Chestertown Historic District | Ocean City

The Chestertown Historic District, located in Chestertown, Maryland, is one of the most prominent and well-preserved historic districts on Maryland’s Eastern Shore. It reflects the town’s important role as a colonial port and commercial center, as well as its architectural evolution from the 18th century through the 19th century. The district was officially designated a National Historic Landmark in 1970, with expansions in later years to protect a broader area that captures the historical and cultural fabric of the town.

Historical Background

Chestertown was founded in 1706 and became one of Maryland’s six Royal Ports of Entry during the colonial period. Positioned on the Chester River, it thrived as a trading hub, particularly for tobacco and wheat exports between approximately 1750 and 1790. The town's prosperity is deeply tied to maritime commerce, and its waterfront and commercial buildings reflect this economic history.

Beyond commerce, Chestertown played an important role in the American Revolution and early republic era. The town was the site of early protests against British policies, notably through events such as the Chestertown Tea Party, a local act of defiance inspired by the Boston Tea Party, reinforcing its patriotic legacy.

Architectural Significance

The district encompasses over 600 historic buildings, showcasing a rich variety of architectural styles, primarily Georgian, Federal, and Gothic Revival, with some Victorian influences evident in later 19th-century construction. This range provides a visual narrative of Chestertown’s development and the changing tastes of its residents over time.

Georgian Style: Characterized by symmetry, proportion, and classical details such as paneled doors, transom windows, and gabled roofs. This style is prominent in many of the district’s early 18th-century residences and public buildings.

Federal Style: Following Georgian architecture, Federal style buildings often feature more refined details such as elliptical fanlights, sidelights, and decorative cornices. This style became popular in the late 18th and early 19th centuries.

Gothic Revival: Represented mainly in the district’s ecclesiastical buildings, this style includes pointed arches, steeply pitched roofs, and decorative tracery, reflecting the religious architectural trends of the mid to late 19th century.

Notable Structures

Several buildings within the Chestertown Historic District stand out for their architectural merit and historical importance:

Hynson–Ringgold House (“The Abbey”): Built in 1767 by merchant Thomas Ringgold, this Georgian-style mansion is notable for its fine Chippendale-Georgian interior woodwork and is currently the official residence of the president of Washington College. Its elegance exemplifies colonial affluence and craftsmanship.

Denton House (also known as River House): Constructed around 1784 for merchant Richard Smyth, this three-story brick building exhibits a transitional style between Georgian and Federal architecture, featuring a raised basement and an elaborate Corinthian cornice. It served as a prominent merchant’s home, reflecting the wealth generated through trade.

Custom House: Dating to 1746, the Custom House was originally a combined warehouse and residence for Thomas Ringgold IV, a notable local attorney and merchant. This building played a key role in the town’s maritime trade operations. The property was later restored and entrusted to Washington College for preservation and adaptive use.

Widehall: Built circa 1770 by Thomas Smythe, this elegant residence is distinguished by its elaborate interior detailing and Georgian style. It is individually listed on the National Register of Historic Places and contributes significantly to the district’s historical narrative.

Kent County Courthouse: Constructed in 1865, this building symbolizes the civic and judicial development of Chestertown, incorporating Greek Revival elements and serving as a local landmark.

Chestertown Railroad Station: Built in 1902, this structure represents the town’s adaptation to transportation changes and economic shifts at the turn of the 20th century.

Preservation and Community Engagement

Chestertown has demonstrated a strong commitment to preserving its architectural heritage through active historic district regulations and community involvement. Property owners within the district are encouraged and sometimes required to follow preservation guidelines that maintain the historical character of buildings, particularly regarding external alterations.

The town also fosters community pride and cultural identity through various events that celebrate its history and heritage. Among the most notable is the annual Chestertown Tea Party Festival, a reenactment commemorating the town’s colonial resistance to British taxation on tea. This festival includes period costumes, educational programs, musical performances, and community gatherings, attracting both residents and tourists.

Visitor Experience

The Chestertown Historic District offers visitors a comprehensive experience combining history, architecture, and culture. Walking tours provide detailed insights into the stories behind individual buildings, prominent historical figures, and the town’s evolution from a colonial port to a modern community. The scenic waterfront and tree-lined streets are complemented by local shops, galleries, cafes, and restaurants that enhance the charm and hospitality of the area.

Washington College, located within the district, adds an academic and cultural dimension through its historic campus and support for preservation efforts.

Summary

The Chestertown Historic District stands as a testament to the historical, architectural, and cultural richness of Maryland’s Eastern Shore. Through its well-preserved collection of colonial, Federal, and Gothic Revival buildings, the district reflects the economic prosperity and social evolution of a town deeply connected to maritime trade and American history. Active preservation efforts, coupled with community engagement and educational programming, ensure that Chestertown remains a vibrant and living historic district, inviting visitors to experience a significant chapter of America’s past firsthand.