A Locals Guide To Living In Eastport, Maryland

Nestled just a short distance away from the bustling City Dock in Downtown Annapolis, the community of Eastport beckons with its unique blend of laid-back charm and picturesque waterfront. Crossing the iconic Spa Creek Bridge is your gateway to a community that boasts some of the most breathtaking water views in Annapolis, including captivating glimpses of the United States Naval Academy. Eastport, a tight-knit enclave, offers a haven for those seeking a vibrant yet tranquil lifestyle that's in close proximity to downtown excitement while remaining comfortably distant from the tourist throngs.

The allure of Eastport is deeply intertwined with its location on a narrow peninsula between the serenely flowing Spa Creek and Back Creek. These waterways converge and meander into the expansive Severn River, eventually leading the way to the illustrious Chesapeake Bay. This unique geography endows Eastport with an unparalleled relationship with the water, fostering a maritime spirit that resonates throughout the community.

Eastport Maritime Lifestyle and Nautical Heritage

Exploring along the streets in Eastport provides a delightful opportunity to savor the beauty of the water and admire historic architecture.  The town's charm is best experienced at a leisurely pace, allowing you to absorb its character and connect with the local community.

Standing proudly at the tip of the peninsula, the Annapolis Maritime Museum is a focal point for exploring the maritime heritage of the region. The Annapolis Maritime Museum is open to the public and visitors can purchase tickets in advance or at the door. There are interactive exhibits and guided tours available, so visitors can dive into the rich history of the Chesapeake Bay. Tours for groups are offered at special rates and are led by trained docents. For those seeking to connect with the bay up close, the museum serves as a gateway to boat tours that unravel the mysteries of the Chesapeake. Wilma Lee, a vintage Skipjack SailBoat, offers private and public tours.

Eastport offers more than just a view of the water – it invites you to be part of it. Numerous marinas dot the shoreline, offering opportunities to explore the Chesapeake Bay by boat or kayak. Annapolis Canoe and Kayak provides an avenue for the adventurous to paddle through the bay's tranquil waters, while Annapolis Electric Boat Rentals offers a more laid-back experience, allowing you to effortlessly navigate the bay's beauty without lifting a paddle. Whether you choose to partake in guided tours, paddle at your own pace, or simply bask in the waterfront atmosphere, Eastport's maritime offerings are sure to captivate and inspire.

Recommended Restaurants and Eateries

Aside from its charming streets to its breathtaking water views, Eastport offers residents a unique and welcoming atmosphere. One of the many highlights of this neighborhood is its exceptional dining and shopping scene showcasing the best that this charming community has to offer.

Carrol's Creek Cafe Located at 410 Severn Avenue, Carrol's Creek Cafe is an Eastport gem and is known for its elegant waterfront dining. With a focus on fresh seafood and locally sourced ingredients, this restaurant offers a diverse menu that caters to a wide range of palates. Whether you're craving a delectable crab cake, a succulent steak, or a vegetarian delight, Carrol's Creek Cafe has something for everyone. 

Chart House The neighboring Chart House, located at 300 2nd Street, is a must-visit dining destination for Eastport residents. Overlooking Spa Creek, this upscale restaurant offers stunning views and an innovative menu that showcases the best of Chesapeake Bay cuisine. From fresh seafood to prime rib, Chart House delivers an unforgettable dining experience. 

Boatyard Bar & Grill located at 400 4th Street The Boatyard Bar & Grill, with its nautical-themed decor and laid-back vibe, captures the essence of Eastport living. Known for its seafood-centric menu, including the famous crab cakes, this restaurant offers a taste of the Chesapeake Bay's culinary delights. Enjoy a casual meal on the outdoor patio or soak in the maritime atmosphere indoors.

Iron Rooster located in the heart of historic Annapolis, is a breakfast and brunch haven. From mouth watering pancakes to creative twists on classic breakfast dishes, Iron Rooster serves up comfort food with a gourmet touch. If you're a fan of all-day breakfast and inventive cocktails, this eatery is a must-visit.

Harper's Waterfront Located at 400 Chester Avenue, Harper's Waterfront offers a unique dining experience with its waterfront views and contemporary American cuisine. Indulge in seasonal dishes that highlight local ingredients, and sip on craft cocktails while watching the boats go by. Whether you're celebrating a special occasion or simply enjoying a leisurely meal, Harper's Waterfront delivers a memorable experience.

In addition to its gastronomic pleasures, Eastport also boasts delightful shopping destinations.  There are some wonderful boutique and antique shops or you can easily access nearby shopping centers in downtown Annapolis, including the Historic District and the West Annapolis area. These areas feature a variety of boutiques, galleries, and specialty stores where you can explore local crafts, fashion, art, and more.


Residents of Eastport can find a variety of essential services and amenities at the local shopping center. Some of the offerings include the Eastport Kitchen for dining options, Annapolis Barber Shop for grooming needs, Eastport Liquors for beverages, and the Annapolis Athletic Club for fitness activities. Additionally, on weekends, residents can enjoy shopping for fresh produce and goods at the local farmers market held in the shopping center's parking lot.

Here are the other shopping malls that you may want to check out. 

Annapolis Towne Center is a thriving open-air shopping complex located just a short drive from Eastport. This shopping destination provides a blend of upscale and casual shopping, dining, and entertainment options. Here, you'll find popular brands like Whole Foods Market, and Target, as well as boutique shops, fitness centers, and a variety of restaurants. Whether you're looking for the latest fashion trends, gourmet groceries, or a cozy spot to enjoy a meal, Annapolis Towne Center has something for everyone. 

Another one is Westfield Annapolis Mall. It is a premier shopping destination that offers a diverse range of high-end fashion, electronics, home goods, and dining options. With more than 200 stores, including anchor tenants like Nordstrom, Macy's, and Apple, the mall is a paradise for shoppers seeking renowned brands and a comfortable indoor shopping experience. Alongside shopping, the mall features a food court and numerous restaurants, making it an excellent spot for a full day of retail therapy and dining

Historic Downtown Annapolis For those who appreciate historic charm and unique boutiques, a visit to Historic Downtown Annapolis is a must. Just a stone's throw away from Eastport, this enchanting district features cobblestone streets lined with boutique shops, art galleries, and specialty stores. Discover handmade jewelry, antiques, nautical-themed gifts, and much more while taking in the scenic beauty of the city's historic architecture. Don't forget to explore the historic landmarks, including the Maryland State House and the United States Naval Academy.

Maritime Republic of Eastport While not a traditional shopping center, the Maritime Republic of Eastport deserves a special mention for its unique shopping experiences. This vibrant and artistic community hosts various events throughout the year, including the annual "Eastport-a-Rockin'" music festival and the "Tug of War" across Spa Creek. These events often feature local artisans and vendors selling handmade crafts, artwork, and Eastport-themed merchandise. Keep an eye out for these community events to discover one-of-a-kind treasures that celebrate Eastport's maritime culture.

Eastport’s Proximity to Annapolis

One of the most significant advantages of living in Eastport is its close proximity to Annapolis. This geographical advantage means that residents of Eastport have easy access to all the amenities that Annapolis has to offer. Annapolis boasts a vibrant cultural scene, with theaters, art galleries, and museums, all just a short drive from Eastport. Whether you're in the mood for a night at the theater or want to explore the local art scene, Annapolis is steeped in history, and Eastport residents can effortlessly immerse themselves in this rich heritage where you can explore colonial-era buildings, visit the Maryland State House, and learn about the city's pivotal role in American history. The Naval Academy, a cornerstone of Annapolis, also offers guided tours and events that provide a unique glimpse into the life of midshipmen and the history of the U.S. Navy.

For those who love the outdoors, Eastport provides easy access to a range of recreational activities. The nearby Chesapeake Bay offers opportunities for boating, fishing, and water sports. Residents can take a leisurely stroll along the scenic waterfront or spend a day at nearby parks like Quiet Waters Park, which features hiking trails, picnicking areas, and even ice skating in the winter. The abundance of green spaces and waterways makes Eastport an outdoor enthusiast's paradise.

Eastport's strategic location ensures a seamless commute to Annapolis and beyond. Annapolis is connected to major highways, including Route 50, making it easy to reach neighboring cities like Baltimore and Washington, D.C. The city also offers reliable public transportation options, including buses and the Annapolis Transit Trolley, allowing residents to navigate the city without the need for a car.

Waterfront Real Estate and Quaint Residences: Eastport's Housing Scene

Eastport is a charming maritime community that offers a unique blend of history, natural beauty, and modern living. Known for its stunning waterfront views, maritime heritage, and a vibrant arts scene, Eastport has become an attractive destination for those seeking a blend of coastal living and urban convenience. 

One of the standout features of Eastport's housing scene is the abundance of historic and waterfront homes that dot its tree-lined streets. Many of these homes date back to the 19th century and have been meticulously preserved, showcasing the rich architectural heritage of the region. These homes range from charming colonial-style cottages to grand Victorian estates, each with its own story to tell. Bay Ridge, one of Eastport's prestigious neighborhoods, is renowned for its historic waterfront homes, offering stunning views of the Chesapeake Bay. It provides a glimpse into the area's maritime past while providing residents with luxurious living options.

For those seeking a more contemporary and low-maintenance lifestyle, Eastport also offers a range of modern waterfront condos. These condominium developments have sprung up along the shoreline, providing residents with a blend of luxury, convenience, and waterfront living. These properties often feature sleek designs, spacious layouts, and amenities such as private piers, boat slips, and rooftop terraces with panoramic views. Shearwater, a modern waterfront condominium community, epitomizes waterfront living with its contemporary design and stunning water views. 

Eastport's Maryland waterfront real estate scene is a captivating blend of history and modernity, offering a wide range of housing options to suit various preferences. Whether you're drawn to the charm of a historic home in the Historic Eastport district, the luxury of modern waterfront, or the convenience of contemporary condos, Eastport caters to a diverse range of residents. 

Can you see yourself living in Eastport Maryland? If you're on the hunt for your ideal home in Eastport, Contact Caprika Realty to connect with a real estate agent specialized in Eastport properties and its neighboring cities.


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