Nestled along the picturesque Chester River, The Sandbar at Rolph's Marina in Chestertown, Maryland, offers a vibrant and relaxed waterfront dining experience. Known for its impressive views and laid-back atmosphere, this spot is a favorite among both locals and visitors seeking to enjoy a meal with a stunning backdrop. The Sandbar serves a variety of fresh seafood dishes, capturing the essence of Maryland's culinary tradition with flavors that are sure to delight the palate.

Aimed at those who appreciate a casual dining environment, The Sandbar is perfect for families, friends, and tourists looking to enjoy a meal by the water. With its welcoming ambiance, it's easy to unwind here after a day of exploring or boating on the river. Guests can savor their meals while soaking in the beautiful river views, making it a memorable stop on any itinerary.

The Sandbar stands out for its commitment to quality and freshness, ensuring that every dish embodies the rich flavors of the region. Its location at Rolph's Marina makes it easily accessible by boat, adding an element of adventure to the dining experience. Whether you’re a local looking for a scenic dinner spot or a tourist in search of authentic Chesapeake Bay cuisine, The Sandbar at Rolph's Marina promises a delightful experience by the water's edge. 

The Sandbar At Rolph's Marina

Discover the alluring flavors of Asia at Cafe Sado, nestled at 870 High St, Chestertown, MD. Our menu is a delectable fusion of Japanese and Thai cuisines, offering everything from silky sushi to hearty noodle bowls. Enjoy a warm, inviting atmosphere that's perfect for a casual lunch, intimate dinner, or special celebration. Savor our fresh, locally sourced ingredients combined with authentic spices and innovative recipes. Our dedicated chefs and friendly staff ensure a memorable dining experience every time. Whether you're a sushi connoisseur or a fan of Thai curries, Cafe Sado is your go-to destination for exquisite Asian cuisine in Chestertown. Come taste the tradition and creativity—we promise you’ll leave craving more! 

Cafe Sado

Nestled in the heart of Church Hill, Maryland, Church Hill Theatre offers a captivating experience that showcases the vibrant local arts scene. The theater is renowned for its diverse repertoire of live performances, ranging from classic dramas to contemporary comedies and musicals. Its mission is to provide a platform for local talent as well as to enrich the community through artistic expression. 

Ideal for theater enthusiasts and casual visitors alike, Church Hill Theatre is committed to creating an engaging atmosphere where culture thrives. The intimate setting of the historic venue enhances the viewing experience, giving audiences a closer connection to the performances. This community-centric hub not only hosts a variety of plays but also organizes workshops and educational programs, making it an excellent destination for both entertainment and learning.

Church Hill Theatre stands out for its dedication to quality productions and its role as a cultural beacon in the region. Whether you're a local resident or a visitor exploring the charming town of Church Hill, stepping into this theater promises an unforgettable experience of creativity and community connection. With its blend of tradition and innovation, Church Hill Theatre invites you to be part of its ongoing narrative, where every performance brings the community a little closer together. 

Church Hill Theatre

Discover the charm of Bohemia Trading Company, nestled in the heart of historic Chestertown, MD at 7400 Church Hill Rd. Our unique boutique offers a curated selection of artisanal goods, handcrafted jewelry, vintage treasures, and distinctive home decor. Every item in our collection is carefully chosen to inspire and delight those with a love for eclectic elegance and timeless style. Whether you're in search of the perfect gift or a special piece to elevate your space, Bohemia Trading Company promises an enchanting shopping experience. Visit us today and explore a world where history meets creativity. 

Bohemia Trading Company

Discover The Mill of Kingstown, the premium destination for pet, livestock, and lawn care essentials, located at 7121 Church Hill Rd, Chestertown, MD. Renowned for our commitment to quality and community, we offer a vast selection of top-tier feeds, seeds, pet supplies, and farm equipment. Our knowledgeable team provides personalized service, ensuring you find exactly what your animals and garden need to thrive. With a rich history rooted in agriculture, The Mill of Kingstown is your trusted partner for expert advice and exceptional products. Join our loyal customers who count on The Mill for innovation, tradition, and superior care in every season. Experience the difference today—where local charm meets agricultural excellence. 

The Mill of Kingstown

Discover timeless elegance and unmatched quality at Chestertown Furniture Center, located at 6612 Church Hill Rd, Chestertown, MD 21620. Step into our welcoming showroom where you'll find a curated selection of stylish, high-quality furniture to transform every room in your home. From classic to contemporary, our wide range of sofas, dining sets, bedroom suites, and unique accent pieces cater to all tastes and styles. Our knowledgeable and friendly staff are dedicated to helping you create a space that truly reflects your personality and lifestyle. With exceptional customer service and unbeatable prices, Chestertown Furniture Center is your go-to destination for achieving the home of your dreams. Visit us today and experience the difference! 

Chestertown Furniture Center

Welcome to Milano's Pizzeria, where authentic Italian flavors meet the charm of Chestertown! Located at 6346 Church Hill Rd, our cozy eatery has become a beloved local gem. At Milano's, we pride ourselves on using the freshest ingredients to create mouthwatering pizzas, delectable pastas, and savory subs that are sure to satisfy every palate. Our expert chefs craft each dish with care, ensuring a delightful culinary experience in every bite. Whether you’re dining in, taking out, or getting delivery, Milano’s Pizzeria promises a warm atmosphere and exceptional service. Join us today and taste the tradition of Italy, right here in Chestertown. Buon Appetito! 

Milano's Pizzeria

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

Business Type

Has Promotions Available

Special Features