Nestled on the south side of Spa Creek, just a short stroll over the iconic Eastport Bridge from historic downtown Annapolis, sits a neighborhood that pulses with nautical pride, community spirit, and a rich heritage: Eastport. What was once a humble, independent working-class district is now one of Annapolis’s most cherished corners, blending its deep-rooted maritime past with a vibrant present-day culture. Let’s journey through time and explore what makes Eastport such a special place to residents and visitors alike.
Origins: A Village by the Water
Eastport was born out of necessity and geography. In the 19th century, Annapolis was booming as Maryland’s capital and a bustling port, but the land across Spa Creek remained rural and lightly developed. In 1868, a group of entrepreneurs founded the Eastport Peninsula Company to create a new community—one anchored, quite literally, by the water. The plots along Fourth Street, Chester Avenue, and Severn Avenue were quickly snapped up, and a grid of streets sprang to life, soon populated by shipbuilders, watermen, and their families.
The neighborhood’s name, “Eastport,” reflected its position at the eastern gateway to Annapolis’s port. It was a practical name but soon became synonymous with a scrappy, can-do community identity.
Defining Historical Milestones
Eastport has experienced milestones that shaped its character and ensured its legacy:
- Annexation Battles and Independence: For many years, Eastport operated as an independent village—not officially a neighborhood of Annapolis until 1951. Residents fiercely valued their autonomy. Even today, the annual “Eastport vs. Annapolis Tug of War” playfully commemorates this once-contentious relationship, with spirited teams pulling opposite ends of a rope across Spa Creek.
- Growth of Maritime Industry: By the late 19th and early 20th centuries, Eastport flourished as a maritime hub. The Annapolis Glass Works on State Street and a web of boatyards supported both employment and innovation. It was common to see skipjacks, crab shanties, and oyster boats along the waterfront. Streets like Severn Avenue and Second Street were lined with the homes of shipwrights and sailors.
- Naval Academy’s Influence: Eastport’s proximity to the U.S. Naval Academy across the creek brought a steady flow of midshipmen, retirees, and military families into the neighborhood, weaving patriotism and service into the local culture. Many homes on Chesapeake Avenue and Back Creek overlook Navy vessels gliding by, linking generations of residents to Annapolis’s defense legacy.
Notable Landmarks and Beloved Buildings
Eastport’s unique character shines through its landmarks—some steeped in history, others anchors of community life today.
- Eastport Yacht Club (EYC): Founded in 1980, the club is younger than some might guess, yet it quickly became synonymous with Eastport’s maritime identity. EYC on Second Street is not just a club; its events, like the annual Lights Parade and Boatyard Bar & Grill Regatta, are staples in the local calendar.
- Davis’ Pub: Located on Chester Avenue, this neighborhood watering hole began as a grocery in the early 1900s and became a beloved pub and gathering place. Its weathered sign and cozy charm make it a true Eastport icon.
- St. Luke's Episcopal Church: Set on Spa Road, the church helped anchor Eastport’s spiritual and social life from its founding in 1868. The surrounding parish hall often buzzes with community activities and outreach.
- M Street Park and Horn Point: At the far eastern tip of the peninsula, Horn Point offers panoramic views of the Annapolis harbor and the Chesapeake Bay. The tiny M Street Park is a locals’ favorite—a leafy oasis tucked into the neighborhood grid, perfect for picnics or a quiet sunset.
- Maritime Museum of Annapolis: Housed in the restored McNasby Oyster Company packing plant along Second Street, this museum keeps Eastport’s working waterfront legacy alive. Visitors glimpse the neighborhood’s oystering past, learn about Bay ecology, and participate in festivals like the annual Oyster Roast.
The Evolution of Eastport: Character Endures Through Change
Like many waterfront neighborhoods on the East Coast, Eastport has evolved dramatically over the decades—but its heart remains intact.
- 1970s–1980s: Bohemian Spirit: While some traditional industries faded, Eastport attracted artists, boatbuilders, and free spirits drawn to waterfront living and an “island” vibe. Rowhouses and cottages along Third and Fifth Streets were lovingly restored by creative newcomers, ensuring Eastport’s charm didn’t fade with the shipyards.
- Community Advocacy: In the late 1990s, Eastport residents famously “seceded” from Annapolis for a tongue-in-cheek Independence Day, reinforcing the local sense of humor and fierce pride. The neighborhood association actively promotes “The Maritime Republic of Eastport,” a playful but passionate campaign for celebrating uniqueness.
- Today: A Vibrant Melting Pot: Eastport is now one of Annapolis’s most sought-after places to live, known for its hospitality, walkable streets, and welcoming spirit. Chesapeake Avenue rounds the peninsula like a horseshoe, connecting generations of families—lifelong locals and newcomers alike. The rise of sailing schools, family-owned seafood restaurants, and the lure of waterfront festivals ensure Eastport’s energy and legacy endure.
What Makes Eastport Special?
Ask any longtime Eastport resident, and you’ll hear stories that reach far beyond physical landmarks. It’s the neighbor who always keeps an eye out. It’s the twilight sight of sailboats bobbing at Horn Point. It’s a crab feast on a front porch along Severn Avenue or a child’s first bluefish off the dock at Back Creek. Here, tradition and togetherness are as sturdy and essential as the pilings along the waterfront.
Eastport is a neighborhood where history isn’t just a backdrop—it’s an ongoing story, written by everyone who has called this peninsula home. From humble beginnings to harbor-front haven, Eastport’s tale is one of resilience, pride, and unmistakable charm.