Deale, Maryland

Exploring Deale, Maryland: A Charming Getaway for a Three-Day Weekend

Welcome to Deale, Maryland, a hidden gem nestled along the Chesapeake Bay! This delightful waterfront town offers a perfect escape for a three-day weekend trip with friends. With its picturesque landscapes, friendly locals, and a plethora of attractions, Deale promises an unforgettable adventure. So, pack your bags and get ready to immerse yourself in the beauty of this coastal paradise.

Day 1: Discover the Natural Beauty

Morning: Breezy Waterfront Stroll at Herrington Harbor South

Start your day with a leisurely stroll along the breathtaking Herrington Harbor South. This marina boasts stunning views of the Chesapeake Bay and is a popular spot for boating enthusiasts. Take in the fresh sea breeze as you wander along the docks, admiring the impressive array of boats and yachts. If you’re feeling adventurous, consider renting a kayak or paddleboard to explore the calm waters.

Lunch: Seafood Galore at Dockside Restaurant

After working up an appetite, head over to Dockside Restaurant, a local favorite known for its delectable seafood dishes. Indulge in their famous Maryland crab cakes, bursting with flavor and served with a side of Old Bay seasoned fries. If you’re craving a taste of the sea, their steamed shrimp or fresh catch of the day won’t disappoint.

Afternoon: Tranquility at Franklin Point State Park

Escape the hustle and bustle of everyday life at Franklin Point State Park. This serene park offers a tranquil setting for a leisurely afternoon in nature. Take a scenic hike along the trails that wind through the lush forest, or find a cozy spot on the beach and bask in the sun. Keep an eye out for various bird species and other wildlife that call this area home.

Dinner: Local Fare at Skippers Pier

For an authentic taste of Deale, head to Skippers Pier for dinner. This waterfront restaurant boasts a relaxed atmosphere and a menu filled with seafood classics. Don’t miss their famous crab soup, a hearty and flavorful delight. Pair it with their perfectly seasoned rockfish, a local favorite, or opt for a mouthwatering steak if seafood isn’t your preference. And of course, save room for their homemade Key lime pie—it’s simply divine!

Day 2: Captivating History and Coastal Charm

Morning: Journey Through History at Historic London Town and Gardens

Start your day by immersing yourself in the rich history of Deale at Historic London Town and Gardens. This living history museum takes you back to the 18th century, showcasing colonial life through well-preserved buildings and beautiful gardens. Take a guided tour to learn about the town’s significance during the colonial era, or simply wander through the gardens, where fragrant blooms and lush greenery create a peaceful ambiance.

Lunch: Coastal Comfort Food at South County Café

After your historical adventure, head to South County Café for a delightful lunch. This charming eatery offers a cozy atmosphere and a menu filled with comforting dishes. Indulge in their famous crab melt sandwich, a heavenly combination of fresh crab meat, melted cheese, and buttery bread. Pair it with a cup of their homemade clam chowder, bursting with creamy goodness.

Afternoon: Relaxation at Chesapeake Beach

Escape to the idyllic Chesapeake Beach for an afternoon of relaxation. Sink your toes into the soft sand, soak up the sun, and swim in the calm waters of the bay. If you’re up for some adventure, consider renting a jet ski or paddleboat to explore the shoreline. Keep an eye out for the stunning sunset—a sight you won’t want to miss.

Dinner: Waterfront Dining at Pirates Cove Restaurant

End your day on a high note with a delightful waterfront dinner at Pirates Cove Restaurant. Known for its stunning views and exceptional seafood, this establishment is a local treasure. Indulge in their famous jumbo lump crab cakes, made with only the freshest ingredients. Pair it with a refreshing cocktail from their extensive menu and savor the flavors while enjoying the panoramic views of the bay.

Day 3: Outdoor Adventures and Local Delights

Morning: Thrilling Watersports at Triton Sea Adventures

Kickstart your day with an adrenaline rush at Triton Sea Adventures. Embark on a thrilling jet ski tour or try your hand at wakeboarding along the Chesapeake Bay. The experienced guides will ensure your safety and provide an unforgettable experience. Feel the wind in your hair as you glide across the water, taking in the stunning natural surroundings.

Lunch: Scenic Picnic at Franklin Point State Park

After your exhilarating morning, head back to Franklin Point State Park for a scenic picnic. Pack a delicious spread of local cheeses, charcuterie, and freshly baked bread from a nearby market. Find a shaded spot with a view of the bay and savor the flavors while relishing the tranquility of nature.

Afternoon: Fishing Excursion with Fish Hawk Charters

Experience the thrill of fishing with Fish Hawk Charters. Join a guided fishing excursion and cast your line in the abundant waters of the Chesapeake Bay. Whether you’re a seasoned angler or a beginner, the experienced captains will guide you to the best fishing spots, increasing your chances of reeling in a memorable catch. Enjoy the camaraderie with your friends as you compete to catch the biggest fish.

Dinner: Rustic Charm at Happy Harbor Restaurant

Conclude your three-day weekend in Deale with a delightful dinner at Happy Harbor Restaurant. This cozy establishment captures the essence of the town with its rustic charm and friendly service. Indulge in their mouthwatering seafood platter, offering a tantalizing variety of freshly caught fish, shrimp, and scallops. For land lovers, their tender prime rib or juicy steak options are equally satisfying. Raise a glass to an unforgettable weekend with their selection of local craft beers or a glass of fine wine.

As your three-day weekend comes to a close, bid farewell to the coastal charm of Deale, Maryland. Reflect on the moments shared with friends, the delicious seafood savored, and the natural beauty that surrounded you. Remember, adventures await just around the corner, and Deale will always welcome you back with open arms.

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