Nestled in the heart of Annapolis, DARK HORSE offers an inviting escape for coffee enthusiasts and casual diners alike. Conveniently located on Bay Ridge Road, this charming establishment is celebrated for its distinctive blend of artisanal coffee and relaxed ambiance. Whether you're a local resident searching for your new favorite brew or a visitor looking to start your Annapolis adventure with a caffeine kick, DARK HORSE promises a memorable experience. With a commitment to quality, they serve freshly brewed coffee made from high-quality beans, ensuring each cup is a perfect blend of flavor and aroma.

Guests can enjoy their beverages in a cozy, welcoming environment, making it an ideal spot for catching up with friends or finding a quiet corner for some personal time. Settle in with a good book, or bring your laptop to work or study while sipping on your favorite coffee concoction. While the specific menu selection may vary, you can anticipate a variety of options catering to diverse palates. 

A favorite among Annapolis locals and visitors, DARK HORSE stands out for its dedication to providing a warm, community-driven atmosphere. Whether you're grabbing a quick coffee on the go or looking for a comfortable place to unwind, DARK HORSE is a must-visit spot that captures the essence of local charm and hospitality in Annapolis. 

Dark Horse Annapolis

Nestled in the charming city of Annapolis, Grump's Cafe offers a delightful dining experience that captures the spirit of local hospitality. Conveniently located at 117 Hillsmere Drive, this beloved cafe is a go-to spot for both locals and visitors seeking a taste of hearty, American-inspired cuisine in a relaxed setting. Known for its warm and inviting atmosphere, Grump's Cafe provides a welcoming escape, where customers can enjoy a variety of freshly prepared dishes.

The menu features a diverse range of breakfast and lunch options, catering to a wide array of tastes and preferences. Whether you’re in the mood for a classic eggs-and-bacon breakfast, a sandwich, or a freshly baked pastry, Grump's Cafe has something to satisfy every craving. The cafe's commitment to quality ingredients ensures each meal is a delight to the senses.

Perfect for families, friends, or solo diners seeking a cozy retreat, Grump's Cafe stands out for its attentive service and charming ambiance. The friendly staff and laid-back vibe make it an excellent choice for casual dining, while the convenient location attracts a steady stream of regular patrons and newcomers alike. Whether you're starting your day with a delicious breakfast or catching up with friends over lunch, Grump's Cafe is a must-visit destination that embodies the casual charm of Annapolis. 

Grump's Cafe

Experience a vibrant slice of Latin America at Caliente Grill, located at 907 Bay Ridge Rd in the heart of Annapolis, MD. Known for its lively atmosphere and authentic flavors, this locally cherished spot brings the culinary richness of Latin cuisine to your table. Delight in a menu that features classic dishes such as tacos, burritos, and a selection of tantalizing grilled meats, each prepared with a perfect blend of spices that evoke the warmth of traditional Latin kitchens.

Caliente Grill is a haven for food enthusiasts who appreciate a meal that tells a story of culture and heritage. Whether you're a family seeking a friendly dining experience or a group of friends looking to indulge in bold flavors, this restaurant offers something for everyone. The welcoming staff and vibrant decor create a space where guests can relax and enjoy the lively energy that the restaurant is known for.

Come for the food, stay for the experience, and take with you a memory of Annapolis seasoned with the zest of Latin flair. For anyone seeking the authenticity of a true Latin grill, Caliente Grill is a must-visit destination. 

Caliente Grill

Rita's Italian Ice & Frozen Custard in Annapolis, MD, is a delightful destination for dessert lovers of all ages. Known for its vibrant and refreshing Italian ice, Rita's offers a wide variety of flavors that change daily, ensuring repeat visits never dull. Alongside their Italian ice, they serve creamy frozen custard, creating the perfect combination of smooth and icy treats. Whether you're looking for a quick snack or a sweet ending to a day out, Rita's has something to satisfy your cravings.

Located at 911 Bay Ridge Rd, this charming spot is popular among locals and visitors alike, making it a great place to stop and enjoy a moment of indulgence. The friendly atmosphere and prompt service add to the experience, encouraging people to come back again and again. Rita's is perfect for families seeking a fun treat, groups enjoying an outing, or individuals in search of a delicious pick-me-up. With options plentiful and delicious, Rita's Italian Ice & Frozen Custard invites you to cool down and enjoy a classic taste of summer any time of the year. 

Rita's Italian Ice & Frozen Custard

Nestled in the serene landscapes of Annapolis, Maryland, Great Frogs Winery offers a remarkable experience for wine enthusiasts and casual visitors alike. Located at 3218 Harness Creek Road, this charming winery is known for its rustic charm and the rich history that comes with it. Originally established on a historic tobacco farm, Great Frogs Winery brings a touch of local history into every bottle, crafting wines that reflect the unique terroir of the region.

Great Frogs Winery primarily caters to adults looking to explore sophisticated wines in a relaxed, welcoming atmosphere. Visitors can indulge in a range of handcrafted wines that showcase the best of locally grown grapes. Whether you're a connoisseur or just beginning your wine journey, the knowledgeable staff is eager to guide you through tastings that highlight the winery's commitment to quality and flavor.

The laid-back, bucolic setting of Great Frogs Winery makes it an ideal destination for couples, friends, or small groups seeking a peaceful retreat from city life. The winery’s dedication to sustainability and local sourcing further enhances its appeal, allowing guests to appreciate not just the wines, but the ethos behind their creation. While the tasting experiences are the highlight, visitors may also enjoy the serene surroundings that provide a perfect backdrop for a relaxing day out.

Whether you're visiting Annapolis or a local resident, Great Frogs Winery offers an authentic taste of Maryland's burgeoning wine scene in a charming and inviting setting. 

Great Frogs Winery

Discover the delightful tastes of Jack's Fortune, a Chinese restaurant nestled in the charming city of Annapolis, Maryland. Located at 960 Bay Ridge Road, Jack's Fortune offers a diverse menu featuring authentic Chinese cuisine, catering to both locals and tourists seeking a flavorful dining experience. Guests can savor traditional dishes ranging from savory stir-fries and aromatic noodle bowls to succulent seafood options, all crafted with fresh ingredients and authentic Chinese spices.

The ambiance at Jack's Fortune is warm and inviting, making it an ideal venue for a relaxed meal with family or friends. Its appealing decor and welcoming service contribute to a comfortable dining atmosphere. While it's a favorite among locals, Jack's Fortune also attracts visitors keen to explore the culinary offerings of Annapolis.

Jack's Fortune is an excellent choice for those who appreciate genuine Chinese flavors and are looking for a casual yet satisfying dining option. Whether you're a long-time resident or a newcomer exploring Annapolis’s diverse food scene, this establishment promises a memorable meal that captures the essence of Chinese cuisine. Visit Jack's Fortune for a delightful escape to China right in the heart of Annapolis. 

Jack's Fortune

Discover the distinctive flavors of Annapolis at the Annapolis Smokehouse and Tavern, located at 107 Hillsmere Dr. This local gem is known for its mouthwatering menu that caters to barbecue aficionados and casual diners alike. Specializing in hearty smoked meats and homemade sides, the tavern offers a taste experience that stays true to authentic BBQ traditions. From tender ribs and succulent pulled pork to savory brisket, each dish is crafted with care, making it a must-visit for those who relish rich and smoky flavors.

Annapolis Smokehouse and Tavern welcomes families and groups with its relaxed and friendly atmosphere, perfect for gatherings and casual evenings out. It’s a popular spot among locals and visitors seeking a taste of Maryland hospitality coupled with great food. The tavern also provides a selection of craft beers and specialty cocktails, allowing patrons to unwind and enjoy a complete dining experience.

Whether you're a local resident or passing through Annapolis, this tavern offers an inviting setting to indulge in classic barbecue cuisine. With its commitment to quality and flavor, Annapolis Smokehouse and Tavern stands out as a true culinary destination in the area. 

Annapolis Smokehouse And Tavern

Taqueria Juquilita, located at 126 Hillsmere Drive in the heart of Annapolis, Maryland, offers a genuine taste of traditional Mexican cuisine that delights both locals and visitors. Known for its authentic flavors, this taqueria serves a variety of classic Mexican dishes that transport diners straight to the vibrant streets of Mexico. From expertly seasoned tacos to flavorful burritos, the menu boasts a range of options that cater to those seeking an authentic culinary experience.

Whether you're a local resident craving the comforting taste of home-style Mexican cooking or a traveler exploring Annapolis's diverse food scene, Taqueria Juquilita provides a welcoming atmosphere complemented by friendly service. The inviting space is perfect for casual dinners with friends or a relaxed meal after a day of touring the nearby attractions.

Renowned for its commitment to high-quality ingredients and traditional recipes, Taqueria Juquilita has become a staple stop for anyone eager to indulge in the rich, savory delights of Mexican cuisine. While specific features such as kid-friendly or gluten-sensitive options aren't confirmed, the taqueria's reputation for authenticity and hospitality makes it a must-visit destination for food lovers of all ages. Experience the flavors of Mexico in the charming setting of Annapolis at Taqueria Juquilita—where every meal is a celebration of taste, culture, and community. 

Taqueria Juquilita

Nestled in the heart of Annapolis, Rocco's Pizzeria offers an authentic taste of Italy right on Bay Ridge Road. This popular local eatery is known for its delicious, hand-tossed pizzas made with fresh, high-quality ingredients. Whether you're a local resident or just visiting, Rocco's provides a delightful dining experience perfect for casual hangouts or family dinners. The warm and inviting atmosphere of the pizzeria makes it an excellent place for spending quality time with friends and loved ones.

Rocco's Pizzeria caters to a wide audience, from families with kids to groups of friends seeking a relaxed meal. The menu not only features a variety of pizza options but also includes classic Italian dishes, making it a versatile spot for those craving comforting, familiar flavors. The staff at Rocco's is friendly and attentive, ensuring a pleasant visit for every guest.

What sets Rocco's apart is its commitment to delivering an authentic Italian experience right in Annapolis, combining traditional recipes with a welcoming, local charm. Whether you're in the mood for a quick slice or a full Italian feast, Rocco's Pizzeria is a must-visit destination for anyone passionate about good food and great company. 

Rocco's Pizzeria

Discover Main & Market Catering, Cafe and Bakery, a delightful culinary destination nestled in the heart of Annapolis, Maryland. Located at 914 Bay Ridge Road, this charming venue offers a diverse array of delicious offerings, expertly catering to both local patrons and visitors alike. Main & Market is renowned for its fresh, innovative dishes and artisanal baked goods, all crafted in-house with the utmost care and culinary finesse.

Step into the inviting cafe and savor a menu that celebrates a fusion of classic and contemporary flavors. Whether you're stopping by for a comforting breakfast, a satisfying lunch, or a cozy evening meal, the cafe's offerings cater to a wide range of tastes. The bakery is a haven for lovers of sweet and savory delights, featuring everything from freshly baked bread to delectable pastries and desserts that are perfect for any occasion.

Main & Market also excels in catering services, bringing their culinary expertise to your special events. Known for their personalized service and attention to detail, the catering team works closely with clients to create memorable experiences that are both delicious and seamlessly tailored to individual needs.

Whether you're a local resident, a tourist exploring Annapolis, or planning an event, Main & Market Catering, Cafe and Bakery invites you to indulge in a culinary adventure you won't soon forget. Enjoy the warm atmosphere, friendly service, and exquisite food that make this establishment a true gem in the community. 

Main & Market Catering, Cafe and Bakery

The Key School is an independent coeducational school, located in the neighborhood of Hillsmere Shores in Annapolis, Maryland. The Key School was established by a group of tutors from St. John's College in 1958. Key is a member of the National Association of Independent Schools.

State of the art facility that includes
2 full size indoor courts (hardwood)
2 full size grass fields (all sports)

Key School

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