaware. With a mixture of old-world charm and lovely landscapes as well, Delaware does not disappoint.