Discover the charm of Hope Boutique, your one-stop destination for timeless elegance and contemporary flair in Chester, MD. Located at 100 Piney Narrows Rd Unit C, we offer a carefully curated collection of stylish women's apparel, unique accessories, and captivating home goods that inspire joy and confidence. Whether you're searching for the perfect outfit to elevate your wardrobe, a distinctive piece to enliven your living space, or a thoughtful gift to delight a loved one, Hope Boutique promises an unparalleled shopping experience. Let our friendly and knowledgeable staff guide you through our exquisite selection, ensuring you leave with treasures you'll adore. Embrace the beauty and find your hope today at Hope Boutique. 

Hope Boutique

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

Discover the Dock House, nestled on the serene shores of Piney Narrows in Chester, MD. This quintessential waterfront restaurant blends rustic charm with modern comfort, providing a perfect escape from the everyday hustle. Savor stunning sunsets and picturesque views from our outdoor deck, perfect for relaxation or hosting memorable gatherings. Inside, enjoy a cozy, inviting atmosphere featuring elegant décor and top-notch amenities. Whether you're dining in or adventuring on the nearby waters, Dock House promises an experience like no other. Conveniently located at 110 Piney Narrows Rd, our restaurant is the perfect place to dine & relax, watch a game, or enjoy time with friends and family. 

Dock House

Discover the tranquil charm of Island View Marina, ideally situated at 1814 Crab Alley Dr, Chester, MD. Nestled along the picturesque Maryland shoreline, our premier marina offers pristine docking facilities, state-of-the-art amenities, and a warm, welcoming community for boating enthusiasts. Enjoy services such as secure docking, on-site maintenance, and easy access to the Chesapeake Bay, making it effortless to explore the region's natural beauty. Relax in our modern clubhouse, relish local seafood at nearby restaurants, or simply unwind with breathtaking sunsets over calm waters. Whether you're setting sail for adventure or seeking a serene getaway, Island View Marina is the perfect haven for your nautical lifestyle. Join us today and experience the unparalleled harmony of sea, sun, and service. 

Island View Marina

Experience the charm and beauty of the Eastern Shore at Kent Narrows Landing, located at 106 Piney Narrows Rd, Chester, MD 21619. Nestled along the picturesque waterfront, this premier destination combines serene natural surroundings with modern amenities. Perfect for weekend getaways, family gatherings, or business retreats, Kent Narrows Landing offers exceptional accommodations and stunning scenic views. Enjoy easy access to boating, fishing, and waterfront dining, as well as local attractions and charming boutique shops. With its welcoming atmosphere and convenient location, Kent Narrows Landing promises a memorable stay for leisure and adventure alike. Discover why Kent Narrows Landing is the perfect escape for those looking to unwind and explore the best of Maryland's Eastern Shore. Book your stay today! 

Kent Narrows Landing

Welcome to Little Creek Landing, Chester's premier waterfront community at Little Creek Rd, Chester, MD 21619. Nestled in a serene and picturesque environment, Little Creek Landing offers an unparalleled living experience. Our beautifully designed homes provide modern amenities and elegant finishes, perfectly complementing the natural beauty of the area. Enjoy stunning views, private boat slips, and an array of recreational activities like fishing, kayaking, and nature trails right at your doorstep. With easy access to nearby shops, dining, and top-rated schools, Little Creek Landing ensures a convenient and fulfilling lifestyle. Discover the perfect blend of tranquility and convenience at Little Creek Landing—where the charm of waterfront living meets the comforts of modern luxury. Your dream home awaits! 

Little Creek Landing

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 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

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

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

Cross Island Trail goes from Terrapin Nature Park on the shores of the Chesapeake Bay to the Kent Narrows Waterfront district, (Terrapin to Long Point Park). 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.   

Cross Island Trail

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