Discover the epitome of maritime luxury at Piney Narrows Yacht Haven, nestled in the heart of Chester, MD. Located at 500 Piney Narrows Rd, our premier marina offers world-class amenities and services for boating enthusiasts. Enjoy state-of-the-art floating dock systems, full-service fuel docks, and comprehensive maintenance facilities all set against the picturesque backdrop of the Chesapeake Bay. Relax in our captain’s lounge, make use of high-speed Wi-Fi, or take advantage of our on-site ship’s store for all your essential supplies. Ideal for both transient boaters and long-term slip holders, Piney Narrows Yacht Haven promises exceptional convenience with nearby dining, shopping, and entertainment options. Experience the perfect blend of adventure, comfort, and community at Piney Narrows Yacht Haven—where your nautical journey begins. 

Piney Narrows Yacht Haven

Nestled on the scenic Chesapeake Bay in Grasonville, Maryland, The Big Owl offers a vibrant and inviting atmosphere for locals and tourists alike. This waterfront establishment is the perfect spot to unwind with stunning views and enjoy the coastal charm the region is known for. Whether you're savoring fresh seafood or sipping a cold drink, The Big Owl delivers a memorable experience with its relaxed, breezy vibe.

The Big Owl is celebrated for its lively ambiance and warm hospitality, making it a popular gathering spot for groups looking to soak in some local flavor. Known for its tropical cocktails and delicious fare, this venue often features live music performances that complement the laid-back yet energetic environment. The restaurant is especially popular during the summer months when the outdoor deck becomes a focal point for patrons seeking a quintessential bayside experience.

Ideal for families, friend groups, or anyone wanting a taste of Maryland’s coastal lifestyle, The Big Owl is a destination that promises both fun and relaxation. Its prime location and friendly staff ensure that visitors of all ages can enjoy the sun, music, and the beautiful waterfront views. Whether you're a local or visiting from afar, The Big Owl is a delightful spot to indulge in the unique charm of the Chesapeake Bay area. 

The Big Owl

Experience the culinary charm of the Chesapeake Bay at The Narrows Restaurant, nestled at 3023 Kent Narrow Way S, Grasonville, MD. This waterfront gem combines breathtaking views with a tantalizing menu of fresh, local seafood and regional specialties. Enjoy a relaxed yet refined atmosphere perfect for any occasion, whether you're seeking a romantic dinner, a family celebration, or a casual lunch with friends. Savor our signature crab cakes, expertly prepared oysters, and daily chef specials, all crafted with the finest ingredients. Complement your meal with an exquisite selection from our wine and cocktail list. Join us at The Narrows for an unforgettable dining adventure where the flavors of Maryland come alive. 

The Narrows Restaurant

Discover the finest taste of Chesapeake Bay at Harris Crab House, located on the scenic shores of Kent Narrows in Grasonville, MD. Renowned for its warm, family-friendly atmosphere, Harris Crab House offers an unforgettable dining experience featuring the freshest seafood straight from local waters. Delight in our succulent Maryland blue crabs, expertly steamed and paired with mouthwatering sides. Our diverse menu, ocean-to-table ethos, and impeccable service make us a staple for locals and travelers alike. Whether you're unwinding with friends on our waterfront deck or enjoying a cozy family dinner, Harris Crab House is your go-to destination for authentic, flavorful seafood that captures the essence of Maryland's Eastern Shore. Join us at 433 Kent Narrow Way N, and savor the taste of tradition. 

Harris Crab House

Discover the vibrant charm of Red Eye's Dock Bar, the ultimate waterfront destination nestled at 428 Kent Narrow Way N, Grasonville, MD. Boasting breathtaking views of the bustling marina, this iconic venue offers a perfect blend of relaxation and entertainment. Savor mouthwatering seafood, refreshing cocktails, and local craft beers as you soak in the lively atmosphere. With live music, friendly service, and sunset vistas, Red Eye's Dock Bar is not just a place to eat—it's an experience. Whether you're docking your boat or driving in, make memories with friends and family at the Eastern Shore's premier dockside hangout. 

Red Eye's Dock Bar

Discover the ultimate seafood dining experience at Fisherman's Crab Deck in Grasonville, MD! Nestled along the picturesque Kent Narrows waterfront, our restaurant at 3032 Kent Narrow Way S offers a culinary haven for seafood enthusiasts. Indulge in freshly caught Maryland Blue Crabs, succulent oysters, and an array of other coastal delights, all prepared to perfection. With our spacious outdoor deck, you can savor your meal while basking in stunning views of the marina and serene waters. Whether you're enjoying a casual lunch, a lively dinner, or our famous crab feasts, Fisherman's Crab Deck promises an unforgettable experience. Come for the food, stay for the ambiance, and leave with cherished memories. Join us for a taste of Maryland's best seafood! 

Fisherman's Crab Deck

Nestled along the picturesque waterfront of Kent Narrows, Bridges Restaurant is your premier dining destination in Grasonville, MD. Located at 321 Wells Cove Rd, our establishment offers a sophisticated yet inviting atmosphere perfect for any occasion. Savor our innovative, locally-sourced cuisine, featuring fresh seafood, succulent steaks, and creative, seasonal dishes that highlight the bounty of the Chesapeake Bay. Enjoy stunning panoramic views from our expansive outdoor patio or relax in our elegant indoor dining space. Whether you're indulging in a romantic dinner, hosting a special event, or enjoying happy hour with friends, Bridges Restaurant promises an unforgettable experience enhanced by attentive service and a meticulously curated wine and cocktail menu. Discover why Bridges is a beloved gem in the heart of Kent Narrows. 

Bridges Restaurant on Kent Narrows

Nestled in the charming town of Grasonville, Maryland, Fisherman's Inn Restaurant offers a delightful experience for lovers of fresh seafood and traditional American cuisine. Situated at 3116 Main Street, this iconic dining destination has been serving locals and visitors since its establishment. With its beautiful waterfront location, guests can enjoy picturesque views of the Chesapeake Bay while savoring meticulously prepared dishes.

Fisherman’s Inn is renowned for its inviting ambiance and commitment to quality, drawing food enthusiasts who enjoy hearty fare in a relaxed setting. The menu features a wide array of seafood delicacies, including the freshest catches from the bay, alongside other classic American favorites. Whether you're craving Maryland's famous crab cakes, succulent oysters, or a perfectly grilled steak, there’s something to satisfy every palate.

This family-friendly restaurant caters to all age groups, making it an ideal spot for gatherings and celebrations. Its location and scenic views also make it a popular choice for tourists wanting to experience a taste of Maryland’s coastal charm. While enjoying the delicious offerings, guests are treated to warm hospitality and efficient service, enhancing the dining experience.

Fisherman’s Inn Restaurant stands out for its deep-rooted tradition, exceptional food, and the sense of community it fosters among guests. Whether you’re a local resident or a traveler passing through, this restaurant promises a memorable meal rooted in the rich flavors of the Chesapeake region. 

Fisherman's Inn Restaurant

Welcome to Safe Harbor Narrows Point, an exclusive marina destination nestled at 428 Kent Narrow Way N in picturesque Grasonville, MD. Designed for the discerning boater, our state-of-the-art facilities provide an unparalleled experience on Maryland's stunning Eastern Shore. Unwind with premium amenities including secure, deep-water slips, pristine bathhouses, and a fully-equipped service center for all your maritime needs. Enjoy direct access to rich fishing grounds and scenic cruising routes, while nearby exceptional dining and entertainment options await to complement your voyage. Safe Harbor Narrows Point is where luxury meets adventure, offering a sophisticated haven for your vessel and a serene retreat for you. Join us and discover the perfect blend of coastal charm and modern convenience. 

Safe Harbor Narrows Point

Discover a waterfront paradise at The Jetty, located at 201 Wells Cove Rd, Grasonville, MD. Nestled along the serene shores of the Chesapeake Bay, The Jetty offers an unparalleled dining and entertainment experience. Savor fresh seafood and local favorites, expertly crafted to tantalize your taste buds, all while enjoying breathtaking views of the bay. Our lively venue features live music, cool cocktails, and a vibrant atmosphere perfect for gatherings with friends or family. Whether you're unwinding after a day on the water, attending one of our signature events, or simply soaking up the sun on our expansive deck, The Jetty promises an unforgettable time. Come spend a day where the food is fresh, the music is lively, and the views are always spectacular. Make memories that last at The Jetty – the beating heart of Grasonville's waterfront. 

The Jetty

South Island Trail goes from Matapeake State Park to Romancoke Fishing Pier. The trail affords pedestrians’ runners and cyclist unique opportunities and has been home to many races, which we can highlight some in our event schedule I spoke about including below.   

South Island Trail

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