Eastport Historic District | Annapolis

The Eastport Historic District is a distinctive, waterfront neighborhood in Annapolis, Maryland, located directly across the Spa Creek from the city’s historic downtown. Once an independent town (until its annexation by Annapolis in 1951), Eastport retains its unique identity and maritime character, shaped by generations of watermen, boatbuilders, and seafarers. Today, it blends rich history, nautical tradition, residential charm, and modern vitality in a compact, walkable setting.

Historical Overview

Eastport began developing in earnest in the late 19th century, though it had long been a peninsula inhabited by Native Americans and used for agriculture by early European settlers. Its location between Spa Creek and Back Creek-with easy access to the Severn River and the Chesapeake Bay-made it a natural center for boatbuilding, fishing, and oystering.

By the 1880s and 1890s, the area had developed into a working-class maritime community. Many of its original residents were craftsmen, shipwrights, and oystermen who supported the growing commercial and naval needs of Annapolis. Modest Victorian cottages, frame duplexes, and two-story rowhouses sprang up quickly, forming the core of Eastport’s residential architecture.

Architectural Character

The Eastport Historic District contains a wide variety of architectural styles that reflect its development timeline and working-class origins. Notable features include:

Folk Victorian and Queen Anne cottages with gabled roofs, decorative brackets, and wide porches.

Colonial Revival and Craftsman-style bungalows, especially in areas built during the early 20th century.

Rows of vernacular two-story homes, often built side-by-side or as duplexes for watermen and their families.

Industrial maritime buildings, such as former boatyards and marine supply stores, now converted into restaurants, galleries, or boat-related businesses.

Many homes feature narrow lots, rear outbuildings, and gardens, emphasizing utility and compact design. Despite increasing development, the district retains its original scale and orientation, with narrow streets like Second Street, Chester Avenue, and Severn Avenue still aligned to the shoreline.

Maritime Industry and Legacy

The district’s most defining feature is its deep connection to the Chesapeake Bay and the maritime trades. Historically, Eastport housed several small-scale boatyards and sail lofts that served both the commercial and leisure boating industries.

Today, that legacy continues with:

Numerous marinas, yacht clubs, and marine service businesses.

Headquarters for maritime education institutions like the Annapolis Maritime Museum & Park (in the former McNasby Oyster Company building).

Sailing schools, including the Eastport Yacht Club, which trains new sailors and hosts races.

The presence of boats docked along the creeks, seafood restaurants perched over the water, and marine supply shops all reinforce Eastport’s strong seafaring identity.

Community Culture and Events

Though annexed in 1951, Eastport proudly maintains its own distinct character. Locals often refer to it jokingly as the "Maritime Republic of Eastport", a tongue-in-cheek "secession" movement created in 1998 as a satirical protest of the temporary closure of the Spa Creek Bridge. This playful spirit has led to a variety of quirky, community-driven events, including:

The Tug of War Across the Creek: An annual competition between Eastport and downtown Annapolis teams pulling on a rope spanning Spa Creek.

Eastport-a-Rockin’: A local music and arts festival showcasing regional talent and food vendors.

Lights Parade Viewing: Eastport’s waterfront makes it an ideal vantage point for viewing Annapolis’s annual holiday boat parade.

The neighborhood’s culture is welcoming, artistic, and unpretentious, with an emphasis on local pride and communal spirit.

Modern Life in a Historic Setting

Eastport today blends its historical roots with modern residential and commercial development. Key modern features include:

A growing number of restaurants, art galleries, and boutique shops, especially along Severn Avenue and Fourth Street.

Cafés and brewpubs located in renovated boatyards or along the water.

An active residential community, with a mix of original homes and newer infill construction that generally respects the district’s architectural scale.

Scenic walking and biking opportunities along the waterfront and Spa Creek’s edge.

Boundaries and Layout

The Eastport Historic District is bordered by:

Spa Creek to the north (across from downtown Annapolis)

Chesapeake Avenue to the south

Severn River and Back Creek on the eastern and western sides

It includes most of the area developed from the late 19th century through the 1940s. Streets are arranged in a grid, with low-rise residential housing dominating the inner streets and marine-related businesses closer to the water.

Preservation and Recognition

While the district has not been federally listed on the National Register of Historic Places as a separate designation, many of its structures are considered contributing elements to Annapolis’s broader cultural and architectural history. Preservation efforts are supported by local advocacy, zoning regulations, and community awareness.

Conclusion

The Eastport Historic District is a vibrant and deeply rooted maritime neighborhood that embodies the working-class heritage, architectural charm, and nautical soul of Annapolis. Its narrow streets, historic homes, and working waterfront evoke a slower, more authentic pace of life, while its modern energy-fueled by art, food, and music-keeps it lively and engaging. For visitors and locals alike, Eastport offers a dynamic blend of tradition and contemporary coastal living, all set against the backdrop of the Chesapeake Bay.